Dimethyltryptamine

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Dimethyltryptamine
Systematic (IUPAC) name
2-(1H-indol-3-yl)-N,N-dimethyl-ethanamine
Identifiers
CAS number	61-50-7
ATC code	none
PubChem	6089
ChemSpider	5864
Chemical data
Formula	C12H16N2
Mol. mass	188.269 g/mol
SMILES	eMolecules & PubChem
Physical data
Density	1.099g/ml g/cm³
Melt. point	40–59 °C (104–138 °F)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Class A(UK) Schedule I(US)
Routes	Vaporization, Injection, Rectal, Insufflation, or Oral with MAOI

Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a naturally-occurring tryptamine and potent psychedelic drug, found not only in many plants, but also in trace amounts in the human body where its natural function is undetermined. Structurally, it is analogous to the neurotransmitter serotonin and other psychedelic tryptamines such as 5-MeO-DMT and 4-HO-DMT. DMT is created in small amounts by the human body during normal metabolism^[1] by the enzyme tryptamine-N-methyltransferase. Many cultures, indigenous and modern, ingest DMT as a psychedelic in extracted or synthesized forms.^[2] Pure DMT at room temperature is a clear or white to yellowish-red crystalline solid. A laboratory synthesis of DMT was first reported in 1931, and it was later found in many plants.^[3]

[edit] Chemistry

DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT was first extracted from the roots of Mimosa hostilis in 1946 by Brazilian ethnobotanist and chemist Gonçalves de Lima who named it Nigerine. DMT was first synthesized by a Canadian chemist Richard Manske in 1931.^[3] DMT is usually used in its base form, but it is more stable as a salt, e.g. as a fumarate. In contrast to DMT's base, its salts are water-soluble. DMT in solution degrades relatively quickly and should be stored protected from air, light, and heat in a freezer. Highly pure DMT crystals, when evaporated out of a solvent and deposited upon glass, often produce small but highly defined white crystalline needles which, when viewed under intense light, will sparkle. The crystals appear colorless under high magnification.

[edit] Pharmacology

DMT is an agonist of the 5-HT_2A receptor and also has been shown to activate the 5-HT_2C receptor^[4]. A study published in 2009 in Science shows that DMT is an agonist at the sigma-1 receptor ^[5][6] They speculated that DMT could be an endogenous ligand for this receptor. However, the concentrations of about 10 mg/l (50 µM) that is needed for sigma-1 activation is many orders of magnitude higher than physiologically observed concentrations and is also about two orders of magnitude higher than that needed to activate the 5-HT_2A receptor. Although this factor is only relevant if endogenous DMT acts as a hormone. The pharmacology of DMT is more suggestive of that of a neurotransmitter rather than a hormone^[7]. As a transmitter DMT is able to have localized effects as the concentrations at the site of release are many times higher than the resulting plasma levels. DMT has also been shown to have efficacy at the trace amine associated receptor TAAR1.^{[citation needed]} TAARs have also been proposed as the natural receptor of endogenous DMT.^[8]

[edit] Psychedelic properties

DMT occurs naturally in many species of plants often in conjunction with its close chemical relatives 5-MeO-DMT and bufotenin (5-OH-DMT).^[9] DMT-containing plants are commonly used in several South American shamanic practices. It is usually one of the main active constituents of the drink ayahuasca^[2], however ayahuasca is sometimes brewed without plants that produce DMT. DMT occurs as the primary active alkaloid in several plants including such plants as Mimosa hostilis, 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.^[9] DMT is also found as a minor alkaloid in the beans of Anadenanthera peregrina and Anadenanthera colubrina used to make Yopo and Vilca snuff in which bufotenin is the main active alkaloid.^[9][10] Psilocybin, the active chemical in psilocybin mushrooms can also be considered a close chemical relative^[11] for the psilocybin molecule contains a DMT molecule at the end as with other close chemical relatives (4-Phosphoryloxy-N,N-dimethyl-tryptamine).

