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N,N-Dimethyltryptamine

N,N-Dimethyltryptamine (DMT or N,N-DMT) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms. DMT can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last about five to fifteen minutes. Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (MAOI), such as the ayahuasca brew of many native Amazonian tribes. DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms.

DMT is a functional analog and structural analog of other psychedelic tryptamines such as O-acetylpsilocin (4-AcO-DMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), NB-DMT, O-methylbufotenin (5-MeO-DMT), and bufotenin (5-HO-DMT). Parts of the structure of DMT occur within some important biomolecules like serotonin and melatonin, making them structural analogs of DMT.

Human consumption
DMT is produced in many species of plants often in conjunction with its close chemical relatives 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and bufotenin (5-OH-DMT). DMT-containing plants are commonly used in indigenous Amazonian shamanic practices. It is usually one of the main active constituents of the drink ayahuasca; however, ayahuasca is sometimes brewed with plants that do not produce DMT. It occurs as the primary psychoactive alkaloid in several plants including Mimosa tenuiflora, Diplopterys cabrerana, and Psychotria viridis. DMT is found as a minor alkaloid in snuff made from Virola bark resin in which 5-MeO-DMT is the main active alkaloid. DMT is also found as a minor alkaloid in bark, pods, and beans of Anadenanthera peregrina and Anadenanthera colubrina used to make Yopo and Vilca snuff, in which bufotenin is the main active alkaloid. Psilocin and psilocybin, the main psychoactive compounds in psilocybin mushrooms, are structurally similar to DMT.

The psychotropic effects of DMT were first studied scientifically by the Hungarian chemist and psychologist Stephen Szára, who performed research with volunteers in the mid-1950s. Szára, who later worked for the United States National Institutes of Health, had turned his attention to DMT after his order for LSD from the Swiss company Sandoz Laboratories was rejected on the grounds that the powerful psychotropic could be dangerous in the hands of a communist country.

DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor such as a reversible inhibitor of monoamine oxidase A (RIMA), for example, harmaline. Without a MAOI, the body quickly metabolizes orally administered DMT, and it therefore has no hallucinogenic effect unless the dose exceeds the body's monoamine oxidase's metabolic capacity. Other means of consumption such as vaporizing, injecting, or insufflating the drug can produce powerful hallucinations for a short time (usually less than half an hour), as the DMT reaches the brain before it can be metabolized by the body's natural monoamine oxidase. Taking an MAOI prior to vaporizing or injecting DMT prolongs and enhances the effects.

Clinical use research
Existing research on clinical use of DMT mostly focuses on its effects when exogenously administered as a drug. Although the scientific consensus is that DMT is naturally occurring molecule in humans, the effects of endogenous DMT in humans (and more broadly in mammals) is still not well understood.

Dimethyltryptamine (DMT), an endogenous ligand of sigma-1 receptors (Sig-1Rs), acts against systemic hypoxia. Research demonstrates DMT reduces the number of apoptotic and ferroptotic cells in mammalian forebrain and supports astrocyte survival in an ischemic environment. According to these data, DMT may be considered as adjuvant pharmacological therapy in the management of acute cerebral ischemia.

DMT is studied as a potential treatment for Parkinson's disease in a Phase 1/2 clinical trial.

SPL026 (DMT fumarate) is currently undergoing phase II clinical trials investigating its use alongside supportive psychotherapy as a potential treatment for major depressive disorder. Additionally, a safety study is underway to investigate the effects of combining SSRIs with SPL026.

Neuropharmacology
Recently, researchers discovered that N,N-dimethyltryptamine is a potent psychoplastogen, a compound capable of promoting rapid and sustained neuroplasticity that may have wide-ranging therapeutic benefit.

Quantities of dimethyltryptamine and O-methylbufotenin were found present in the cerebrospinal fluid of humans in a psychiatric study.

Subjective psychedelic experiences
Subjective experiences of DMT includes profound time-dilatory, visual, auditory, tactile, and proprioceptive distortions and hallucinations, and other experiences that, by most firsthand accounts, defy verbal or visual description. Examples include perceiving hyperbolic geometry or seeing Escher-like impossible objects.

Several scientific experimental studies have tried to measure subjective experiences of altered states of consciousness induced by drugs under highly controlled and safe conditions.

Rick Strassman and his colleagues conducted a five-year-long DMT study at the University of New Mexico in the 1990s. The results provided insight about the quality of subjective psychedelic experiences. In this study participants received the DMT dosage via intravenous injection and the findings suggested that different psychedelic experiences can occur, depending on the level of dosage. Lower doses (0.01 and 0.05 mg/kg) produced some aesthetic and emotional responses, but not hallucinogenic experiences (e.g., 0.05 mg/kg had mild mood elevating and calming properties). In contrast, responses produced by higher doses (0.2 and 0.4 mg/kg) researchers labeled as "hallucinogenic" that elicited "intensely colored, rapidly moving display of visual images, formed, abstract or both". Comparing to other sensory modalities, the most affected was the visual. Participants reported visual hallucinations, fewer auditory hallucinations and specific physical sensations progressing to a sense of bodily dissociation, as well as to experiences of euphoria, calm, fear, and anxiety. These dose-dependent effects match well with anonymously posted "trip reports" online, where users report "breakthroughs" above certain doses.

Strassman also stressed the importance of the context where the drug has been taken. He claimed that DMT has no beneficial effects of itself, rather the context when and where people take it plays an important role.

It appears that DMT can induce a state or feeling wherein the person believes to "communicate with other intelligent lifeforms" (see "machine elves"). High doses of DMT produce a state that involves a sense of "another intelligence" that people sometimes describe as "super-intelligent", but "emotionally detached".

A 1995 study by Adolf Dittrich and Daniel Lamparter found that the DMT-induced altered state of consciousness (ASC) is strongly influenced by habitual rather than situative factors. In the study, researchers used three dimensions of the APZ questionnaire to examine ASC. The first dimension, oceanic boundlessness (OB), refers to dissolution of ego boundaries and is mostly associated with positive emotions. The second dimension, anxious ego-dissolution (AED), represents a disordering of thoughts and decreases in autonomy and self-control. Last, visionary restructuralization (VR) refers to auditory/visual illusions and hallucinations. Results showed strong effects within the first and third dimensions for all conditions, especially with DMT, and suggested strong intrastability of elicited reactions independently of the condition for the OB and VR scales.

Reported encounters with external entities
Entities perceived during DMT inebriation have been represented in diverse forms of psychedelic art. The term machine elf was coined by ethnobotanist Terence McKenna for the entities he encountered in DMT "hyperspace", also using terms like fractal elves, or self-transforming machine elves. McKenna first encountered the "machine elves" after smoking DMT in Berkeley in 1965. His subsequent speculations regarding the hyperdimensional space in which they were encountered have inspired a great many artists and musicians, and the meaning of DMT entities has been a subject of considerable debate among participants in a networked cultural underground, enthused by McKenna's effusive accounts of DMT hyperspace. Cliff Pickover has also written about the "machine elf" experience, in the book Sex, Drugs, Einstein, & Elves. Strassman noted similarities between self-reports of his DMT study participants' encounters with these "entities", and mythological descriptions of figures such as Ḥayyot haq-Qodesh in ancient religions, including both angels and demons. Strassman also argues for a similarity in his study participants' descriptions of mechanized wheels, gears and machinery in these encounters, with those described in visions of encounters with the Living Creatures and Ophanim of the Hebrew Bible, noting they may stem from a common neuropsychopharmacological experience.

Strassman argues that the more positive of the "external entities" encountered in DMT experiences should be understood as analogous to certain forms of angels: "The medieval Jewish philosophers whom I rely upon for understanding the Hebrew Bible text and its concept of prophecy portray angels as God's intermediaries. That is, they perform a certain function for God. Within the context of my DMT research, I believe that the beings that volunteers see could be conceived of as angelic – that is, previously invisible, incorporeal spiritual forces that are engarbed or enclothed in a particular form – determined by the psychological and spiritual development of the volunteers – bringing a particular message or experience to that volunteer." Strassman's experimental participants also note that some other entities can subjectively resemble creatures more like insects and aliens. As a result, Strassman writes these experiences among his experimental participants "also left me feeling confused and concerned about where the spirit molecule was leading us. It was at this point that I began to wonder if I was getting in over my head with this research."

Hallucinations of strange creatures had been reported by Stephen Szara in a 1958 study in psychotic patients, in which he described how one of his subjects under the influence of DMT had experienced "strange creatures, dwarves or something" at the beginning of a DMT trip.

Other researchers of the entities seemingly encountered by DMT users describe them as "entities" or "beings" in humanoid as well as animal form, with descriptions of "little people" being common (non-human gnomes, elves, imps, etc.). Strassman and others have speculated that this form of hallucination may be the cause of alien abduction and extraterrestrial encounter experiences, which may occur through endogenously-occurring DMT.

Likening them to descriptions of rattling and chattering auditory phenomena described in encounters with the Hayyoth in the Book of Ezekiel, Rick Strassman notes that participants in his studies, when reporting encounters with the alleged entities, have also described loud auditory hallucinations, such as one subject reporting typically "the elves laughing or talking at high volume, chattering, twittering".

