Chemistry:Dibutyltryptamine

Dibutyltryptamine (DBT), also known as N,N-dibutyltryptamine (N,N-DBT), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported that a dose of 1 mg/kg DBT by intramuscular injection was active, but less so than dimethyltryptamine (DMT) or diethyltryptamine (DET), producing only slight hallucinogenic effects.

Pharmacology

Pharmacodynamics

DBT is a serotonin receptor agonist in the rat uterus and rat stomach strip, with similar potency as dimethyltryptamine (DMT). It produces the head-twitch response, a behavioral proxy of psychedelic effects, in mice.

Chemistry

DBT is found either as its crystalline hydrochloride salt or as an oily or crystalline base.

Synthesis

The chemical synthesis of DBT has been described.

Isomers

There are four symmetrical isomers of DBT which can be made, or ten isomers in total if unsymmetrical substitution is used. Of these only the n-butyl analogue DBT is known to be active in humans; the isobutyl, sec-butyl, and tert-butyl isomers DIBT, DSBT and DTBT have never been tested and only DBT and DIBT were made by Shulgin.

Chemical structures of DBT and its skeletal isomers

• 
  DBT
• 
  DiBT
• 
  DsBT
• 
  DtBT

Analogues

Analogues of DBT include 4-HO-DBT, 4-HO-DsBT, 5-MeO-DBT, and dihexyltryptamine (DHT), among others.

History

DBT was first described in the scientific literature by 1959.

Society and culture

Legal status

Canada

DBT is not a controlled substance in Canada as of 2025.

United States

DBT is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

• Substituted tryptamine

External links

• DBT - Isomer Design
• DBT - TiHKAL - Erowid
• DBT - TiHKAL - Isomer Design