The psychotropic effects of DMT were first studied scientifically by the Hungarian chemist and psychologist Dr. Stephen Szára, who performed research with volunteers in the mid-1950s. Szára, who later worked for the US 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.^[12]

DMT during various stages of purification in an illegal drug laboratory in Los Angeles

DMT is generally not active orally unless it is combined with a monoamine oxidase inhibitor (MAOI) such as a reversible inhibitor of monoamine oxidase A (RIMA), e.g., harmaline. Without a MAOI, the body quickly metabolizes orally administered DMT, and it therefore has no hallucinogenic effect unless the dose exceeds monoamine oxidase's metabolic capacity (very rare). Other means of ingestion such as smoking or injecting the drug can produce powerful hallucinations and entheogenic activity for a short time (usually less than half an hour), as the DMT reaches the brain before it can be metabolised by the body's natural monoamine oxidase. Taking a MAOI prior to smoking or injecting DMT will greatly prolong and potentiate the effects of DMT. If DMT is smoked, injected, or orally ingested with a MAOI, it can produce powerful entheogenic experiences including intense visuals, euphoria, even true hallucinations (perceived extensions of reality).^[13]

Inhaled: If DMT is smoked, the effects last for a short period of time, usually 5 to 30 minutes (dependent on dose). The onset after inhalation is very fast (less than 45 seconds) and peak effects are reached within a minute. In the 1960s, some reportedly referred to DMT as "the businessman's trip"^[14] due to the relatively short duration of vaporized, insufflated, or injected DMT. Although the smoke produced is described as harsh by some, it can be mixed with cannabis or one of many smoking mixtures and be used in a pipe, a waterpipe (popularly known as a bong), or a vaporizer. This helps to improve the smoothness of the smoke, ultimately making the substance easier to ingest.

Insufflation: When DMT is insufflated, the duration is markedly increased, and some users report diminished euphoria but an intensified otherworldly experience.

Injection: Injected DMT produces an experience that is similar to inhalation in duration, intensity, and characteristics.

Oral ingestion: DMT is broken down by the digestive enzyme monoamine oxidase and is practically inactive if taken orally, unless combined with a MAOI. The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and an MAOI.^[2] There are a variety of recipes to this brew, but most commonly it is simply the leaves of Psychotria viridis (the source of DMT) and the vine Banisteriopsis caapi (the source of MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. Two common sources 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. In addition, Jurema (Mimosa hostilis) shows evidence of DMT content: the pink layer in the bark of this vine contains a high concentration of N,N-DMT. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, deep metaphysical experience similar to that of psilocybin mushrooms, but more intense with a shorter duration.^[2] MAOIs should be used with extreme caution as they can have lethal complications with some prescription drugs such as SSRI antidepressants, some over-the-counter drugs,^[15] and many common foods.

Induced DMT experiences can include profound time-dilation, visual and auditory illusions, and other experiences that, by most firsthand accounts, defy verbal or visual description. Some users report intense erotic imagery and sensations and utilize the drug in a ritual sexual context.^[2][16][17]

In a study conducted from 1990 through 1995, University of New Mexico psychiatrist Rick Strassman found that many volunteers injected with high doses of DMT had experiences with a perceived alien entity. Usually, the reported entities were experienced as the inhabitants of a perceived independent reality the subjects reported visiting while under the influence of DMT.^[12]

[edit] Side effects

When DMT is vaporized, the vapor produced is often felt to be very harsh on the lungs.

According to a "Dose-response study of N,N-dimethyltryptamine in humans" by Rick Strassman, "Dimethyltryptamine dose dependently 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 rose equally in response to all doses of DMT, and melatonin levels were unaffected."^[18]

[edit] Speculations

DMT crystal at 400x magnification.

Several speculative and yet untested hypotheses suggest that endogenous DMT, produced in the human brain, is involved in certain psychological and neurological states. DMT is naturally produced in small amounts in the brain and other tissues of humans and other mammals.^[19] Some believe it plays a role in mediating the visual effects of natural dreaming, and also near-death experiences, religious visions and other mystical states.^[20] A biochemical mechanism for this was proposed by the medical researcher J. C. Callaway, who suggested in 1988 that DMT might be connected with visual dream phenomena, where brain DMT levels are periodically elevated to induce visual dreaming and possibly other natural states of mind.^[21] A new theory proposed is that in addition to being involved in altered states of consciousness, endogenous DMT may be involved in the creation of normal waking states of consciousness. It is proposed that DMT and other endogenous hallucinogens mediate their neurological abilities by acting as neurotransmitters at a sub class of the trace amine receptors; a group of receptors found in the CNS where DMT and other hallucinogens have been shown to have activity. Wallach further proposes that in this way waking consciousness can be thought of as a controlled psychedelic experience. It is when the control of these systems becomes loosened and their behavior no longer correlates with the external world that the altered states arise. ^[22]

Dr. Rick Strassman, while conducting DMT research in the 1990s at the University of New Mexico, advanced the theory that a massive release of DMT from the pineal gland prior to death or near death was the cause of the near death experience (NDE) phenomenon. Several of his test subjects reported NDE-like audio or visual hallucinations. His explanation for this was the possible lack of panic involved in the clinical setting and possible dosage differences between those administered and those encountered in actual NDE cases.

