Diamyltryptamine

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]

Other namesDAT; DAmT; N,N-Diamyltryptamine; Dipentyltryptamine; N,N-Dipentyltryptamine; DPeT

ATC code

None

Onset of actionUnknown^[1]

Duration of actionUnknown^[1]

Quick facts Clinical data, Other names ...

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]

References

[1]
Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "Diamyltryptamine". What kinds of homologues of DMT can exist out there on that tryptamine nitrogen? Methyls, ethyls, propyls, butyls? These are already part of this story, known as DMT, DET, DPT and DBT. The diisobutyl analogue of DBT may best be called DIBT and it comes from indol-3-yl-N,N-diisobutylglyoxylamide and LAH in a manner parallel to the DBT procedure given above. The HCl salt has a mp of 202–204 °C. The pairs of alkyl groups can go on and on forever, but the activity seems to drop off as they get longer. How about a pair of 5-carbon chains? Diamyltryptamine? DAT? I certainly can't use the alternate name dipentyltryptamine, as that would be in conflict with DPT which has already established a prior claim for use with dipropyltryptamine. And there is still some possible ambiguity in that there is one mention in the literature that N,N-diallyltryptamine is active, but neither dosage nor route was mentioned. Maybe it should be DALT. For carbon chains that are 7-carbons long, there can only be DST for diseptyltryptamine. The synonymous diheptyltryptamine would require DHT, and this has already been usurped by the 6-carbon job, dihexyltryptamine. And as to trying to name anything higher, such as the N,N-dioctyltryptamine, forget it. [...] Both the mono-amyl and the mono-hexylamines have been described (NAT and NHT), both having been made by the glyoxylamide process. These, too, as has been mentioned above, it appears to be inactive in man, as reported by Stephen Szara at the famous "Ethnopharmacologic Search for Psychoactive Drugs" conference, organized by the late Dan Efron of the National Institute of Mental Health, in San Francisco, in 1967.
[2]
Szara S, Hearst E, Putney F (1962). "Metabolism and behavioural action of psychotropic tryptamine homologues". International Journal of Neuropharmacology. 1 (1–3): 111–117. doi:10.1016/0028-3908(62)90015-1. Retrieved 3 November 2025.
[3]
Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. Szara and co-workers (221,223,225) noted psychotomimetic activity for N,N-diethyltryptamine (DET; 38) at a dose of 1 mg/kg. [...] N,N-Dipropyltryptamine (DPT; 39) is also hallucinogenic in man at 1 mg/kg (222). [...] Branching of the propyl groups results in N,N-diisopropyltryptamine (DIPT; 40), which is orally active at 20 to 50 mg (202). N,N-Dibutyltryptamine (DBT; 41) and N,N-dihexyltryptamine (DHT; 42) have been examined only briefly. At 1 mg/kg, DBT produced only slight perceptual, emotional, and thinking disturbances in man, while DHT at the same dose was completely inactive (222).
[4]
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).
[5]
Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.