Dimethyltryptamine

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

Dimethyltryptamine, also known as DMT and N,N-dimethyltryptamine, not to be confused with 5-MeO-DMT, a psychedelic tryptamine, similar in structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism. Pure DMT at room temperature is a colorless 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 DMT, and it therefore has no hallucinogenic effect.

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.

Insufflation: If DMT is insufflated (snorted through the nostrils) it will last slightly longer than if smoked and has less powerful effects.

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.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.

Induced DMT experiences can include profound time-dilation, visual and audio hallucinations, and other experiences that, by most first hand accounts, defy verbal or visual description. 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.

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

Recreational uses:

Unethical uses:

Other uses:

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.

Indicated for:

Contraindications:

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.

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^*, 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.Callaway JC (1988). A proposed mechanism for the visions of dream sleep. Medical Hypotheses 26: 119-124.

In the 1950s, the endogenous production of psychoactive agents was considered to be a potential explanation for the hallucinatory symptoms of some psyciatric diseases as the transmethylation hypothesis.Osmund H and Smythies JR (1952). Schizophrenia: A new approach. Journal of Mental Science 98:309-315.. 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 brian. 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 for communication. 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 0892819278); Strassman also proposed that DMT is made in the pineal gland, although this is only speculation.

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.

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.

External links

Brazilian ayahuasca churches

Santo Daime (in English)
União do Vegetal (in English)
BBC News story: US church's illegal tea faces ban

References

Books

(discusses DMT and implications for our understanding of reality)

Psychedelic tryptamines | Alkaloids

Gourt Home::Gourt :: Dimethyltryptamine