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Dimethyltryptamine

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Dimethyltryptamine
DMT
General
Systematic name 2-(1H-indol-3-yl)-N,N-dimethylethanamine
Other names  ?
Molecular formula C12H16N2
SMILES CN(C)CCC1=CNC2=C1C=CC=C2
Molar mass 188.27 g/mol
Appearance Clear to yellowish crystal
CAS number [61-50-7]
Properties
Density and phase 1.099 g/ml liquid
Solubility in water  ? g/100 ml (?°C)
Melting point 49 °C and 74 °C
(two different crystal structures)
Freezing point 160 °C at 0.8 hPa
(reduced pressure)
Acidity (pKa)  ?
Basicity (pKb)  ?
Viscosity  ? cP at ?°C
Structure
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards  ?
NFPA 704
Flash point  ?°C
R/S statement R: ?
S: ?
RTECS number  ?
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related compounds 5-MeO-DMT, DET, tryptamine
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, (not to be confused with 5-MeO-DMT), is a psychedelic. Tryptamine is 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 clear or white 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 generally not active orally 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 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).

Hallucinogenic properties Edit

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

Smoked: If DMT is smoked, the maximal effects last for a short period of time (5 - 30 minutes dose dependent). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute. The Business Man's lunch trip is a common name due to the relatively short duration of vaporized, insufflated, or injected DMT.

Insufflation: When DMT is insufflated (snorted through the nostrils) the duration is markedly increased, and some users report diminished euphoria for increased "spiritual" qualities of effect. Insufflated Yopo along with Ayahuasca were the original methods used by primitive tribes.

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

Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is practically inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and a MAOI. 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 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. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, but deep spiritual 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.[3][4]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. Some of these beings are often described as elves, or "aliens," "guides," or "helpers." Visually some are said to resemble clowns, reptiles, mantises, bees, spiders, cacti, gnomes, and stick figures. At least one subject reported sexual contact with these beings, and some others reported erotic experiences. Usually, the reported entities were experienced as the inhabitants of the mental reality the subjects reported visiting on DMT. [5]

ATC code  ?
Bioavailability  ?
Metabolism  ?
Elimination half life  ?
Excretion Urine
Pregnancy category  ?
Legal status US: I CA: III UK: 1/A
Delivery Vaporize, Injection, Insufflation, or Oral with MAOI
Indicated for:
  • ?

Recreational uses:

Unethical uses:

  • ?

Other uses:

Contraindications:
  • Do not use if suffering from Schizophrenia or similar conditions, or if such runs in your family. As with all psychoactive substances, Set & Setting are of utmost importance.

Side Effects Edit

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."[6]

Chemistry Edit

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. Highly pure DMT crystals, 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 appear colorless under high magnification.

Speculations Edit

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[1], 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. [7]

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 and reptillian in nature, in technological environments[5] where the subjects were 'probed', 'tested' and sometimes even 'manipulated' by these 'beings' (see Abduction phenomenon).

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.[8]. 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. It should be noted that DMT falls in the Tryptamine group, which also contains Serotonin, Melatonin (a hormone the Pineal Gland does indeed produce, and which contains an indole ring similar to DMT), and Psilocybin.

Legal status Edit

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 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.

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.

Culture Edit

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:

  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 São Paulo.

See also Edit

NotesEdit

  1. Barker SA, Monti JA and Christian ST (1981). N,N-Dimethyltryptamine: An endogenous hallucinogen. In International Review of Neurobiology, vol 22, pp. 83-110; 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. 2C-B, DMT, You and Me. Maps. URL accessed on 2007-01-13.
  4. DMT: Not Like any Other Experience. Miqel.com. URL accessed on 2007-01-13.
  5. 5.0 5.1 R.J. Strassman. Chapter summaries. DMT: The Spirit Molecule. URL accessed on 2007-01-13.
  6. 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.
  7. Callaway J (1988). A proposed mechanism for the visions of dream sleep. Med Hypotheses 26 (2): 119-24. PMID 3412201.
  8. Osmund H and Smythies JR (1952). Schizophrenia: A new approach. Journal of Mental Science 98:309-315.

ReferencesEdit

External linksEdit

Brazilian ayahuasca churches Edit


Tryptamines edit
4-Acetoxy-DET | 4-Acetoxy-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 | EIPT | Ethocin | Ibogaine | Iprocin | MET | MIPT | Miprocin | Melatonin | NMT | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan
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