Dimethyltryptamine

Categories: Psychedelic tryptamines | Neurotransmitters

Dimethyltryptamine (DMT)
Chemical name 2-(1H-indol-3-yl)-
N,N-dimethylethanamine
Chemical formula C12H16N2
Molecular 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
Image:DMT.png

Dimethyltryptamine, also known as DMT or N,N-dimethyltryptamine, is an indole, similar in structure to the neurotransmitter serotonin, created during normal metabolism in low amounts by the human body. 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 potion ayahuasca.

DMT is not orally active unless combined with a monoamine oxidase inhibitor (MAOI), such as harmaline. Without an active MAOI, the body quickly metabolizes DMT, and therefore has no significant hallucinogenic effect.

Contents

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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 (virtual experiences that are indistinguishable from reality).

Smoked: If DMT is smoked, the maximal effects last for a short period of time (30 minutes +). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute.

Insuffulation: If DMT is insuffulated (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 shamanic potion ayahuasca, or yage, is a tea-like admixture of the boiled leaves, bark or roots of a variety of plants, usually including Psychotria viridis which contains high levels of DMT, and Banisteriopsis caapi which contains harmala alkaloids which are powerful MAOIs. A common source in the western US is Reed canary grass or Phalaris arundinacea. 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, high intensity experience. MAOI should be used with extreme caution as they can make common over the counter drugs and foods toxic.

Induced DMT experiences can include profound time-dilation, time travel, journeys to paranormal realms, and encounters with spiritual beings or other mystical/trans-dimensional modalities that, by most first hand accounts, defy verbal or visual description.

In a 1988 study conducted at UNM, psychiatrist Rick Strassman found that approximately 20% of volunteers injected with high doses of DMT had experiences identical to purported Alien Abductions.


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:
  • Do not use if currently taking an MAOI
  • Do no use if suffering from Schizophrenia or similar conditions, or if such runs in your family
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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 aluminum 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 base its salts are soluble in water. DMT in solution degrades relatively fast and should be stored protected from air and light in a freezer.

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Speculations

Several highly 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 highly probably naturally produced in small amounts by the human organism, some believe it plays a role in dreaming, near-death experiences and other mystical states. It has been speculated by the researcher Jace Callaway that DMT might be connected with visual dreaming. It is also speculated that DMT can be found in elevated amounts during times of visual dreaming or after near-death experiences.

Interesting non-scientific writers on DMT include Terence McKenna and Jeremy Narby, though many people treat their writings with skepticism. McKenna writes of his experiences with DMT in which he encounters entities he describes as "Self-Transforming Machine Elves". 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.

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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 O Centro Espirita Beneficiente Uniao do Vegetal church to use hoasca tea (containg DMT) in their Christmas services this year. The Supreme Court has decided to hear the case and will likely issue a final decision in the fall of 2005.

DMT is classified in Canada as a Schedule III drug.

DMT is classified in the United Kingdom as a Schedule I/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 or, more often, mixed with Christian imagery; these were legalized recently after official inquiry into the tea.

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DMT in popular culture

The plot of the movie Blueberry touches DMT practices of Native Americans. The movie also features scenes of a DMT induced psychedelic experience.

The first letters of the Shpongle's Divine Moments of Truth track from the "Are You Shpongled?" album stand for DMT.

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External links

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Brazilian ayahuasca churches


Psychedelic tryptamines edit

5-MeO-AMT | 5-MeO-DIPT | 5-MeO-DMT | AMT | Bufotenin | DET | DIPT | DMT | DPT | Ethocin | Iprocin | Psilocin | Psilocybin


Tryptamines edit

4-Acetoxy-DET | 4-Acetoxy-DIPT | 5-MeO-AMT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-MIPT | AET | AMT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | Ethocin | Ibogaine | Iprocin | Miprocin | Melatonin | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan

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References

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