Chemistry:Dibutyltryptamine

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Dibutyltryptamine (DBT), also known as N,N-dibutyltryptamine (N,N-DBT), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).[1]

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).[1][2] This suggests that an active dose of DBT will be in the 100 mg range. It has been sold as a "research chemical" and has been confirmed to be an active hallucinogen, although somewhat weaker than other similar tryptamine derivatives.[citation needed]

Interactions

Pharmacology

Pharmacodynamics

DBT is a serotonin receptor agonist in the rat uterus and rat stomach strip, with similar potency as dimethyltryptamine (DMT).[3] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in mice.[4]

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.[1]

Isomers

There are four symmetrical isomers of DBT which can be made, or ten isomers in total if unsymmetrical substitution is used.[1] 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.[1]

Chemical structures of DBT and its skeletal isomers


Analogues

Analogues of DBT include 4-HO-DBT, 4-HO-DsBT, 5-MeO-DBT, and dihexyltryptamine (DHT), among others.[1]

History

DBT was first described in the scientific literature by 1959.[3]

Society and culture

Canada

DBT is not a controlled substance in Canada as of 2025.[5]

United States

DBT is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  2. ↑ "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "The N,N-dibutyl derivative (4.11) showed a considerable decrease in activity, while increasing the chain length to N,N-dihexyl (4.12) abolished hallucinogenic effects in man (Szara, 1961b)." 
  3. ↑ 3.0 3.1 "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". Br J Pharmacol Chemother 14 (1): 99–107. March 1959. doi:10.1111/j.1476-5381.1959.tb00934.x. PMID 13651585. 
  4. ↑ "Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice". Biomolecules & Therapeutics 28: 83–91. June 2019. doi:10.4062/biomolther.2019.049. PMID 31230432. 
  5. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  6. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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