Diamyltryptamine

Not to be confused with Diallyltryptamine.

Diamyltryptamine (DAT), also known as N,N-dipentyltryptamine, is a chemical compound of the tryptamine family related to dimethyltryptamine (DMT).^[1][2] It is part of the homologous series of tryptamines that includes DMT, diethyltryptamine (DET), dipropyltryptamine (DPT), dibutyltryptamine (DBT), DAT itself, and dihexyltryptamine (DHT).^[1][3][4]

Diamyltryptamine

Clinical data
Other names	DAT; DAmT; N,N-Diamyltryptamine; Dipentyltryptamine; N,N-Dipentyltryptamine; DPeT
ATC code	None
Pharmacokinetic data
Onset of action	Unknown[1]
Duration of action	Unknown[1]
Identifiers
IUPAC name N-[2-(1H-indol-3-yl)ethyl]-N-pentylpentan-1-amine
Chemical and physical data
Formula	C20H32N2
Molar mass	300.490 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCN(CCc1c[nH]c2c1cccc2)CCCCC
InChI InChI=1S/C20H32N2/c1-3-5-9-14-22(15-10-6-4-2)16-13-18-17-21-20-12-8-7-11-19(18)20/h7-8,11-12,17,21H,3-6,9-10,13-16H2,1-2H3 Key:AXUJSLZQVYSFBL-UHFFFAOYSA-N

Use and effects

The compound was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), but he does not appear to have synthesized or tested it.^[1] Relatedly, the properties and effects of DAT are unknown.^[1] However, it is known that whereas DMT, DET, and DPT are fully effective psychedelics, DBT showed only weak psychedelic effects and DHT was inactive.^[3][4][1]

Chemistry

Analogues

N-Amyltryptamine

Chemical structure of N-amyltrytamine (NAT).

The N-monoamyl analogue of DAT, N-amyltryptamine (NAT), has also been described.^[1][5] According to Stephen Szara and Alexander Shulgin, this compound was inactive at a dose of up to 100 mg orally.^[1][5]

History

DAT was first described in the scientific literature by Stephen Szara and colleagues in 1962, who studied its metabolism (specifically 6-hydroxylation) in vitro.^[2]

See also

• Substituted tryptamine
• Dihexyltryptamine (DHT)