Dimethyltryptamine

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Dimethyltryptamine
200px
200px
Systematic (IUPAC) name
2-(1H-indol-3-yl)-N,N-dimethylethanamine
Clinical data
Routes of
administration		 Oral (with an MAOI), Insufflated, Rectal, Smoked (or vaporized), IM, IV
Legal status
Legal status
Identifiers
CAS Number 61-50-7
ATC code none
PubChem CID 6089
IUPHAR/BPS 141
ChemSpider 5864
Chemical data
Formula C12H16N2
Molar mass 188.269 g/mol[[Script error: No such module "String".]]
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Physical data
Density 1.099g/ml g/cm3
Melting point 40 to 59 °C (104 to 138 °F)
Boiling point 160 °C (320 °F) @ 0.6 Torr[1] also reported as 80 - 135 °C @ 0.03 Torr[2]
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N,N-Dimethyltryptamine (DMT) is a naturally occurring hallucinogenic drug of the tryptamine family. This drug is found not only in many plants,[3] but also in trace amounts in the human body, where its natural function remains undetermined. Structurally, it is analogous to the neurotransmitter serotonin (5-HT) and other hallucinogenic tryptamines such as 5-MeO-DMT, bufotenin (5-OH-DMT), and psilocin (4-HO-DMT). DMT is created in small amounts by the human body during normal metabolism[4] by the enzyme tryptamine-N-methyltransferase. Many cultures, indigenous and modern, ingest DMT as a psychedelic, in either extracted or synthesized forms.[5] When refined, DMT is a clear to white, crystalline solid. However, DMT found on the illicit market is commonly impure and may appear yellow, orange, or salmon in color, unless special care has been taken to remove these impurities. Such impurities result from degradation or originate from plant matter from which the DMT may have been extracted.

Biosynthesis

Biosynthetic pathway for N-N,dimethyltryptamine

Dimethyltryptamine is an indole-alkaloid derived from the shikimate pathway. Its biosynthesis is relatively simple and summarized in the picture to the left. In plants, the tryptophan is produced endogenously where in animals the tryptophan used comes from diet. No matter the source of tryptophan, the biosynthesis begins with the decarboxylation of L-tryptophan (step 1). Once decarboxylated, tryptamine (step 2) is dimethylated by S-adenosyl-methionine (SAM) via nucleophilic attack. This reaction is mediated by tryptamine-N-methyltransferase enzyme. This produces the product (step 3). The mechanism has been proven by radio labelling of SAM with carbon-14.[6] The study found that various mammal tissues contained enzymes capable of performing the above transformation.

Chemistry

File:D-Tryp.jpg
DMT Crystals

DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT was first synthesized by Canadian chemist Richard Manske in 1931.[3] Natural DMT was first extracted from the plant roots of Mimosa hostilis in 1946 by Brazilian ethnobotanist and chemist Gonçalves de Lima who named it Nigerine. DMT is commonly handled and stored as a fumarate as other DMT acid salts are generally very hygroscopic and will not readily crystallize. Its freebase form, although less stable than DMT fumarate, is favored by recreational users choosing to vaporize (smoke) the chemical because it has a lower boiling point. 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.

Pharmacology

DMT acts as a non-selective agonist at most or all of the serotonin receptors (including 5-HT2A and 5-HT2C),[7][8][9][10] and has also been shown to possess affinity for the D1, α1-adrenergic, α2-adrenergic, imidazoline-1, sigma-1, and trace amine-associated receptors.[7][8][11] At the trace amine-associated receptor (TAAR) and the sigma-1 receptor it acts as an agonist,[11][12] whereas its efficacies at the other sites are unclear. It has also been shown to bind to the SERT and VMAT2 as a substrate (instead of inhibitor), and may act as a serotonin releasing agent.[13] The psychedelic effects of DMT can likely largely be attributed to activation of the 5-HT2A receptor,[14][15] though it cannot be ruled out whether other receptors such as 5-HT2C, sigma-1, and TAAR may also play a role.[11][12][15]

It was speculated that DMT could be an endogenous ligand for the sigma-1 receptor. In this report, the concentration of DMT needed for sigma-1 activation is about 9.4 mg/L (50 µM). This concentration is higher than the average concentration measured in brain tissue or plasma, and is also about two orders of magnitude higher than that needed to activate the 5-HT2A receptor in vitro. In humans, effective hallucinogenic doses produce peak DMT plasma concentrations ranging between 12 and 90 µg/L and with an apparent volume of distribution of 36 to 55 L.[16][17][18]