Near-death experience
A 2018 study found significant relationships between a DMT experience and a near-death experience (NDE). A 2019 large-scale study pointed that ketamine, Salvia divinorum, and DMT (and other classical psychedelic substances) may be linked to near-death experiences due to the semantic similarity of reports associated with the use of psychoactive compounds and NDE narratives, but the study concluded that with the current data it is neither possible to corroborate nor refute the hypothesis that the release of an endogenous ketamine-like neuroprotective agent underlies NDE phenomenology.

Physiological response
According to a dose-response study in human subjects, dimethyltryptamine administered intravenously slightly elevated blood pressure, heart rate, pupil diameter, and rectal temperature, in addition to elevating blood concentrations of beta-endorphin, corticotropin, cortisol, and prolactin; growth hormone blood levels rise equally in response to all doses of DMT, and melatonin levels were unaffected."

Conjecture regarding endogenous effects
In the 1950s, the endogenous production of psychoactive agents was considered to be a potential explanation for the hallucinatory symptoms of some psychiatric diseases; this is known as the transmethylation hypothesis. Several speculative and yet untested hypotheses suggest that endogenous DMT is produced in the human brain and is involved in certain psychological and neurological states. DMT is naturally occurring in small amounts in rat brains, human cerebrospinal fluid, and other tissues of humans and other mammals. Further, mRNA for the enzyme necessary for the production of DMT, INMT, are expressed in the human cerebral cortex, choroid plexus, and pineal gland, suggesting an endogenous role in the human brain. In 2011, Nicholas V. Cozzi, of the University of Wisconsin School of Medicine and Public Health, concluded that INMT, an enzyme that is associated with the biosynthesis of DMT and endogenous hallucinogens, is present in the primate (rhesus macaque) pineal gland, retinal ganglion neurons, and spinal cord. Neurobiologist Andrew Gallimore (2013) suggested that while DMT might not have a modern neural function, it may have been an ancestral neuromodulator once secreted in psychedelic concentrations during REM sleep, a function now lost.

Mental disorders
DMT may trigger psychological reactions, known colloquially as a "bad trip", such as intense fear, paranoia, anxiety, panic attacks, and substance-induced psychosis, particularly in predisposed individuals.

Addiction and dependence liability
DMT, like other serotonergic psychedelics, is considered to be non-addictive with low abuse potential. A study examining substance use disorder for DSM-IV reported that almost no hallucinogens produced dependence, unlike psychoactive drugs of other classes such as stimulants and depressants. At present, there have been no studies that report drug withdrawal syndrome with termination of DMT, and dependence potential of DMT and the risk of sustained psychological disturbance may be minimal when used infrequently; however, the physiological dependence potential of DMT and ayahuasca has not yet been documented convincingly.

Tolerance
Unlike other classical psychedelics, studies report that DMT did not exhibit tolerance upon repeated administration of twice a day sessions, separated by 5 hours, for 5 consecutive days; field reports suggests a refractory period of only 15 to 30 minutes, while the plasma levels of DMT was nearly undetectable 30 minutes after intravenous administration. Another study of four closely spaced DMT infusion sessions with 30 minute intervals also suggests no tolerance buildup to the psychological effects of the compound, while heart rate responses and neuroendocrine effects were diminished with repeated administration. A fully hallucinogenic dose of DMT did not demonstrate cross-tolerance to human subjects who are highly tolerant to LSD; researches suggest that DMT exhibits unique pharmacological properties compared to other classical psychedelics.

Long-term use
There have been no serious adverse effects reported on long-term use of DMT, apart from acute cardiovascular events. Repeated and one-time administration of DMT produces marked changes in the cardiovascular system, with an increase in systolic and diastolic blood pressure; although the changes were not statistically significant, a robust trend towards significance was observed for systolic blood pressure at high doses.

Drug-interactions
DMT is inactive when ingested orally due to metabolism by MAO, and DMT-containing drinks such as ayahuasca have been found to contain MAOIs, in particular, harmine and harmaline. Life-threatening lethalities such as serotonin syndrome (SS) may occur when MAOIs are combined with certain serotonergic medications such as SSRI antidepressants. Serotonin syndrome has also been reported with tricyclic antidepressants, opiates, analgesic, and antimigraine drugs; it is advised to exercise caution when an individual had used dextromethorphan (DXM), MDMA, ginseng, or St. John's wort recently.

Chronic use of SSRIs, TCAs, and MAOIs diminish subjective effects of psychedelics due to presumed SSRI-induced 5-HT2A receptors downregulation and MAOI-induced 5-HT2A receptor desensitization. The interaction between psychedelics and antipsychotics and anticonvulsant are not well documented, however reports reveal that co-use of psychedelics with mood stabilizers such as lithium may provoke seizure and dissociative effects in individuals with bipolar disorder.

Inhalation
A standard dose for vaporized DMT is 20–60 milligrams, depending highly on the efficiency of vaporization as well as body weight and personal variation. In general, this is inhaled in a few successive breaths, but lower doses can be used if the user can inhale it in fewer breaths (ideally one). The effects last for a short period of time, usually 5 to 15 minutes, dependent on the dose. The onset after inhalation is very fast (less than 45 seconds) and peak effects are reached within a minute. In the 1960s, DMT was known as a "businessman's trip" in the US because of the relatively short duration (and rapid onset) of action when inhaled. DMT can be inhaled using a bong, typically when sandwiched between layers of plant matter, using a specially designed pipe, or by using an e-cigarette once it has been dissolved in propylene glycol and/or vegetable glycerin. Some users have also started using vaporizers meant for cannabis extracts ("wax pens") for ease of temperature control when vaporizing crystals. A DMT-infused smoking blend is called Changa, and is typically used in pipes or other utensils meant for smoking dried plant matter.

Intravenous injection
In a study conducted from 1990 through 1995, University of New Mexico psychiatrist Rick Strassman found that some volunteers injected with high doses of DMT reported experiences with perceived alien entities. Usually, the reported entities were experienced as the inhabitants of a perceived independent reality that the subjects reported visiting while under the influence of DMT.

Oral
DMT is broken down by the enzyme monoamine oxidase through a process called deamination, and is quickly inactivated orally unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American beverage ayahuasca is derived by boiling Banisteriopsis caapi with leaves of one or more plants containing DMT, such as Psychotria viridis, Psychotria carthagenensis, or Diplopterys cabrerana. The Banisteriopsis caapi contains harmala alkaloids, a highly active reversible inhibitor of monoamine oxidase A (RIMAs), rendering the DMT orally active by protecting it from deamination. A variety of different recipes are used to make the brew depending on the purpose of the ayahuasca session, or local availability of ingredients. Two common sources of DMT in the western US are reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids but also contain gramine, which is toxic and difficult to separate. In addition, Jurema (Mimosa tenuiflora) shows evidence of DMT content: the pink layer in the inner rootbark of this small tree contains a high concentration of N,N-DMT.

Taken orally with an RIMA, DMT produces a long-lasting (over three hours), slow, deep metaphysical experience similar to that of psilocybin mushrooms, but more intense.

The intensity of orally administered DMT depends on the type and dose of MAOI administered alongside it. When ingested with 120 mg of harmine (a RIMA and member of the harmala alkaloids), 20 mg of DMT was reported to have psychoactive effects by author and ethnobotanist Jonathan Ott. Ott reported that to produce a visionary state, the threshold oral dose was 30 mg DMT alongside 120 mg harmine. This is not necessarily indicative of a standard dose, as dose-dependent effects may vary due to individual variations in drug metabolism.

History
Naturally occurring substances (of both vegetable and animal origin) containing DMT have been used in South America since pre-Columbian times.

DMT was first synthesized in 1931 by Canadian chemist Richard Helmuth Fredrick Manske. In general, its discovery as a natural product is credited to Brazilian chemist and microbiologist Oswaldo Gonçalves de Lima, who isolated an alkaloid he named nigerina (nigerine) from the root bark of Mimosa tenuiflora in 1946. However, in a careful review of the case Jonathan Ott shows that the empirical formula for nigerine determined by Gonçalves de Lima, which notably contains an atom of oxygen, can match only a partial, "impure" or "contaminated" form of DMT. It was only in 1959, when Gonçalves de Lima provided American chemists a sample of Mimosa tenuiflora roots, that DMT was unequivocally identified in this plant material. Less ambiguous is the case of isolation and formal identification of DMT in 1955 in seeds and pods of Anadenanthera peregrina by a team of American chemists led by Evan Horning (1916–1993). Since 1955, DMT has been found in a number of organisms: in at least fifty plant species belonging to ten families, and in at least four animal species, including one gorgonian and three mammalian species (including humans).

In terms of a scientific understanding, the hallucinogenic properties of DMT were not uncovered until 1956 by Hungarian chemist and psychiatrist Stephen Szara. In his paper "Dimethyltryptamin: Its Metabolism in Man; the Relation of its Psychotic Effect to the Serotonin Metabolism", Szara employed synthetic DMT, synthesized by the method of Speeter and Anthony, which was then administered to 20 volunteers by intramuscular injection. Urine samples were collected from these volunteers for the identification of DMT metabolites. This is considered to be the converging link between the chemical structure DMT to its cultural consumption as a psychoactive and religious sacrament.

Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine Banisteriopsis caapi to make ayahuasca decoctions. In 1957, American chemists Francis Hochstein and Anita Paradies identified DMT in an "aqueous extract" of leaves of a plant they named Prestonia amazonicum [sic] and described as "commonly mixed" with B. caapi. The lack of a proper botanical identification of Prestonia amazonica in this study led American ethnobotanist Richard Evans Schultes (1915–2001) and other scientists to raise serious doubts about the claimed plant identity. The mistake likely led the writer William Burroughs to regard the DMT he experimented with in Tangier in 1961 as "Prestonia". Better evidence was produced in 1965 by French pharmacologist Jacques Poisson, who isolated DMT as a sole alkaloid from leaves, provided and used by Aguaruna Indians, identified as having come from the vine Diplopterys cabrerana (then known as Banisteriopsis rusbyana). Published in 1970, the first identification of DMT in the plant Psychotria viridis, another common additive of ayahuasca, was made by a team of American researchers led by pharmacologist Ara der Marderosian. Not only did they detect DMT in leaves of P. viridis obtained from Kaxinawá indigenous people, but they also were the first to identify it in a sample of an ayahuasca decoction, prepared by the same indigenous people.

International law
Internationally DMT is illegal, but ayahuasca and DMT brews and preparations are lawful. DMT is controlled by the Convention on Psychotropic Substances at the international level. The Convention makes it illegal to possess, buy, purchase, sell, to retail and to dispense without a licence.

By country and continent
In some countries, ayahuasca is a forbidden or controlled or regulated substance, while in other countries it is not a controlled substance or its production, consumption, and sale, is allowed to various degrees.

Asia

 * Israel – DMT is an illegal substance; production, trade and possession are prosecuted as crimes.
 * India – DMT is illegal to produce, transport, trade in or possess with a minimum prison or jail punishment of ten years.

Europe

 * France – DMT, along with most of its plant sources, is classified as a stupéfiant (narcotic).
 * Germany – DMT is prohibited as a class I drug.
 * Republic of Ireland – DMT is an illegal Schedule 1 drug under the Misuse of Drugs Acts. An attempt in 2014 by a member of the Santo Daime church to gain a religious exemption to import the drug failed.
 * Latvia — DMT is prohibited as a Schedule I drug.
 * Netherlands – The drug is banned as it is classified as a List 1 Drug per the Opium Law. Production, trade and possession of DMT are prohibited.
 * Russia – Classified as a Schedule I narcotic, including its derivatives (see sumatriptan and zolmitriptan).
 * Serbia – DMT, along with stereoisomers and salts is classified as List 4 (Psychotropic substances) substance according to Act on Control of Psychoactive Substances.
 * Sweden – DMT is considered a Schedule 1 drug. The Swedish supreme court concluded in 2018 that possession of processed plant material containing a significant amount of DMT is illegal. However, possession of unprocessed such plant material was ruled legal.
 * United Kingdom – DMT is classified as a Class A drug.
 * Belgium – DMT cannot be possessed, sold, purchased or imported. Usage is not specifically prohibited, but since usage implies possession one could be prosecuted that way.

North America

 * Canada – DMT is classified as a Schedule III drug under the Controlled Drugs and Substances Act, but is legal for religious groups to use. In 2017 the Santo Daime Church Céu do Montréal received religious exemption to use Ayahuasca as a sacrament in their rituals.

 * United States – DMT is classified in the United States as a Schedule I drug under the Controlled Substances Act of 1970.

In December 2004, the Supreme Court lifted a stay, thereby allowing the Brazil-based União do Vegetal (UDV) church to use a decoction containing DMT in their Christmas services that year. This decoction is a tea made from boiled leaves and vines, known as hoasca within the UDV, and ayahuasca in different cultures. In Gonzales v. O Centro Espírita Beneficente União do Vegetal, the Supreme Court heard arguments on 1 November 2005, and unanimously ruled in February 2006 that the U.S. federal government must allow the UDV to import and consume the tea for religious ceremonies under the 1993 Religious Freedom Restoration Act.

In September 2008, the three Santo Daime churches filed suit in federal court to gain legal status to import DMT-containing ayahuasca tea. The case, Church of the Holy Light of the Queen v. Mukasey, presided over by U.S. District Judge Owen M. Panner, was ruled in favor of the Santo Daime church. As of 21 March 2009, a federal judge says members of the church in Ashland can import, distribute and brew ayahuasca. Panner issued a permanent injunction barring the government from prohibiting or penalizing the sacramental use of "Daime tea". Panner's order said activities of The Church of the Holy Light of the Queen are legal and protected under freedom of religion. His order prohibits the federal government from interfering with and prosecuting church members who follow a list of regulations set out in his order.

Oceania

 * New Zealand – DMT is classified as a Class A drug under the Misuse of Drugs Act 1975.
 * Australia – DMT is listed as a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO."                                                                                Between 2011 and 2012, the Australian federal government was considering changes to the Australian Criminal Code that would classify any plants containing any amount of DMT as "controlled plants". DMT itself was already controlled under current laws. The proposed changes included other similar blanket bans for other substances, such as a ban on any and all plants containing mescaline or ephedrine. The proposal was not pursued after political embarrassment on realisation that this would make the official Floral Emblem of Australia, Acacia pycnantha (Golden Wattle), illegal. The Therapeutic Goods Administration and federal authority had considered a motion to ban the same, but this was withdrawn in May 2012 (as DMT may still hold potential entheogenic value to native and/or religious people).                                                                                Under the Misuse of Drugs Act 1981 6.0 g (3/16 oz) of DMT is considered enough to determine a court of trial and 2.0 g (1/16 oz) is considered intent to sell and supply.

Chemistry
DMT is commonly handled and stored as a hemifumarate,  as other DMT acid salts are extremely hygroscopic and will not readily crystallize. Its freebase form, although less stable than DMT hemifumarate, is favored by recreational users choosing to vaporize the chemical as it has a lower boiling point.

Biosynthesis
Dimethyltryptamine is an indole alkaloid derived from the shikimate pathway. Its biosynthesis is relatively simple and summarized in the adjacent picture. In plants, the parent amino acid -tryptophan is produced endogenously where in animals -tryptophan is an essential amino acid coming from diet. No matter the source of -tryptophan, the biosynthesis begins with its decarboxylation by an aromatic amino acid decarboxylase (AADC) enzyme (step 1). The resulting decarboxylated tryptophan analog is tryptamine. Tryptamine then undergoes a transmethylation (step 2): the enzyme indolethylamine-N-methyltransferase (INMT) catalyzes the transfer of a methyl group from cofactor S-adenosylmethionine (SAM), via nucleophilic attack, to tryptamine. This reaction transforms SAM into S-adenosylhomocysteine (SAH), and gives the intermediate product N-methyltryptamine (NMT). NMT is in turn transmethylated by the same process (step 3) to form the end product N,N-dimethyltryptamine. Tryptamine transmethylation is regulated by two products of the reaction: SAH,  and DMT  were shown ex vivo to be among the most potent inhibitors of rabbit INMT activity.

This transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of SAM methyl group with carbon-14 ((14C-CH3)SAM).

Laboratory synthesis
DMT can be synthesized through several possible pathways from different starting materials. The two most commonly encountered synthetic routes are through the reaction of indole with oxalyl chloride followed by reaction with dimethylamine and reduction of the carbonyl functionalities with lithium aluminium hydride to form DMT. The second commonly encountered route is through the N,N-dimethylation of tryptamine using formaldehyde followed by reduction with sodium cyanoborohydride or sodium triacetoxyborohydride. Sodium borohydride can be used but requires a larger excess of reagents and lower temperatures due to it having a higher selectivity for carbonyl groups as opposed to imines. Procedures using sodium cyanoborohydride and sodium triacetoxyborohydride (presumably created in situ from cyanoborohydride though this may not be the case due to the presence of water or methanol) also result in the creation of cyanated tryptamine and beta-carboline byproducts of unknown toxicity while using sodium borohydride in absence of acid does not. Bufotenine, a plant extract, can also be synthesized into DMT.

Alternatively, an excess of methyl iodide or methyl p-toluenesulfonate and sodium carbonate can be used to over-methylate tryptamine, resulting in the creation of a quaternary ammonium salt, which is then dequaternized (demethylated) in ethanolamine to yield DMT. The same two-step procedure is used to synthesize other N,N-dimethylated compounds, such as 5-MeO-DMT.

Clandestine manufacture
In a clandestine setting, DMT is not typically synthesized due to the lack of availability of the starting materials, namely tryptamine and oxalyl chloride. Instead, it is more often extracted from plant sources using a nonpolar hydrocarbon solvent such as naphtha or heptane, and a base such as sodium hydroxide.

Alternatively, an acid–base extraction is sometimes used instead.

A variety of plants contain DMT at sufficient levels for being viable sources, but specific plants such as Mimosa tenuiflora, Acacia acuminata and Acacia confusa are most often used.

The chemicals involved in the extraction are commonly available. The plant material may be illegal to procure in some countries. The end product (DMT) is illegal in most countries.

Evidence in mammals
Published in Science in 1961, Julius Axelrod found an N-methyltransferase enzyme capable of mediating biotransformation of tryptamine into DMT in a rabbit's lung. This finding initiated a still ongoing scientific interest in endogenous DMT production in humans and other mammals. From then on, two major complementary lines of evidence have been investigated: localization and further characterization of the N-methyltransferase enzyme, and analytical studies looking for endogenously produced DMT in body fluids and tissues.

