Dibutyltryptamine

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Dibutyltryptamine
Dibutyltryptamine.svg
Clinical data
Other namesN,N-Dibutyltryptamine; DBT; N,N-DBT
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • N-butyl-N-[2-(1H-indol-3-yl)ethyl]butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H28N2
Molar mass 272.436 g·mol−1
3D model (JSmol)
Melting point 186 to 188 °C (367 to 370 °F)
  • CCCCN(CCCC)CCC1=CNC2=CC=CC=C21
  • InChI=1S/C18H28N2/c1-3-5-12-20(13-6-4-2)14-11-16-15-19-18-10-8-7-9-17(16)18/h7-10,15,19H,3-6,11-14H2,1-2H3 Yes check.svgY
  • Key:LZLJUZWFWYEQLY-UHFFFAOYSA-N Yes check.svgY
   (verify)

Dibutyltryptamine (DBT), also known as N,N-dibutyltryptamine (N,N-DBT), is a psychedelic drug of the tryptamine family. [1] It was synthesized by the chemist Alexander Shulgin and described in his book TiHKAL (Tryptamines i Have Known And Loved) . [1]

Contents

Use and effects

Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than DMT or DET. [1] [2] This suggests that an active dosage 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 produces the head-twitch response in mice. [3]

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. 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.

DBT isomers.svg

The unsymmetrical isomers BIBT, BSBT, BTBT, IBSBT, IBTBT and SBTBT are also possible but have never been made and no predictions have been made about their activity. Shulgin speculates that the s-butyl isomer DSBT may be more potent than the straight chain compound DBT, but that the more highly branched DIBT and DTBT would probably be inactive due to the bulk of the substituent group. As for longer chain compounds than butyl, they have not been made and would probably be inactive. Shulgin mentions that the monohexyl compound NHT is without activity. However the unsymmetrical compounds such as methylbutyltryptamine show more promise, and a wide range of possible compounds could be made by pairing the various butyl isomers with methyl, ethyl, propyl, isopropyl or allyl groups

See also

References

  1. 1 2 3 4 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. ↑ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. 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. ↑ Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, et al. (June 2019). "Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice". Biomolecules & Therapeutics. 28: 83–91. doi:10.4062/biomolther.2019.049. PMC   6939696 . PMID   31230432.
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