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Fundamental #13: Note changes in health over time
that may be related to psychoactive drug use.
Profiles of Psychedelic Drugs - DMT
Vol 8 (No. 2) Apr-Jun 1976, 167-168
With this issue we are introducing a new column which will present thumbnail sketches of the known psychedelic drugs. Rather than an attempt to review the existing literature on each drug (some would have hundreds of references and some perhaps two), the facts that are known concerning history, human pharmacology and human psychopharmacology will be amalgamated into a "profile." The drugs to be presented will be chosen randomly, rather than with preference given to popularity, unusual potency, or current availability. Botanical mixtures will not be considered as such, but as their known active compnents. As there are upwards of a hundred psychedelic drugs currently known, it is expected that these "profiles" will eventually form an extensive reference atlas of compactly presented drug information.


1. DMT

Description and properties:

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, Anadenanthera, 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 100 ng/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 1000 mg. With intramuscular injection, there is an abrupt threshold of activity shown with 30 mg, and a complete psychedelic experience results from the administration of 50-70 mg (75 mg subcutaneously, 30 mg 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 minute, 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 150 mg 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.

DMT

[Excerpt from a pharmacology textbook published in 1988]

Chemical structure and source:

This is the prototype member of the tryptamine subclass of indole derivatives. The structural formula is:
                         /\       (CH2)2-N(CH3)2
                        // \ ____/
                       |   ||   ||
                       |   ||   ||
                        \\ /\   / 
                         \/  \N/
                              H

                   N,N-dimethyltryptamine
  
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, mentioned above; it is also found in the seeds of Anadenanthera peregina; in the seeds of the vine Mimosa hostilis, used in easternBrazil 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 oxydase inhibitors to become active orally.

Dose:

First strong effects are felt at about 50 mg, 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 and 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:

              /\       (CH2)2-N(C2H5)2     /\      (CH2)2-N(CH2CH2CH2)2
             // \ ____/                   // \ ____/
            |   ||   ||                  |   ||   ||
            |   ||   ||                  |   ||   ||
             \\ /\   /                    \\ /\   / 
              \/  \N/                      \/  \N/
                   H                            H

        N,N-diethyltryptamine          N,N-dipropyltryptamine
  
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 30 mg, and for four to six hours at doses in the range of 60 to 150 mg. 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. [Erowid Note: See note below.] Dibutyltryptamine (DBT) and higher substitutions are inert, but other synthetic drugs related to DMT may be psychoactive.




Erowid Notes (not part of original paper)

June 2006: Alexander Shulgin later retracted the claim that DET was not orally active. The DET entry in TiHKAL, from 1997, specifically addresses the discrepancy. Please see that entry for more details, but he begins his Commentary with:
"I have to bear the responsibility for much of the mythology that maintains that DET is only active by some parenteral route. All of the published human studies that explicitly mentioned dose and dosage, involved intramuscular administrations. Most of the people with whom I had private conversations about this material had evaluated it through the smoking route. It was only recently that I began to hear of oral trials. I had assumed that it was inactive orally, and had said so in a number of reviews that I had published over the years. As they say in Latin, mea culpa." (Shulgin A. TiHKAL. Chemical #3. 1997)

Thanks to DidierM for pointing this out.