In 2013, researchers reported DMT in the pineal gland microdialysate of rodents.

A study published in 2014 reported the biosynthesis of N,N-dimethyltryptamine (DMT) in the human melanoma cell line SK-Mel-147 including details on its metabolism by peroxidases. It is assumed that more than half of the amount of DMT produced by the acidophilic cells of the pineal gland is secreted before and during death, the amount being 2.5–3.4 mg/kg. However, this claim by Strassman has been criticized by David Nichols who notes that DMT does not appear to be produced in any meaningful amount by the pineal gland. Removal or calcification of the pineal gland does not induce any of the symptoms caused by removal of DMT. The symptoms presented are consistent solely with reduction in melatonin, which is the pineal gland's known function. Nichols instead suggests that dynorphin and other endorphins are responsible for the reported euphoria experienced by patients during a near-death experience. In 2014, researchers demonstrated the immunomodulatory potential of DMT and 5-MeO-DMT through the Sigma-1 receptor of human immune cells. This immunomodulatory activity may contribute to significant anti-inflammatory effects and tissue regeneration.

Endogenous DMT
N,N-Dimethyltryptamine (DMT), a psychedelic compound identified endogenously in mammals, is biosynthesized by aromatic -amino acid decarboxylase (AADC) and indolethylamine-N-methyltransferase (INMT). Studies have investigated brain expression of INMT transcript in rats and humans, coexpression of INMT and AADC mRNA in rat brain and periphery, and brain concentrations of DMT in rats. INMT transcripts were identified in the cerebral cortex, pineal gland, and choroid plexus of both rats and humans via in situ hybridization. Notably, INMT mRNA was colocalized with AADC transcript in rat brain tissues, in contrast to rat peripheral tissues where there existed little overlapping expression of INMT with AADC transcripts. Additionally, extracellular concentrations of DMT in the cerebral cortex of normal behaving rats, with or without the pineal gland, were similar to those of canonical monoamine neurotransmitters including serotonin. A significant increase of DMT levels in the rat visual cortex was observed following induction of experimental cardiac arrest, a finding independent of an intact pineal gland. These results show for the first time that the rat brain is capable of synthesizing and releasing DMT at concentrations comparable to known monoamine neurotransmitters and raise the possibility that this phenomenon may occur similarly in human brains.

The first claimed detection of mammalian endogenous DMT was published in June 1965: German researchers F. Franzen and H. Gross report to have evidenced and quantified DMT, along with its structural analog bufotenin (5-HO-DMT), in human blood and urine. In an article published four months later, the method used in their study was strongly criticized, and the credibility of their results challenged.

Few of the analytical methods used prior to 2001 to measure levels of endogenously formed DMT had enough sensitivity and selectivity to produce reliable results. Gas chromatography, preferably coupled to mass spectrometry (GC-MS), is considered a minimum requirement. A study published in 2005 implements the most sensitive and selective method ever used to measure endogenous DMT: liquid chromatography–tandem mass spectrometry with electrospray ionization (LC-ESI-MS/MS) allows for reaching limits of detection (LODs) 12 to 200 fold lower than those attained by the best methods employed in the 1970s. The data summarized in the table below are from studies conforming to the abovementioned requirements (abbreviations used: CSF = cerebrospinal fluid; LOD = limit of detection; n = number of samples; ng/L and ng/kg = nanograms (10−9 g) per litre, and nanograms per kilogram, respectively):

A 2013 study found DMT in microdialysate obtained from a rat's pineal gland, providing evidence of endogenous DMT in the mammalian brain. In 2019 experiments showed that the rat brain is capable of synthesizing and releasing DMT. These results raise the possibility that this phenomenon may occur similarly in human brains.

Detection in body fluids
DMT may be measured in blood, plasma or urine using chromatographic techniques as a diagnostic tool in clinical poisoning situations or to aid in the medicolegal investigation of suspicious deaths. In general, blood or plasma DMT levels in recreational users of the drug are in the 10–30 μg/L range during the first several hours post-ingestion. Less than 0.1% of an oral dose is eliminated unchanged in the 24-hour urine of humans.

INMT
Before techniques of molecular biology were used to localize indolethylamine N-methyltransferase (INMT), characterization and localization went on a par: samples of the biological material where INMT is hypothesized to be active are subject to enzyme assay. Those enzyme assays are performed either with a radiolabeled methyl donor like (14C-CH3)SAM to which known amounts of unlabeled substrates like tryptamine are added or with addition of a radiolabeled substrate like (14C)NMT to demonstrate in vivo formation. As qualitative determination of the radioactively tagged product of the enzymatic reaction is sufficient to characterize INMT existence and activity (or lack of), analytical methods used in INMT assays are not required to be as sensitive as those needed to directly detect and quantify the minute amounts of endogenously formed DMT. The essentially qualitative method thin layer chromatography (TLC) was thus used in a vast majority of studies. Also, robust evidence that INMT can catalyze transmethylation of tryptamine into NMT and DMT could be provided with reverse isotope dilution analysis coupled to mass spectrometry for rabbit and human lung during the early 1970s.

Selectivity rather than sensitivity proved to be a challenge for some TLC methods with the discovery in 1974–1975 that incubating rat blood cells or brain tissue with (14C-CH3)SAM and NMT as substrate mostly yields tetrahydro-β-carboline derivatives, and negligible amounts of DMT in brain tissue. It is indeed simultaneously realized that the TLC methods used thus far in almost all published studies on INMT and DMT biosynthesis are incapable to resolve DMT from those tetrahydro-β-carbolines. These findings are a blow for all previous claims of evidence of INMT activity and DMT biosynthesis in avian and mammalian brain, including in vivo,  as they all relied upon use of the problematic TLC methods: their validity is doubted in replication studies that make use of improved TLC methods, and fail to evidence DMT-producing INMT activity in rat and human brain tissues. Published in 1978, the last study attempting to evidence in vivo INMT activity and DMT production in brain (rat) with TLC methods finds biotransformation of radiolabeled tryptamine into DMT to be real but "insignificant". Capability of the method used in this latter study to resolve DMT from tetrahydro-β-carbolines is questioned later.

To localize INMT, a qualitative leap is accomplished with use of modern techniques of molecular biology, and of immunohistochemistry. In humans, a gene encoding INMT is determined to be located on chromosome 7. Northern blot analyses reveal INMT messenger RNA (mRNA) to be highly expressed in rabbit lung, and in human thyroid, adrenal gland, and lung. Intermediate levels of expression are found in human heart, skeletal muscle, trachea, stomach, small intestine, pancreas, testis, prostate, placenta, lymph node, and spinal cord. Low to very low levels of expression are noted in rabbit brain, and human thymus, liver, spleen, kidney, colon, ovary, and bone marrow. INMT mRNA expression is absent in human peripheral blood leukocytes, whole brain, and in tissue from seven specific brain regions (thalamus, subthalamic nucleus, caudate nucleus, hippocampus, amygdala, substantia nigra, and corpus callosum). Immunohistochemistry showed INMT to be present in large amounts in glandular epithelial cells of small and large intestines. In 2011, immunohistochemistry revealed the presence of INMT in primate nervous tissue including retina, spinal cord motor neurons, and pineal gland. A 2020 study using in-situ hybridization, a far more accurate tool than the northern blot analysis, found mRNA coding for INMT expressed in the human cerebral cortex, choroid plexus, and pineal gland.

Pharmacokinetics
DMT peak level concentrations (Cmax) measured in whole blood after intramuscular (IM) injection (0.7 mg/kg, n = 11) and in plasma following intravenous (IV) administration (0.4 mg/kg, n = 10) of fully psychedelic doses are in the range of around 14 to 154 μg/L and 32 to 204 μg/L, respectively. The corresponding molar concentrations of DMT are therefore in the range of 0.074–0.818 μmol/L in whole blood and 0.170–1.08 μmol in plasma. However, several studies have described active transport and accumulation of DMT into rat and dog brains following peripheral administration. Similar active transport, and accumulation processes likely occur in human brains and may concentrate DMT in brain by several-fold or more (relatively to blood), resulting in local concentrations in the micromolar or higher range. Such concentrations would be commensurate with serotonin brain tissue concentrations, which have been consistently determined to be in the 1.5–4 μmol/L range.

Closely coextending with peak psychedelic effects, mean time to reach peak concentrations (Tmax) was determined to be 10–15 minutes in whole blood after IM injection, and 2 minutes in plasma after IV administration. When taken orally mixed in an ayahuasca decoction, and in freeze-dried ayahuasca gel caps, DMT Tmax is considerably delayed: 107.59 ± 32.5 minutes, and 90–120 minutes, respectively. The pharmacokinetics for vaporizing DMT have not been studied or reported.

Neurogenesis
In September 2020, an in vitro and in vivo study showed that DMT present in the ayahuasca infusion promotes neurogenesis.

