Dimethyltryptamine

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'Dimethyltryptamine' (DMT)
Chemical name 2-(1H-indol-3-yl)-
N,N-dimethylethanamine
Chemical formula C12H16N2
Molar mass 188.27 g/mol
Density 1.099 g/ml
Melting point 49 °C and 74 °C
(two different crystal structures)
Boiling point 160 °C at 0.8 hPa
(reduced pressure)
CAS number 61-50-7
SMILES CN(C)CCC1=CNC2=C1C=CC=C2
Chemical structure of dimethyltryptamine

Dimethyltryptamine(DMT), also known as Dimitri, and N,N-dimethyltryptamine, not to be confused with 5-MeO-DMT, is a psychedelic tryptamine, similar in structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism[1] by the enzyme Tryptamine-N-methyltransferase. Pure DMT at room temperature is a light pink, orange, or yellow waxy or crystalline solid. DMT was first chemically synthesized in 1931. It also occurs naturally in many species of plants. DMT-containing plants are used in several South American shamanic practices. It is one of the main active constituents of snuffs like yopo and of the drink ayahuasca.

DMT is not orally active unless it is combined with a monoamine oxidase inhibitor (MAOI), such as harmaline. Without an MAOI, the body quickly metabolizes orally-administered DMT, and it therefore has no hallucinogenic effect. Other means of ingestion such as smoking or injecting the drug, however, can produce powerful hallucinations and entheogenic activity for a short time (usually less than half an hour).

Contents

[edit] Hallucinogenic properties

DMT is a powerful psychoactive substance. If DMT is smoked, injected, or orally ingested with an MAOI, it can produce powerful entheogenic experiences including true hallucinations (perceived extensions of reality). A trip sitter is often employed to assist the drug user in staying physically and mentally healthy, and, in the case of smoked DMT, to catch the pipe when the user loses awareness of it.

Smoked: If DMT is smoked, the maximal effects last for a short period of time (5 - 30 minutes +). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute. The relative short duration of this experience has given it the name "businessman's special," since in theory it does not take up as much of ones time as other hallucinogens like LSD.

Insufflation: If DMT is insufflated (snorted through the nostrils) it will last slightly longer than if smoked and has less powerful effects. This along with ayahuasca was the original method used by primative tribes.

Injection: Injected DMT produces an experience similar to inhalation in duration, intensity, and characteristics, although by some accounts it is more emotionally clinical (versus spiritual).

Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a decocted tea-like mixture containing DMT. There are a number of admixtures to this brew, but most commonly it is simply the leaves of Psychotria viridis (containing DMT), and the vine Banisteriopsis caapi (the MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. A common source in the western US is Reed canary grass or Phalaris arundinacea, and Harding grass or Phalaris aquatica. This invasive grass contains high levels of DMT and other alkaloids . Taken orally with an appropriate MAOI, DMT produces a long lasting (over 1 hour), slow onset experience. MAOIs should be used with extreme caution as they can have lethal complications with some prescription drugs, such as SSRI antidepressants, and some over-the-counter drugs.[2]

Induced DMT experiences can include profound time-dilation, visual and audio hallucinations, 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. [1] [2]Professor Alan Watts described the effects of DMT as "Load universe into cannon. Aim at brain. Fire."

In a 1988 study conducted at UNM, psychiatrist Rick Strassman found that approximately 20% of volunteers injected with high doses of DMT had experiences with a perceived alien entity. These beings are often termed elves. At least one subject reported sexual contact with these beings, and many others reported erotic experiences. [3]

ATC code  ?
Bioavailability  ?
Metabolism  ?
Elimination half life  ?
Excretion Urine
Pregnancy category  ?
Legal status US: I CA: III UK: 1/A
Delivery Vaporized, injected, or orally in combination with MAO inhibitors
Indicated for:
  • ?

Recreational uses:

Unethical uses:

  • ?

Other uses:
Contraindications:
  • Potentially fatal if currently taking an MAO-Inhibitor, such as many common anti-depressants
  • Do not use if suffering from Schizophrenia or similar conditions, or if such runs in your family.

[edit] Side Effects

When DMT is vaporized, the vapor produced is often felt to be very harsh on the lungs, especially if the dose contains impurities (commonly residue of sodium hydroxide or yellow/orange tannins from the plant sources), in extreme cases this can lead to retching and vomiting.

[edit] Chemistry

DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT is often synthesized by the Speeter-Anthony synthesis from indole using oxalyl chloride, dimethylamine, and lithium aluminium hydride as reagents. 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 fast and should be stored protected from air and light in a freezer.

When solvents containing N,N-DMT are evaporated different purities of alkaloid and rates of evaporation produce different crystalline patterns. Depending upon purity, the formations produced can vary from small white raised bumps which may or may not appear to have a crystalline pattern within them to a fine pointed array of delicate crystalline needled formations. Due to confinement in an evaporation container the extract shown in these photos became irregular tile-like shapes instead of the more common spoked circles at this purity. Ninety plus percent purity extract, when evaporated out of a solvent and depositing upon glass often produce small but highly defined white crystalline needles which when viewed under intense light will sparkle and upon close examination at high magnification can be seen to actually be without color and completely clear, if pure.