The corresponding average molar plasma concentration of DMT is therefore in the range of 0.060–0.500 µM. However, the relatively high volume of distribution of DMT indicates significant movement of the drug from plasma into tissues and several reports have described the active accumulation of DMT and other tryptamines into rat brain following peripheral administration.[19][20][21][22][23] Similar active uptake processes in human brain may plausibly concentrate DMT within neurons by several-fold or more, resulting in local concentrations in the micromolar or higher range. Interestingly, the concentrations of DMT required to occupy a significant fraction of any of its known receptor binding sites are between 1,000 and 1,000,000-fold lower than the calculated synaptic concentration of other neurotransmitters. For example, using amperometric measurements, the synaptic concentration of dopamine was estimated to reach about 75 mM.[24] DMT also activated the trace amine associated receptor TAAR1, at the tested high concentration.[25]

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).[26] DMT-containing plants are commonly used in South American Shamanic practices. It is usually one of the main active constituents of the drink ayahuasca,[5] however ayahuasca is sometimes brewed without plants that produce DMT. It occurs as the primary psychoactive alkaloid in several plants including 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.[26] 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.[26][27] Psilocybin and psilocin, active chemicals in many psychedelic mushrooms, are structurally very similar to DMT.[28]

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.[29]

File:Dmtlab.jpg
DMT during various stages of purification in an illegal drug laboratory in Los Angeles

DMT can produce powerful entheogenic experiences including intense visuals, euphoria, even true hallucinations (perceived extensions of reality). 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. Uninhibited, the human body metabolizes DMT too rapidly for oral administration to be effective. 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 metabolized by the body's natural monoamine oxidase. Taking a MAOI prior to smoking or injecting DMT prolongs and potentiates the effects.[30]

Inhalation

A standard dose for smoked DMT is between 15–60 mg. This is generally smoked in a few successive breaths. 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, some reportedly referred to DMT as "the businessman's trip"[31] because of the relatively short duration of vaporized, insufflated, or injected DMT. DMT is commonly vaporized in glass pipes such as those used with crack cocaine and methamphetamine. Improvised smoking devices can be constructed from light bulbs. The vapor is sometimes described as harsh, and some users even compare its flavor to that of burning plastic. Some users elect to combine it with cannabis, parsley, mullein, or other plants in an attempt to improve flavor and reduce harshness. Combining DMT with plant matter or depositing it upon a substrate of ash also facilitates use of an ordinary pipe, a bong, or a vaporizer.

Insufflation

Insufflating DMT (commonly as a freebase or fumarate) requires a higher dose than does inhalation. The duration is markedly increased, and some users report diminished euphoria but an intensified otherworldly experience[citation needed].

Injection

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

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 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.[29] In a September, 2009, interview with Examiner.com, Strassman described the effects on participants in the study: "Subjectively, the most interesting results were that high doses of DMT seemed to allow the consciousness of our volunteers to enter into non-corporeal, free-standing, independent realms of existence inhabited by beings of light who oftentimes were expecting the “volunteers,” and with whom the volunteers interacted. While “typical” near-death and mystical states occurred, they were relatively rare."

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 a MAOI.[5] 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). It has often puzzled researchers how the natives managed to find this combination without modern analytical chemistry[citation needed]. 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.[5] 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,[32] and many common foods.[33]

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.[5][34][35]

Distinguish from 5-MeO-DMT

5-MeO-DMT, a psychedelic drug structurally similar to N,N-DMT, is sometimes referred to as DMT through ignorance or by abbreviation. As a white, crystalline solid, it is also similar in appearance to DMT. However, it is considerably more potent (5-MeO-DMT typical smoked dose: 5–20 mg), and care should be taken to clearly differentiate between the two drugs to avoid accidental overdose.[36]

Side effects

When DMT is vaporized, the inhaled vapor feels harsh to a minority of users. According to a "Dose-response study of N,N-dimethyltryptamine in humans" by Rick Strassman, "Dimethyltryptamine dose 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 rose equally in response to all doses of DMT, and melatonin levels were unaffected."[37]

Speculation

File:Dmtx400tt9.jpg
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.[38] It may play a role in mediating the visual effects of natural dreaming, and also near-death experiences, religious visions and other mystical states.[39] 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.[40] A new hypothesis 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.[41]

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[29] where the subjects were 'carried', 'probed', 'tested', 'manipulated', 'dismembered', 'taught', 'loved' and even 'raped' by these 'beings' (one could note the strong similarities of these bodily tests/invasions in other psychedelic experiences throughout time, outlined in Graham Hancock's "Supernatural"[42]). Strassman has 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 in substantially greater concentrations than any other part of the body. However, there is no scientific proof of this.

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[43] (see also adrenochrome), though this hypothesis does not account for the natural presence of endogenous DMT in otherwise normal humans, rats and other laboratory animals.

Writers on DMT include Terence McKenna, Jeremy Narby and Graham Hancock. In his writings and speeches, Terence McKenna recounts encounters with entities he sometimes describes as "Self-Transforming Machine Elves" among other 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 only a minority of DMT users and some people report never seeing or experiencing anything of that nature.