Pharmacodynamics
DMT binds non-selectively with affinities below 0.6 μmol/L to the following serotonin receptors: 5-HT1A,  5-HT1B, 5-HT1D,   5-HT2A,   5-HT2B,  5-HT2C,   5-HT6,  and 5-HT7. An agonist action has been determined at 5-HT1A, 5-HT2A and 5-HT2C. Its efficacies at other serotonin receptors remain to be determined. Of special interest will be the determination of its efficacy at human 5-HT2B receptor as two in vitro assays evidenced DMT's high affinity for this receptor: 0.108 μmol/L and 0.184 μmol/L. This may be of importance because chronic or frequent uses of serotonergic drugs showing preferential high affinity and clear agonism at 5-HT2B receptor have been causally linked to valvular heart disease.

It has also been shown to possess affinity for the dopamine D1, α1-adrenergic, α2-adrenergic, imidazoline-1, and σ1 receptors. Converging lines of evidence established activation of the σ1 receptor at concentrations of 50–100 μmol/L. Its efficacies at the other receptor binding sites are unclear. It has also been shown in vitro to be a substrate for the cell-surface serotonin transporter (SERT) expressed in human platelets, and the rat vesicular monoamine transporter 2 (VMAT2), which was transiently expressed in fall armyworm Sf9 cells. DMT inhibited SERT-mediated serotonin uptake into platelets at an average concentration of 4.00 ± 0.70 μmol/L and VMAT2-mediated serotonin uptake at an average concentration of 93 ± 6.8 μmol/L.

As with other so-called "classical hallucinogens", a large part of DMT psychedelic effects can be attributed to a functionally selective activation of the 5-HT2A receptor. DMT concentrations eliciting 50% of its maximal effect (half maximal effective concentration = EC50) at the human 5-HT2A receptor in vitro are in the 0.118–0.983 μmol/L range. This range of values coincides well with the range of concentrations measured in blood and plasma after administration of a fully psychedelic dose (see Pharmacokinetics).

As DMT has been shown to have slightly better efficacy (EC50) at human serotonin 2C receptor than at the 2A receptor, 5-HT2C is also likely implicated in DMT's overall effects. Other receptors such as 5-HT1A  and σ1 may also play a role.

In 2009, it was hypothesized that DMT may be an endogenous ligand for the σ1 receptor. The concentration of DMT needed for σ1 activation in vitro (50–100 μmol/L) is similar to the behaviorally active concentration measured in mouse brain of approximately 106 μmol/L This is minimally 4 orders of magnitude higher than the average concentrations measured in rat brain tissue or human plasma under basal conditions (see Endogenous DMT), so σ1 receptors are likely to be activated only under conditions of high local DMT concentrations. If DMT is stored in synaptic vesicles, such concentrations might occur during vesicular release. To illustrate, while the average concentration of serotonin in brain tissue is in the 1.5–4 μmol/L range, the concentration of serotonin in synaptic vesicles was measured at 270 mM. Following vesicular release, the resulting concentration of serotonin in the synaptic cleft, to which serotonin receptors are exposed, is estimated to be about 300 μmol/L. Thus, while in vitro receptor binding affinities, efficacies, and average concentrations in tissue or plasma are useful, they are not likely to predict DMT concentrations in the vesicles or at synaptic or intracellular receptors. Under these conditions, notions of receptor selectivity are moot, and it seems probable that most of the receptors identified as targets for DMT (see above) participate in producing its psychedelic effects.

Black market
Electronic cigarette cartridges filled with DMT started to be sold on the black market in 2018.

title: N,N-Dimethyltryptamine


text:
Da capo

Da capo (, , ; often abbreviated as D.C.) is an Italian musical term that means "from the beginning" (literally, "from the head"). The term is a directive to repeat the previous part of music, often used to save space, and thus is an easier way of saying to repeat the music from the beginning.

In small pieces, this might be the same thing as a repeat. But in larger works, D.C. might occur after one or more repeats of small sections, indicating a return to the very beginning. The resulting structure of the piece is generally in ternary form. Sometimes, the composer describes the part to be repeated, for example: Menuet da capo. In opera, where an aria of this structure is called a da capo aria, the repeated section is often adorned with grace notes.

The word Fine (Ital. 'end') is generally placed above the stave at the point where the movement ceases after a 'Da capo' repetition. Its place is occasionally taken by a pause (see fermata)."

Variations

 * Da Capo al Fine (often abbreviated as D.C. al Fine): Repeat from beginning to the end, or up to the word Fine (should that appear at the end of the passage)—the word Fine itself signifying the end.

 * Da Capo al Coda (often abbreviated as D.C. al Coda): Repeat from beginning to an indicated place and then play the tail part (the "Coda"). It directs the musician to go back and repeat the music from the beginning ("Capo"), and to continue playing until one reaches the first coda symbol. Upon reaching the first coda symbol, skip to the second coda symbol and continue playing until the end. The portion of the piece from the second coda to the end is often referred to as the "coda" of the piece, or quite literally as "the tail". This may also be instructed by simply using the words al Coda after which the musician is to skip to the written word Coda.
 * Da Capo al Segno (often abbreviated as D.C. al Segno): It means "From the beginning to the sign (𝄋)".

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: Da capo


text:
Dominatrix

A dominatrix ( or dominatrices ), or domme, is a woman who takes the dominant role in BDSM activities. A dominatrix can be of any sexual orientation, but this does not necessarily limit the genders of her submissive partners. Dominatrices are popularly known for inflicting physical pain on their submissive subjects, but this is not done in every case. In some instances erotic humiliation is used, such as verbal humiliation or the assignment of humiliating tasks. Dominatrices also make use of other forms of servitude. Practices of domination common to many BDSM and other various sexual relationships are also prevalent. A dominatrix is typically a paid professional (pro-domme) as the term dominatrix is little-used within the non-professional BDSM scene.

Terminology and etymology
Dominatrix is the feminine form of the Latin dominator, a ruler or lord, and was originally used in a non-sexual sense. Its use in English dates back to at least 1561. Its earliest recorded use in the prevalent modern sense, as a female dominant in sadomasochism, dates to 1961. It was initially coined to describe a woman who provides punishment-for-pay as one of the case studies within Bruce Roger's pulp paperback The Bizarre Lovemakers. The term was taken up shortly after by the Myron Kosloff title Dominatrix (with art by Eric Stanton) in 1968, and entered more popular mainstream knowledge following the 1976 film Dominatrix Without Mercy.

The term domme is likely a coined pseudo-French feminine inflection of the slang dom (short for dominant). The use of domme, dominatrix, dom, or dominant by any woman in a dominant role is chosen mostly by personal preference and the conventions of the local BDSM scene. The term mistress or dominant mistress is sometimes also used. Female dominance (also known as female domination or femdom) is a BDSM activity in which the dominant partner is female. However, while the term mistress is often used in the media, members of the BDSM community often avoid it, as it can be confused with mistress in the sense of a woman who has an illicit relationship with a married man, a term which has the negative implication of cheating on a partner. Since there is a large overlap between the BDSM and polyamory communities, where ethical conduct is a prime concern, any such relationship is a source of disapproval.

Although the term dominatrix was not used, the classic example in literature of the female dominant-male submissive relationship is portrayed in the 1870 novella Venus in Furs by Austrian writer Leopold von Sacher-Masoch. The term masochism was later derived from the author's name by Richard von Krafft-Ebing in the latter's 1886 forensic study Psychopathia Sexualis.

History

The history of the dominatrix is argued to date back to rituals of the goddess Inanna (or Ishtar as she was known in Akkadian), in ancient Mesopotamia. Ancient cuneiform texts consisting of "Hymns to Inanna" have been cited as examples of the archetype of powerful, sexual female displaying dominating behaviors and forcing gods and men into submission to her. The pseudonymous archaeologist and BDSM historian Anne O. Nomis notes that Inanna's rituals included cross-dressing of cult personnel, and rituals "imbued with pain and ecstasy, bringing about initiation and journeys of altered consciousness; punishment, moaning, ecstasy, lament and song, participants exhausting themselves with weeping and grief."

The fictional tale of Phyllis and Aristotle, which became popular and gained numerous versions from the 12th century onwards, tells the story of a dominant woman who seduced and dominated the male intellect of the greatest philosopher. In the story, Phyllis forces Aristotle to kneel on the ground so that she rides on his back while whipping and verbally humiliating him.

The profession appears to have originated as a specialization within brothels, before becoming its own unique craft. As far back as the 1590s, flagellation within an erotic setting is recorded. The profession features in erotic prints of the era, such as the British Museum mezzotint "The Cully Flaug'd" (c. 1674–1702), and in accounts of forbidden books which record the flogging schools and the activities practised.

Within the 18th century, female "Birch Disciplinarians" advertised their services in a book masked as a collection of lectures or theatrical plays, entitled "Fashionable Lectures" (c. 1761). This included the names of 57 women, some actresses and courtesans, who catered to birch discipline fantasies, keeping a room with rods and cat o' nine tails, and charging their clients a Guinea for a "lecture".

The 19th century is characterised by what Nomis characterises as the "Golden Age of the Governess". No fewer than twenty establishments were documented as having existed by the 1840s, supported entirely by flagellation practices and known as "Houses of Discipline" distinct from brothels. Amongst the well-known "dominatrix governesses" were Mrs Chalmers, Mrs Noyeau, the late Mrs Jones of Hertford Street and London Street, the late Mrs Theresa Berkley, Bessy Burgess of York Square and Mrs Pyree of Burton Crescent. The most famous of these Governess "female flagellants" was Theresa Berkley, who operated her establishment on Charlotte Street in the central London district of Marylebone. She is recorded to have used implements such as whips, canes and birches, to chastise and punish her male clients, as well as the Berkley Horse, a specially designed flogging machine, and a pulley suspension system for lifting them off the floor. Such historical use of corporal punishment and suspension, in a setting of domination roleplay, connects very closely to the practices of modern-day professional dominatrices.