Several subjects also reported contact with 'other beings', alien like, insectoid or reptilian in nature, in highly advanced technological environments^[12] where the subjects were 'carried', 'probed', 'tested', 'manipulated', 'dismembered', 'taught', 'loved' and even 'raped' by these 'beings'. Those could be the same beings that some of the ancient cultures that consumed DMT rich beverages, like ayahuasca, considered their gods. Also, this leads to the idea that the alien abduction phenomenon could be produced by high levels of endogenous DMT in the human body, and that it might be a physiological condition that could pass genetically to the descendants of such people. (see Abduction phenomenon). Strassman noted, though, that the experience might be highly influenced by the actual user's life, showing what the person needs, given their personal story of the moment, more than what is wanted, and also that the setting could play a partial role, too (ex: in a waking dream state).

In the 1950s, the endogenous production of psychoactive agents was considered to be a potential explanation for the hallucinatory symptoms of some psychiatric diseases as the transmethylation hypothesis^[23] (see also adrenochrome). Unfortunately, this hypothesis does not account for the natural presence of endogenous DMT in otherwise normal humans, rats and other laboratory animals. The proposal by Dr. Callaway was, however, the first to suggest a useful function for the endogenous production of DMT: to facilitate the visual phenomenon of normal dreaming.

Writers on DMT include Terence McKenna, Jeremy Narby and Graham Hancock (in passages of Supernatural) though most scientists who study psychedelic drugs treat their writings with skepticism^{[citation needed]}. McKenna writes of his DMT experiences with a decidedly less skeptical slant, often presuming that the drug's "intoxication" is indicative of realms of consciousness equally as valid as waking-life if not more so. In his writings and speeches, he recounts encounters with entities he sometimes describes as "Self-Transforming Machine Elves" among equally colorful phrases. McKenna believed DMT to be a tool that could be used to enhance communication and allow for communication with other-worldly entities. Other users report visitation from external intelligences attempting to impart information. These Machine Elf experiences are said to be shared by many DMT users. From a researcher's perspective, perhaps best known is Dr. Rick Strassman's DMT: The Spirit Molecule (ISBN 0-89281-927-8);^[24] Dr. Strassman speculated that DMT is made in the pineal gland, largely because the necessary constituents (see methyltransferases) needed to make DMT are found in the pineal gland.

[edit] Legal status

[edit] 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 Espirita Beneficente Uniao do Vegetal, the Supreme Court heard arguments on November 1, 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.

[edit] Canada

DMT is classified in Canada as a Schedule III drug.

[edit] France

DMT, along with most of its plant sources, is classified in France as a stupéfiant (Narcotic).

[edit] United Kingdom

DMT is classified in the United Kingdom as a Class A drug.

[edit] New Zealand

DMT is classified as a Class A drug in New Zealand.

[edit] Culture

In Brazil there are a number of religious movements based on the use of ayahuasca, usually in an animistic context that may be shamanistic, sometimes mixed with Christian imagery. There are four main branches using DMT-MAOI based sacraments in Brazil:

• Indigenous Brazilian. These are the oldest cultures in the whole of South America that continue to use ayahuasca or analogue brews, such as the ones made from Jurema in the Pernambuco, near Recife.
• Santo Daime ("Saint Give Unto Me") and Barquinha ("Little Boat"). A syncretic religion from Brazil. The former was founded by Raimundo Irineu Serra in the early 1930s, as an esoteric Christian religion with shamanic tendencies. The Barquinha was derived from this one.
• União do Vegetal (Union of Vegetal or UDV). Another Christian ayahuasca religion from Brazil, is a single unified organization with a democratic structure.
• Neo-shamans. There are some self-styled shamanic facilitators in Brazil and other South American countries that use ayahuasca or analogous brews in their rituals and séances.

[edit] See also

• Ayahuasca
• Bufotenin
• Machine elf
• Terence McKenna
• Rick Strassman

[edit] References

[edit] External links

• Erowid DMT Vault
• DMT chapter from TiHKAL
• An overview of DMT: The Spirit Molecule by its author, Rick Strassman
• The Spirit Molecule - a documentary film about DMT