DMT which is in the form of a salt in dried Mimosa hostilis root bark is exceptionally free of plant fats which allows this substance to be extracted or isolated from the plant material by simply mixing powdered root bark into basified water which has had a base chemical such as NaOH dissolved into it to raise the pH of the watery mix to close to a pH of 13.5 and thereby converting the DMT salt into an alkaloid which can then be absorbed by a solvent. Once the root bark has been placed in basified water and stirred for a few minutes naphtha can be poured into the aqueous room temperature soup and stirred for twenty minutes or more which will allow the solvent to fairly selectively pull out a large portion of the alkaloid. Multiple half hour extractions are typical, stirring and extracting several times over until most of the alkaloid has been depleted through absorption into the solvent, combining the multiple fractions of solvent which have been separated from the aqueous mix each time by simply pouring the lower specific gravity solvent which is floating on top of the basified mix into a collection container and evaporated to net the alkaloid.

[edit] Speculations

Several speculative and as yet untested hypotheses suggest that endogenous DMT, produced in the human brain, is involved in certain psychological and neurological states. As DMT is naturally produced in small amounts in the brains and other tissues of humans, and other mammals[4], some believe it plays a role in promoting the visual effects of natural dreaming, near-death experiences and other mystical states. A biochemical mechanism for this was proposed by the medical researcher JC 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.[3]

Dr. Rick Strassman, while conducting DMT research in the 1990's 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 phenomenon. Only two of his test subjects reported NDE-like audio or video 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 and reptillian in nature, in technological environments[4] where the subjects were 'probed', 'tested' and sometimes even 'manipulated' by these 'beings', anyone is, regardless of interest for the subject, tempted to draw similarities between these experiences and the tales of alien encounters.

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.[5]. Unfortunately, this hypothesis does not account for the natural presence of endogenous DMT in otherwise normal humans, not to mention rats and other laboratory animals. The proposal by Dr. Callaway was the first to suggest a useful function for the endogenous production of DMT; i.e. to facilitate the visual phenomenon of normal dreaming.

Ethical concerns do not allow for the testing of this hypothesis in humans, as the biological samples must come from the living human brain. It is unknown if other animals actually do dream, as it is quite impossible to know this without their ability to tell us that they have had a dream, although REM sleep is highly correlated with dream sleep.

Writers on DMT include Terence McKenna and Jeremy Narby, though most scientists who study psychedelic drugs treat their writings with skepticism. McKenna writes of his experiences with DMT in which he encounters entities he describes as "Self-Transforming Machine Elves". 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 Rick Strassman's DMT: The Spirit Molecule (ISBN 0-89281-927-8); Strassman also proposed that DMT is made in the pineal gland, although this is only speculation.

[edit] Legal status

DMT is classified in the United States as a Schedule I drug. In December of 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 November 1st, 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.

DMT is classified in Canada as a Schedule III drug.

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

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

DMT creates legal dilemmas in many countries because possession is illegal but at the same time the drug is naturally present in the human body.

[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 Brasil:

1) Indigenous people - they are the oldest culture in the whole South America to use ayahuasca or analogue brews, such as the ones made from Jurema (Mimosa hostilis).

2) Santo Daime (Saint Giveme) and Barquinha (Lil'Boat) - the former was founded by a simple man, called Raimundo Irineu Serra, in the early 30s as an esoteric Christian religion with shamanic tendencies. The Barquinha cult was derived from this one.

3) União do Vegetal (Vegetable's Union) - another Christian ayahuasca religion, with a more Masonic tone. Today it's divided into at least three sects.

4) Neo-shamans - there are some shamanic facilitators in Brasil using ayahuasca and analogous brews in their rituals and séances, mainly in the State of Sao Paulo.

[edit] See also

[edit] Notes

  1. ^ Barker SA, Monti JA and Christian ST (1981). N,N-Dimethyltryptamine: An endogenous hallucinogen. In International Review of Neurobiology, vol 22; Academic Press, Inc.
  2. ^ Callaway JC and Grob CS (1998). Ayahuasca preparations and serotonin reuptake inhibitors: a potential combination for adverse interaction. Journal of Psychoactive Drugs 30(4): 367-369.
  3. ^ Callaway JC (1988). A proposed mechanism for the visions of dream sleep. Medical Hypotheses 26: 119-124.
  4. ^ DMT: The spirit molecul, Chapter 13, 14
  5. ^ Osmund H and Smythies JR (1952). Schizophrenia: A new approach. Journal of Mental Science 98:309-315.

[edit] References

[edit] External links

[edit] Brazilian ayahuasca churches


Psychedelic tryptamines edit

4-Acetoxy-DET, 4-Acetoxy-DIPT, 4,5-HO-MeO-DMT α-ET, α-MT, Baeocystin, Bufotenin, DET, DIPT, DMT, DPT, EIPT, Ethocin, Ethocybin, Iprocin, MET, MIPT, 5-MeO-α-ET, 5-MeO-α-MT, 5-MeO-DALT, 5-MeO-DET, 5-MeO-DIPT, 5-MeO-DMT, 5-MeO-DPT, 5-MeO-MIPT, Miprocin, Norbaeocystin, Psilocin, Psilocybin
Tryptamines - edit

4-Acetoxy-DET | 4-Acetoxy-DIPT | 4-Acetoxy-DMT | 4-HO-DIPT | 5-MeO-α-ET | 5-MeO-α-MT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-DPT | 5-MeO-MIPT | α-ET | α-MT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | Ethocybin | EIPT | Ethocin | Ibogaine | Iprocin | MET | MIPT | Miprocin | Melatonin | NMT | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan
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