Legal status

International Law

DMT is classified as a Schedule I drug under the UN 1971 Convention on Psychotropic Substances, meaning that use of DMT is supposed to be restricted to scientific research and medical use and international trade in DMT is supposed to be closely monitored. Natural materials containing DMT, including ayahuasca, are explicitly not regulated under the 1971 Psychotropic Convention.[44]

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.

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,[45] presided over by Judge Owen M. Panner, was ruled in favor of the Santo Daime church. As of March 21, 2009 a federal judge says members of the church in Ashland can import, distribute and brew ayahuasca. U.S. District Judge Owen 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 and prosecuting church members who follow a list of regulations set out in his order.[46][47]

Canada

DMT is classified in Canada as a Schedule III drug.

France

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

United Kingdom

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

New Zealand

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

Culture

In South America there are a number of indigenous traditions and more recent religious movements based on the use of ayahuasca, usually in an animistic context that may be mixed with Christian imagery. There are four main branches using DMT-MAOI based sacraments in South America:

  • Amazonian Peoples. There are many indigenous cultures in South America, mostly in the Upper Amazon Basin whose traditional religious practices include the use of ayahuasca. 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 or Iquitos in Peru.
  • 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.

See also

          

   

References

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External links

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  18. Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  19. Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  20. Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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  23. Jump up ↑ Yanai K, Ido T, Ishiwata K; et al. (1986). "In vivo kinetics and displacement study of a carbon-11-labeled hallucinogen, N,N-[11C]dimethyltryptamine". Eur J Nucl Med. 12 (3): 141–6. doi:10.1007/BF00276707. PMID 3489620. 
  24. Jump up ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  25. Jump up ↑ Bunzow JR, Sonders MS, Arttamangkul S (2001). "Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor". Mol. Pharmacol. 60 (6): 1181–8. PMID 11723224. 
  26. ↑ Jump up to: 26.0 26.1 26.2 Anadenanthera: Visionary Plant Of Ancient South America By Constantino Manuel Torres, David B. Repke, 2006, ISBN 0789026422
  27. Jump up ↑ Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine by Jonathan Ott, The Journal of Psychoactive Drugs, September 2001
  28. Jump up ↑ Relation between DMT and other related compounds http://deoxy.org/t_thc.htm
  29. ↑ Jump up to: 29.0 29.1 29.2 R.J. Strassman. "Chapter summaries". DMT: The Spirit Molecule. Retrieved 2007-01-13. 
  30. Jump up ↑ http://www.erowid.org/chemicals/dmt/dmt.shtml
  31. Jump up ↑ Haroz, R; Greenberg, M (2005). "Emerging Drugs of Abuse". Medical Clinics of North America. 89 (6): 1259. doi:10.1016/j.mcna.2005.06.008. PMID 16227062. 
  32. Jump up ↑ Callaway J.C. and Grob C.S. (1998). Ayahuasca preparations and serotonin reuptake inhibitors: a potential combination for adverse interaction. Journal of Psychoactive Drugs 30(4): 367-369.
  33. Jump up ↑ "MAOIs and Diet". http://www.mayoclinic.com. Retrieved 2009-02-22.  External link in |publisher= (help)
  34. Jump up ↑ "2C-B, DMT, You and Me". Maps. Retrieved 2007-01-13. 
  35. Jump up ↑ "Entheogens & Visionary Medicine Pages". Miqel.com. Retrieved 2007-08-17. 
  36. Jump up ↑ http://www.erowid.org/chemicals/5meo_dmt/5meo_dmt_dose.shtml
  37. Jump up ↑ R.J. Strassman and C.R. Qualls (February 1994). "Dose-response study of N,N-dimethyltryptamine in humans". Arch Gen Psychiatry. 51 (2): 85–97. PMID 8297216. 
  38. Jump up ↑ "Erowid DMT Vault: Journal Articles & Abstracts". Retrieved 2007-09-05. 
  39. Jump up ↑ http://www.npr.org/templates/story/story.php?storyId=104240746&sc=fb&cc=fp
  40. Jump up ↑ Callaway J (1988). "A proposed mechanism for the visions of dream sleep". Med Hypotheses. 26 (2): 119–24. doi:10.1016/0306-9877(88)90064-3. PMID 3412201. 
  41. Jump up ↑ Wallach J (2008). "Endogenous hallucinogens as ligands of the trace amine receptors: A possible role in sensory perception". Med Hypotheses. in print (in print): in print. doi:10.1016/j.mehy.2008.07.052. PMID 18805646. 
  42. Jump up ↑ http://www.amazon.com/Supernatural-Meetings-Ancient-Teachers-Mankind/dp/1932857400
  43. Jump up ↑ Osmund H and Smythies JR (1952). Schizophrenia: A new approach. Journal of Mental Science 98:309-315.
  44. Jump up ↑ Erowid
  45. Jump up ↑ Church of the Holy Light of the Queen v. Mukasey
  46. Jump up ↑ Pharma-Law E-News
  47. Jump up ↑ Portland Tribune
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