The "bizarre style" (as it came to be called) of leather catsuits, claws, tail whips, and latex rubber only came about in the 20th century, initially within commercial fetish photography, and taken up by dominatrices. Within the mid-20th century, dominatrices operated in a very discreet and underground manner, which has made them difficult to trace within the historical record. A few photographs still exist of the women who ran their domination businesses in London, New York, The Hague and Hamburg's Herbertstraße, predominantly in sepia and black-and-white photographs, and scans from magazine articles, copied and re-copied. Amongst these were Miss Doreen of London who was acquainted with John Sutcliffe of AtomAge fame, whose clients reportedly included Britain's top politicians and businessmen. In New York, the dominatrix Anne Laurence was known within the underground circle of acquaintances during the 1950s, with Monique Von Cleef arriving in the early 1960s, and hitting national headlines when her home was raided by police detectives on 22 December 1965. Von Cleef went on to set up her "House of Pain" in The Hague in the 1970s, which became one of the world capitals for dominatrices, reportedly with visiting lawyers, ambassadors, diplomats and politicians. Domenica Niehoff worked as a dominatrix in Hamburg and appeared on talk shows on German television from the 1970s onwards, campaigning for sex workers' rights. Mistress Raven, founder and manager of Pandora's Box, one of New York's best known BDSM studios, was featured in Nick Broomfield's 1996 documentary film Fetishes.

Professional dominatrices

The term dominatrix is mostly used to describe a female professional dominant (or "pro-domme") who is paid to engage in BDSM play with a submissive. Professional dominatrices are not prostitutes, despite the sensual and erotic interactions they have. An appointment or roleplay is referred to as a "session", and is often conducted in a dedicated professional play space which has been set up with specialist equipment, known as a "dungeon". Sessions may also be conducted remotely by letter or telephone, or in the contemporary era of technological connectivity by email, online chat or platforms such as OnlyFans. Most, but not all, clients of female professional dominants are men. Male professional dominants also exist, catering predominantly to the gay male market.

Women who engage in female domination typically promote and title themselves under the terms "dominatrix", "mistress", "lady", "madame", "herrin" (German for "mistress") or "goddess". In a study of German dominatrices, Andrew Wilson said that the trend for dominatrices choosing names aimed at creating and maintaining an atmosphere in which class, femininity and mystery are key elements of their self-constructed identity.

Some professional dominatrices set minimum age limits for their clients. Popular requests from clients are for dungeon play including bondage, spanking and cock and ball torture, or for medical play using hoods, gas masks and urethral sounding. Verbal erotic humiliation, such as small penis humiliation, is also popular. There are some professional dominatrices that engage in sexual contact activities such as facesitting, handjobs or fellatio but others disapprove of this. Other BDSM activities can include various forms of body worship, such as foot worship, ass worship, breast worship and pussy worship; tease and denial; corporal punishment including breast torture, caning, whipping; orgasm denial; and as well as face slapping, hair pulling, dripping hot wax on the genitals, spitting, golden showers, "forced" chastity, cock and ball torture, and pussy torture.

It is not unusual for a dominatrix to consider her profession different from that of an escort and not perform tie and tease or "happy endings". Typically professional dominatrices do not have sexual intercourse with their clients, do not become naked with their clients and do not allow their clients to touch them. The Canadian dominatrix Terri-Jean Bedford, who was one of three women who initiated an application in the Ontario Superior Court seeking invalidation of Canada's laws regarding brothels, sought to differentiate for clarity her occupation as a dominatrix rather than a prostitute to the media, due to frequent misunderstanding and conflation by the public of the two terms.

That being said, it is now generally accepted that a professional dominatrix is a sex worker, and many of the acts conducted during a session may be interpreted as equally sexual to the participants.

While dominatrices come from many different backgrounds, it has been shown that a considerable number are well-educated. Research into US dominatrices published in 2012 indicated that 39% of the sample studied had received some sort of graduate training.

A 1985 study suggested that about 30 percent of participants in BDSM subculture were female. A 1994 report indicated that around a quarter of the women who took part in BDSM subculture did so professionally. In a 1995 study of Internet discussion group messages, the preference for the dominant-initiator role was expressed by 11% of messages by heterosexual women, compared to 71% of messages by heterosexual men.

Professional dominatrices can be seen advertising their services online and in print publications which carry erotic services advertising, such as contact magazines and fetish magazines that specialise in female domination. The precise number of women actively offering professional domination services is unknown. Most professional dominatrices practice in large metropolitan cities such as New York, Los Angeles, and London, with as many as 200 women working as dominatrices in Los Angeles.

Professional dominatrices may take pride or differentiation in their psychological insight into their clients' fetishes and desires, as well as their technical ability to perform complex BDSM practices, such as Japanese shibari, head-scissoring, and other forms of bondage, suspension, torture roleplay, and corporal punishment, and other such practices which require a high degree of knowledge and competency to safely oversee. From a sociological point of view, Danielle Lindemann has stated the "embattled purity regime" in which many pro-dommes emphasise their specialist knowledge and professional skills, while distancing themselves from economic criteria for success, in a way which is comparable to avant-garde artists.

Some dominatrices practice financial domination, or findom, a fetish in which a submissive is aroused by sending money or gifts to a dominatrix at her instruction. In some cases the dominatrix is given control of the submissive's finances or a "blackmail" scenario is acted out. In the majority of cases the dominatrix and the submissive do not physically meet. The interactions are typically performed using the Internet, which is also where such services are advertised. Findom was originally a niche service that a traditional dominatrix would offer, but it has become popular with less-experienced online practitioners.

To differentiate women who identify as a dominatrix but do not offer paid services, non-professional dominants are occasionally referred to as a "lifestyle" dominatrix or Mistress. The term "lifestyle" to signify BDSM is occasionally a contention topic in the BDSM community and that some dominatrices may dislike the term. Some professional dominatrices are also "lifestyle" dominatrices—i.e., in addition to paid sessions with submissive clients they engage in unpaid recreational sessions or may incorporate power exchange within their own private lives and relationships. However, the term has fallen out of general usage with respect to women who are dominant in their private relationships, and has taken on more and more the connotation of "professional". Nathalie Lugand in her 2023 book "A Psychodynamic Approach to Female Domination in BDSM Relationships" describes this strict separation as artificial.

Notable dominatrices
Catherine Robbe-Grillet is a lifestyle dominatrix. Born in Paris on September 24, 1930, she then became France's most famous lifestyle dominatrix. She is also a writer and actress, the widow of nouveau roman pioneer and sadist Alain Robbe-Grillet. She currently lives with Beverly Charpentier, a 51-year-old South African woman who is her submissive companion. Although being such a famous dominatrix, she has never accepted payment for her "ceremonies". She's quoted as saying "If someone pays, then they are in charge. I need to remain free. It is important that everyone involved knows that I do it solely for my pleasure." "Catherine is my secret garden," Charpentier says. "I have given myself to her, body and soul. She does whatever she wants, whenever she wants, with either or both, according to her pleasure—and her pleasure is also my pleasure." Robbe-Grillet has been criticised for writing about S/M stories. She identifies as a "pro-sex feminist" and "the kind of feminist who supports the right of any man or woman to work as a prostitute, if it is their free choice."

Imagery

The dominatrix is a symbolic female archetype. In popular culture, the conception of the dominatrix is generally associated with specialized clothing and props used to signify her role as a strong, dominant, sexualised woman. This role is linked to but distinct from images of sexual fetish. During the twentieth century, dominatrix imagery was developed by the work of a number of artists including the costume designer and photographer Charles Guyette, the publisher and film director Irving Klaw, and the illustrators Eric Stanton and Gene Bilbrew who drew for the fetish magazine Exotique.

One of the garments associated with the dominatrix is the catsuit. The black leather female catsuit entered dominant fetish culture in the 1950s with the AtomAge magazine and its connections to fetish fashion designer John Sutcliffe. Its appearance in mainstream culture began when catsuits were worn by strong female protagonists in popular 1960s TV programs like The Avengers and by comic super-heroines such as Catwoman. The catsuit represented the independence of a woman capable of "kick-ass" moves and action, giving complete freedom of movement. At the same time, the one-piece catsuit accentuated and exaggerated the sexualized female form, providing visual access to a woman's body, while simultaneously obstructing physical penetrative access. "You can look but you can't touch" is the message, which plays upon the BDSM practice known as "tease and denial".

Another common image is that of a dominatrix wearing thigh-high boots in leather or shiny PVC, which have long held a fetishistic status and are sometimes called kinky boots, along with very high stiletto heels. Fishnet stockings, seamed hosiery, stockings and garter belts (suspenders) are also used in the representation and attire of dominatrices, to emphasize the form and length of the legs with erotic connotation.

Tight leather corsets are another popular dominatrix garment. Gloves, whether long opera gloves or fingerless gloves, are often a further accessory to emphasize the feminine role. Neck corsets are also sometimes worn.

