Dibutyltryptamine

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

Dibutyltryptamine

Clinical data
Other names	N,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
IUPAC name N-butyl-N-[2-(1H-indol-3-yl)ethyl]butan-1-amine
CAS Number	15741-77-2 Y
PubChem CID	27848
ChemSpider	25911 Y
UNII	QFE8WT8WCW
CompTox Dashboard (EPA)	DTXSID40166255
Chemical and physical data
Formula	C18H28N2
Molar mass	272.436 g·mol−1
3D model (JSmol)	Interactive image
Melting point	186 to 188 °C (367 to 370 °F)
SMILES CCCCN(CCCC)CCC1=CNC2=CC=CC=C21
InChI 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 Y Key:LZLJUZWFWYEQLY-UHFFFAOYSA-N Y
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Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported that a dose of 1 mg/kg 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.^{[citation needed]} 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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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.

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.^{[citation needed]}

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.^[4]

See also

• Substituted tryptamine