DMT pharmacology

Excerpt from a pharmacology textbook published in 1988

This is the prototype member of the tryptamine subclass of indole derivatives. The structural formula is:

DMT

The drug is a constituent of many of the same South American snuffs and drinks that contain other psychedelic indole deriviatives, it is often found in the same plants as 5-MeO-DMT, and Indians add a substance containing it to drinks containing harmala alkaloids. DMT is the major constituent of the bark of Virola calophylla; it is also found in the seeds of Anadenanthera peregina; in the seeds of the vine Mimosa hostilis, used in eastern Brazil to make a drink called "ajuca" or "jurema"; in the leaves of Banisteriopsis rusbyana, which are added to the harmaline drinks derived from other plants of the Banisteriopsis genus to make "oco-yage"; and in the leaves of Psychotria viridis, also added to the Banisteriopsis drinks. Like 5-MeO-DMT, DMT must be combined with monoamine oxidase inhibitors to become active orally.

Dose

First strong effects are felt at about 50mg, whether it is smoked or injected. Tolerance develops only after extremely frequent use - injections every two hours for three weeks in rats; at that dose frequency, but not otherwise, there is also a cross-tolerance between DMT and LSD (Rosenberg et al [1964]; Kovacic & Domino [1976]).

Physiological effects

Resembles LSD, but sympathomimetic symptoms like dilated pupils, heightened blood pressure, and increased pulse rate are more common and more intense.

Psychological Effects

Like LSD but often more intense. Since it is not taken by mouth, the effects come on suddenly and can be overwhelming. The term "mind blowing" might have been invented for this drug. The experience was described by Alan Watts as like "being fired out of the nozzle of an atomic cannon" (Leary [1968a] p.215). Thoughts and visions crowd in at great speed; a sense of leaving or transcending time and a feeling that objects have lost all form and dissolved into a play of vibrations are characteristic. The effect can be like instant transportation to another universe for a timeless sojourn.

Duration of action

When DMT is smoked or injected, effects begin in seconds, reach a peak in five to twenty minutes and end after a half hour or so. This has earned it the name "businessman's trip." The brevity of the experience make its intensity bearable, and, for some, desirable.

At least two synthetic drugs in which the methyl group of DMT is replaced by a higher radical are psychedelic:

DETDPT

The drug DET is active at the same dose as DMT and the effects last slightly longer, about one and a half to two hours. DPT is longer-acting still and has fewer autonomic side effects. In therapeutic experiments its action continues for one and a half to two hours at the lowest effective dose, 15 to 30mg, and for four to six hours at doses in the range of 60 to 150mg. Both DET and DPT are milder than DMT. The drug 6-FDET (6-fluorodiethyltryptamine) resembles DET in its effects. All these drugs, like DMT, are inactive orally and must be smoked or injected. Dibutyltryptamine (DBT) and higher substitutions are inert, but other synthetic drugs related to DMT may be psychoactive.

Description and properties

Text from a January 1977 journal article by Alexander T. Shulgin

DMT, N,N-diemethyltryptamine, Nigerine, desoxybufotenine, 3-(2-dimethylaminoethyl)-indole is a white, pungent-smelling, crystalline solid with a melting point of 49-50 degrees Celsius, hydrochloride salt hygroscopic, picrate m.p. 171-172 degrees Celsius and methiodide m.p. 215-216 degrees Celsius. It is insoluble in water, but soluble in organic solvents and aqueous acids.

History

DMT was first synthesized in 1931, and demonstrated to be hallucinogenic in 1956. It has been shown to be present in many plant genera: Acacia, Anandenanthera, Mimosa, Piptadenia, Virola) and is a major component of several hallucinogenic snuffs (cohoba, parica, yopo). It is also present in the intoxicating beverage ayahuasca made from Banisteriopsis caapi, and it may have oral effectiveness due to the presence of several naturally occuring inhibitors of catabolic deamination.

Human Biochemistry and Pharmacology

Both the parent compound tryptamine and the N-methyltransferase system which is capable of converting it to DMT occur in humans, but there is as yet no evidence that DMT is formed "in vivo". DMT has nonetheless been identified in trace amounts in the blood and urine of both normals and of schizophrenic patients, but its origins and functions are unknown. Following intramuscular administration, maximum blood levels of about 100ng/ml are observed in 10 minutes, coincident with the maximum changes in electroencephalographic responses. The plasma clearance t-1/2 [half-life] is about 15 minutes. Elevated blood levels of indoleacetic acid (IAA) are seen during the time of peak effects, implying its role as a metabolite. Urine levels of IAA are also elevated and account for about 30% of the administered drug. An increase in 5-hydroxy-IAA excretion suggests the involvement of serotonin in DMT action. Unchanged DMT is not excreted.

Human psychopharmacology

DMT is inactive orally at dosages of over 1000mg. With intramuscular injection, there is an abrupt threshold of activity shown with 30mg, and a complete psychedelic experience results from the administration of 50-70mg (75mg subcutaneously, 30mg by inhalation). An unusual feature of the induced intoxication is the speed of onset and short duration. Within 5 minutes of administration there is mydriasis [dilated pupils], tachycardia [rapid heart beat], a measurable increase in blood pressure, and related vegetative disturbances which usually persist througout the drug experience. In 10-15 minutes, the full intoxication is realized, generally characterized by hallucinations with the eyes either open or closed, and extensive movement within the visual field. There is difficulty in the expression of one's thoughts, and in concentration on a given subject. There is usually a mood change to the euphoric with unmotivated laughter, but instances have been reported in which paranoid ideation has promoted anxieties and feelings of forboding into a state of panic. The subject is largely symptom-free at 60 minutes, although some residual effects have been seen in the second hour. With the inhalation route of administration the time scale is contracted, with onset of effects noted in 10 seconds, a short period of full intoxication at 2-3 minutes, and a complete freedom from any residual effects within 10 minutes. At higher drug levels, there are increased vegetative symptoms, and these effectively overwhelm the psychedelic experience at dosages of 150mg i.m. Interactions with other drugs are rarely seen; a sensitivity has been observed with pretreatment with methlysergide, but there is no cross-tolerance with LSD. Repeated usage does not appear to lead to either physical or psychological dependency.

Legal Status

DMT is explicitly named as a Schedule I drug in the Federal Controlled Substances Act; registry number 7435 (United States of America). In the UK, DMT is classified as a Class A drug.

Pharmacotheon DMT Entry

DIMETHYLTRYPTAMINE [Merck Index 11:3251]

Synonyms
3-[2-(dimethylamino)ethyl]-indole;N,N-dimethyltryptamine; DMT; nigerine
Physical
C14H20N2O; molecular weight 232.45;
C 72.34% H 8.67% N 12.10% O 6.88%
Isolation
Fish, J.Am. Chem. Soc.77:5892,1955 (Anadenanthera peregrina);
Agurell, Acta Chem. Scand. 23: 903, 1969 (Virola theiodora)
Synthesis
Manske, Can. J. Res. 5: 592, 1931;
Speeter, J.Am. Chem. Soc. 76:6208, 1954
Chemistry
crystals from ethanol, mp 44.6-46.8°, sol. in dilute acids; picrate mp 169.5-170.5°; methiodide mp 216-217°; fumarate mp 152-152.5°
Pharmacology
entheogenic at 1 mg/kg i.m. (Szára, Experientia 12: 441, 1956; Sai-Halász, Psychiatr. Neurol. 135: 285, 1958)
Legal Status
controlled

Jonathan Ott, Pharmacotheon, p.433


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