Dominatrices frequently wear clothing made from fetish fashion materials. Examples include PVC clothing, latex clothing and garments drawn from the leather subculture. In some cases elements of dominatrix attire, such as leather boots and peaked cap, are drawn from Nazi chic, particularly the black SS officer's uniform which has been widely adopted and fetishized by underground gay and BDSM lifestyle groups to satisfy a uniform fetish.

A dominatrix often uses strong, dominant body language which is comparable to dominant posturing in the animal world. The props she brandishes signify her role as dominatrix, such as a flogger, whip or riding crop as illustrated in the artwork of Bruno Zach in the early 20th century.

Another often-depicted characteristic of the dominatrix character is of smoking, either of tobacco cigarettes or cannabis products. While smoking tobacco has been in rapid decline worldwide, depiction of it in BDSM literature and media is increasing, as the negative image of smoking reinforces the "bad girl" stereotype associated with a dominatrix.

Practicing professional dominatrices may draw their attire from the conventional imagery associated with the role, or adapt it to create their own individual style. There is a potential conflict between meeting conventional expectations and a desire for dominant independent self-expression. Some contemporary dominatrices draw upon an eclectic range of strong female archetypes, including the goddess, the female superheroine, the femme fatale, the priestess, the empress, the queen, the governess and the KGB secret agent.

In literature
Themes associated with the dominatrix character have appeared in literature since the 10th century. Canoness Hroswitha, in her manuscript Maria, uses the word Dominatrix for the main character. She is portrayed as an unattainable woman who is too good for any of the men who are in love with her. The theme of "the unattainable woman" has been used thoroughly in medieval literature as well, although it differs from a dominatrix. Medieval themes surrounding the unattainable woman concerned issues of social classes and structure, with chivalry being a prime part of a relationship between a man and woman. There are some exceptions to this trend during medieval times. In Cervantes’ Don Quixote (1605), Celadon is imprisoned by Galatea. Celadon complains that his "mistress . . . Galatea keeps me on such a short leash". In Robert Herrick's Hesperides, a book of poems published in 1648, there were three revealing poems An Hymne to Love, The Dream, and To Love which showcase masculine longing for domination, restraint, discipline. In Ulysses by James Joyce, the character Leopold Bloom has many fantasies of submission to a lady and to receive whippings by her.

In popular culture
There have been a number of depictions of dominatrices in film and television, almost always featuring a professional dominatrix. Depictions of dominatrices in popular culture include:

 * Euphoria is a TV series in which Kat Hernandez, portrayed by Barbie Ferreira, moonlights as a dominatrix. She has to hide this part of her life from her friends and family due to societal shame.
 * Bonding is a TV series in which Tiffany "Tiff" Chester, portrayed by Zoe Levin, is a psychology student by day, and dominatrix "Mistress May" by night. Many viewers have not liked the depictions of a dominatrix in the first season, often citing it as "inaccurate". However, they hired a consultant who worked as dominatrix for 15 years to assist them in the script for the second season and fix the inaccuracies.
 * Exit to Eden is a film based on a novel of the same name with a dominatrix-based plot.

title: Dominatrix


text:
Flag of Denmark

The national flag of Denmark (Dannebrog, ) is red with a white Nordic cross, which means that the cross extends to the edges of the flag and the vertical part of the cross is shifted to the hoist side.

A banner with a white-on-red cross is attested as having been used by the kings of Denmark since the 14th century. An origin legend with considerable impact on Danish national historiography connects the introduction of the flag to the Battle of Lindanise of 1219. The elongated Nordic cross, which represents Christianity, reflects its use as a maritime flag in the 18th century. The flag became popular as a national flag in the early 16th century. Its private use was outlawed in 1834 but again permitted by a regulation of 1854. The flag holds the Guinness world record of being the oldest continuously used national flag, that is since 1625.

Description

A 1748 regulation that is still in force defines the flag as constructed of two squares of $4/4$, with a white cross $1/7$ the height of the flag and the two rectangular fields as $6/4$. Multiplying the proportions by three to get whole numbers gives the proportions in the construction sheet below (28 divided by 4 being 7 for the white cross).

Colour
No official definition of "Dannebrog rød" exists. The private company Dansk Standard, regulation number 359 (2005), defines the red colour of the flag as Pantone 186c.

1219 origin legend
A tradition recorded in the 16th century traces the origin of the flag to the campaigns of Valdemar II of Denmark (r. 1202–1241). The oldest of them is in Christiern Pedersen's "Danske Krønike", which is a sequel to Saxo's Gesta Danorum, written 1520–23. Here, the flag falls from the sky during one of Valdemar's military campaigns overseas. Pedersen also states that the very same flag was taken into exile by Eric of Pomerania in 1440.

The second source is the writing of the Franciscan friar Petrus Olai (Peder Olsen) of Roskilde (died c. 1570). This record describes a battle in 1208 near Fellin during the Estonia campaign of King Valdemar II. The Danes were all but defeated when a lamb-skin banner depicting a white cross fell from the sky and miraculously led to a Danish victory. In a third account, also by Petrus Olai, in Danmarks Tolv Herligheder ("Twelve Splendours of Denmark"), in splendour number nine, the same story is re-told almost verbatim, with a paragraph inserted correcting the year to 1219. Now, the flag is falling from the sky in the Battle of Lindanise, also known as the Battle of Valdemar (Danish: Volmerslaget), near Lindanise (Tallinn) in Estonia, of 15 June 1219.

It is this third account that has been the most influential, and some historians have treated it as the primary account taken from a (lost) source dating to the first half of the 15th century.

In Olai's account, the battle was going badly, and defeat seemed imminent. However the Danish Bishop Anders Sunesen, on top of a hill overlooking the battle, prayed to God with his arms raised, and the Danes moved closer to victory the more he prayed. When he raised his arms the Danes surged forward but when his arms grew tired and he let them fall, the Estonians turned the Danes back. Attendants rushed forward to raise his arms once again and the Danes again surged forward. But for a second time he grew so tired that he dropped his arms and the Danes again lost the advantage and were moving closer to defeat. He needed two soldiers to keep his hands up. When the Danes were about to lose, 'Dannebrog' miraculously fell from the sky and the King took it, showed it to the troops, their hearts were filled with courage, and the Danes won the battle.

The possible historical nucleus behind this origin legend was extensively discussed by Danish historians in the 19th to 20th centuries. One such example is Adolf Ditlev Jørgensen, who argued that Bishop Theoderich was the original instigator of the 1218 inquiry from Bishop Albert of Buxhoeveden to King Valdemar II which led to the Danish participation in the Baltic crusades. Jørgensen speculates that Bishop Theoderich might have carried the Knight Hospitaller's banner in the 1219 battle and that "the enemy thought this was the King's symbol and mistakenly stormed Bishop Theoderich tent. He claims that the origin of the legend of the falling flag comes from this confusion in the battle."

The Danish church-historian L. P. Fabricius (1934) ascribes the origin to the 1208 Battle of Fellin, not the Battle of Lindanise in 1219, based on the earliest source available about the story. Fabricius speculated that it might have been Archbishop Andreas Sunesøn's personal ecclesiastical banner or perhaps even the flag of Archbishop Absalon, under whose initiative and supervision several smaller crusades had already been conducted in Estonia. The banner would then already be known in Estonia. Fabricius repeats Jørgensen's idea about the flag being planted in front of Bishop Theodorik's tent, which the enemy mistakenly attacked believing it to be the tent of the King.

A different theory is briefly discussed by Fabricius and elaborated more by Helge Bruhn (1949). Bruhn interprets the story in the context of the widespread tradition of the miraculous appearance of crosses in the sky in Christian legend, specifically comparing such an event attributed to a battle of 10 September 1217 near Alcazar, where it is said that a golden cross on white appeared in the sky, to bring victory to the Christians.

In Swedish national historiography of the 18th century, there is a tale paralleling the Danish legend, in which a golden cross appears in the blue sky during a Swedish battle in Finland in 1157.

Middle Ages

The white-on-red cross emblem originates in the age of the Crusades. In the 12th century, it was also used as war flag by the Holy Roman Empire.

In the Gelre Armorial, dated c. 1340–1370, such a banner is shown alongside the coat of arms of the king of Denmark. This is the earliest known undisputed colour rendering of the Dannebrog. At about the same time, Valdemar IV of Denmark displays a cross in his coat of arms on his Danælog seal (Rettertingsseglet, dated 1356). The image from the Armorial Gelre is nearly identical to an image found in a 15th-century coat of arms book now located in the National Archives of Sweden (Riksarkivet). The seal of Eric of Pomerania (1398) as king of the Kalmar union displays the arms of Denmark's chief dexter, three lions. In this version, the lions are holding a Dannebrog banner.

The reason why the kings of Denmark in the 14th century began displaying the cross banner in their coats of arms is unknown. Caspar Paludan-Müller (1873) suggested that it may reflect a banner sent by the pope to support the Danish king during the Livonian Crusade. Adolf Ditlev Jørgensen (1875) identifies the banner as that of the Knights Hospitaller, which order had a presence in Denmark from the later 12th century.

Several coins, seals, and images exist, both foreign and domestic, from the 13th to 15th centuries and even earlier, showing heraldic designs similar to Dannebrog, alongside the royal coat of arms (three blue lions on a golden shield.)

