N,N-Dimethyltryptamine

Description

N,N-Dimethyltryptamine (DMT) is a plant-based hallucinogen that is outlawed in most countries. DMT was isolated from many species in the 1950s, notably by Pfizer chemists F. A. Hochstein and Anita M. Paradies, who discovered it in the leaves of Prestonia amazonica (aka Haemadictyon amazonicum), which is called “yagé” by inhabitants of the Peruvian Amazon basin.
Hungarian chemist/psychologist Stephen Szará synthesized DMT in 1956 and studied its psychotropic effects in volunteers during that decade. DMT is sometimes called the “spirit molecule”; it produces psychedelic results when it is swallowed, inhaled, injected, or “vaped”. The DMT structure with a hydroxyl group on the benzene ring is the “feel-good” molecule serotonin.
DMT is currently an outlaw, but chemist David Olson and his research team at the University of California, Davis, may have found a legitimate pharmaceutical use for it and other hallucinogens. In an effort to find alternatives to the side effect–prone anesthetic ketamine* for treating depression, the investigators showed that DMT, LSD, and other psychotropics increase the number of synapses in the brain areas of lab animals that regulate emotion and mood.
As with ketamine, the effects are long-lasting and involve a similar signaling pathway. These results are promising, but any commercial drug to arise from them is a long way off.
*Recently reported research indicates that ketamine may require signaling through opioid receptors.

Chemical properties

Tan Solid

The Uses of N,N-Dimethyltryptamine

It is an endogenous Sigma-1 receptor regulator.

The Uses of N,N-Dimethyltryptamine

A labelled endogenous Sigma-1 receptor regulator.

Definition

ChEBI: A tryptamine derivative having two N-methyl substituents on the side-chain.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 3738, 1994 DOI: 10.1021/jo00092a046

General Description

Dimethyltryptamine is a very weak hallucinogen, activeonly by inhalation or injection, with a short duration of action.It possesses pronounced sympathomimetic (NE) sideeffects.

Biological Activity

Endogenous σ 1 receptor ligand and psychoactive plant compound (K i = 14.8 μ M). Binding to σ 1 inhibits voltage-gated Na + channels and is responsible for the behavioral effects of DMT. Also a 5-HT 2A receptor agonist and inhibitor of 5-HT uptake at plasma membrane serotonin transporters (SERT) (K i = 4.0 μ M).