There is a record suggesting that the Danish army had a "chief banner" (hoffuitbanner) in the early 16th century. Such a banner is mentioned in 1570 by Niels Hemmingsøn in the context of a 1520 battle between Danes and Swedes near Uppsala as nearly captured by the Swedes but saved by the heroic actions of the banner-carrier Mogens Gyldenstierne and Peder Skram. The legend attributing the miraculous origin of the flag to the campaigns of Valdemar II of Denmark (r. 1202–1241) was recorded by Christiern Pedersen and Petrus Olai in the 1520s.

Hans Svaning's History of King Hans from 1558 to 1559 and Johan Rantzau's History about the Last Dithmarschen War, from 1569, record the further fate of the Danish hoffuitbanner: According to this tradition, the original flag from the Battle of Lindanise was used in the small campaign of 1500 when King Hans tried to conquer Dithmarschen (in western Holstein in the north Germany). The flag was lost in a devastating defeat at the Battle of Hemmingstedt on 17 February 1500. In 1559, King Frederik II recaptured it during his own Dithmarschen campaign.

In 1576, the son of Johan Rantzau, Henrik Rantzau, also writes about the war and the fate of the flag, noting that the flag was in a poor condition when returned. He records that the flag after its return to Denmark was placed in the cathedral in Slesvig. Slesvig historian Ulrik Petersen (1656–1735) confirms the presence of such a banner in the cathedral in the early 17th century and records that it had crumbled away by about 1660.

Contemporary records describing the battle of Hemmingstedt make no reference to the loss of the original Dannebrog, although the capitulation state that all Danish banners lost in 1500 was to be returned. In a letter dated 22 February 1500 to Oluf Stigsøn, King John describes the battle but does not mention the loss of an important flag. In fact, the entire letter gives the impression that the lost battle was of limited importance. In 1598, Neocorus wrote that the banner captured in 1500 was brought to the church in Wöhrden and hung there for the next 59 years until it was returned to the Danes as part of the peace settlement in 1559.

Modern period

Used as a maritime flag since the 16th century, the Dannebrog was introduced as a regimental flag in the Danish army in 1785, and for the militia (landeværn) in 1801. From 1842, it was used as the flag of the entire army.

During the first half of the 19th century, in parallel to the development of Romantic nationalism in other European countries, the military flag increasingly came to be seen as representing the nation itself. Poems of this period invoking the Dannebrog were written by B.S. Ingemann, N.F.S. Grundtvig, Oehlenschläger, Chr. Winther and H.C. Andersen. By the 1830s, the military flag had become popular as an unofficial national flag, and its use by private citizens was outlawed in a circular enacted on 7 January 1834.

In the national enthusiasm sparked by the First Schleswig War during 1848–1850, the flag was still very widely displayed, and the prohibition of private use was repealed in a regulation of 7 July 1854, for the first time allowing Danish citizens to display the Dannebrog (but not the swallow-tailed Splitflag variant). Special permission to use the Splitflag was given to individual institutions and private companies, especially after 1870. In 1886, the war ministry introduced a regulation indicating that the flag should be flown from military buildings on thirteen specified days, including royal birthdays, the date of the signing of the Constitution of 5 June 1849 and on days of remembrance for military battles. In 1913, the naval ministry issued its own list of flag days. On 10 April 1915, the hoisting of any other flag on Danish soil was prohibited. This prohibition has been lifted on 24 June 2023, after a Supreme Court ruling. From 1939 until 2012, the yearbook Hvem-Hvad-Hvor included a list of flag days. As of 2019 flag days can be viewed at the "Ministry of Justice (Justitsministeriet)" as well as "The Denmark Society (Danmarks-Samfundet)".

Maritime flag and corresponding Kingdom flag

The size and shape of the civil ensign ("Koffardiflaget") for merchant ships is given in the regulation of 11 June 1748, which says: ''A red flag with a white cross with no split end. The white cross must be $1/undefined$ of the flag's height. The two first fields must be square in form and the two outer fields must be $6/4$ lengths of those''. The proportions are thus: 3:1:3 vertically and 3:1:4.5 horizontally. This definition are the absolute proportions for the Danish national flag to this day, for both the civil version of the flag ("Stutflaget"), as well as the merchant flag ("Handelsflaget"). The civil flag and the merchant flag are identical in colour and design.

A regulation passed in 1758 required Danish ships sailing in the Mediterranean to carry the royal cypher in the center of the flag in order to distinguish them from Maltese ships, due to the similarity of the flag of the Sovereign Military Order of Malta.

According to the regulation of 11 June 1748 the colour was simply red, which is common known today as "Dannebrog rød" ("Dannebrog red"). The only available red fabric dye in 1748 was made of madder root, which can be processed to produce a brilliant red dye (used historically for British soldiers' jackets). A regulation of 4 May 1927 once again states that Danish merchant ships have to fly flags according to the regulation of 1748.

The first regulation regarding the Splitflag dates from 27 March 1630, in which King Christian IV orders that Norwegian Defensionskibe (armed merchants ships) may only use the Splitflag if they are in Danish war service. In 1685 an order, distributed to a number of cities in Slesvig, states that all ships must carry the Danish flag, and in 1690 all merchant ships are forbidden to use the Splitflag, with the exception of ships sailing in the East Indies, West Indies and along the coast of Africa. In 1741 it is confirmed that the regulation of 1690 is still very much in effect; that merchant ships may not use the Splitflag. At the same time the Danish East India Company is allowed to fly the Splitflag when past the equator.

Some confusion must have existed regarding the Splitflag. In 1696 the Admiralty presented the King with a proposal for a standard regulating both size and shape of the Splitflag. In the same year a royal resolution defines the proportions of the Splitflag, which in this resolution is called Kongeflaget (the King's flag), as follows: ''The cross must be $1/undefined$ of the flags height. The two first fields must be square in form with the sides three times the cross width. The two outer fields are rectangular and $1 1/2$ the length of the square fields. The tails are the length of the flag''.

These numbers are the basic for the Splitflag, or Orlogsflag, today, though the numbers have been slightly altered. The term Orlogsflag dates from 1806 and denotes use in the Danish Navy.

From about 1750 to the early 19th century, a number of ships and companies which the government has interests in, received approval to use the Splitflag.

In the royal resolution of 25 October 1939 for the Danish Navy, it is stated that the Orlogsflag is a Splitflag with a deep red ("dybrød") or madder red ("kraprød") colour. Like the National flag, no nuance is given, but in modern days this is given as 195U. Furthermore, the size and shape is corrected in this resolution to be: "The cross must be $1/undefined$ of the flag's height. The two first fields must be square in form with the height of $3/7$ of the flag's height. The two outer fields are rectangular and $5/4$ the length of the square fields. The tails are $6/4$ the length of the rectangular fields". Thus, if compared to the standard of 1696, both the rectangular fields and the tails have decreased in size.

The Splitflag and Orlogsflag have similar shapes but different sizes and shades of red. Legally, they are two different flags. The Splitflag is a Danish flag ending in a swallow-tail, it is Dannebrog red, and is used on land. The Orlogsflag is an elongated Splitflag with a deeper red colour and is only used on sea.

The Orlogsflag with no markings, may only be used by the Royal Danish Navy. There are though a few exceptions to this. A few institutions have been allowed to fly the clean Orlogsflag. The same flag with markings has been approved for a few dozen companies and institutions over the years.

Furthermore, the Orlogsflag is only described as such if it has no additional markings. Any swallow-tail flag, no matter the colour, is called a Splitflag provided it bears additional markings.

Royal standards
The current version of the royal standard was introduced on 16 November 1972 when the Queen Margrethe II adopted a new version of her personal coat of arms. The royal standard is the flag of Denmark with a swallow-tail and charged with the monarch's coat of arms set in a white square. The centre square is 32 parts in a flag with the ratio 56:107.
 * Monarch

 * Other members of the royal family

Other flags in the Kingdom of Denmark
Greenland and the Faroe Islands are autonomous territories *
 * within the Kingdom of Denmark. They have their own official flags.
 * within the Kingdom of Denmark. They have their own official flags.
 * within the Kingdom of Denmark. They have their own official flags.

Some areas in Denmark have unofficial flags. While they have no legal recognition or regulation, they can be used freely.

The regional flags of Bornholm and Ærø are occasionally used by locals of those islands and in tourist-related businesses.

The proposal for a flag of Jutland has hardly found any actual use, maybe in part due to its peculiar design.

The flag of Vendsyssel (Vendelbrog) is seen infrequently, but many locals recognise it. According to an article in the newspaper Nordjyske, the flag had been used in the former insignia of Flight Eskadrille 723 of Aalborg Air Base, in the 1980s.

General references

 * Danmarks-Samfundet – several rules and customs about the use of Dannebrog
 * Dannebrog, Helga Bruhn, Forlaget Jespersen og Pios, Copenhagen 1949
 * Danebrog – Danmarks Palladium, E. D. Lund, Forlaget H. Hagerups, Copenhagen 1919
 * Dannebrog – Vort Flag, Lieutenant Colonel Thaulow, Forlaget Codan, Copenhagen 1943
 * DS 359:2005 'Flagdug', Dansk Standard, 2005

title: Flag of Denmark