Dihexyltryptamine

Dihexyltryptamine

Clinical data
Other names	N,N-Dihexyltryptamine; DHT
Identifiers
IUPAC name N-hexyl-N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine
PubChem CID	129679089
ChemSpider	102826556
Chemical and physical data
Formula	C22H36N2
Molar mass	328.544 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCCN(CCCCCC)CCC1=CNC2=CC=CC=C21
InChI InChI=1S/C22H36N2/c1-3-5-7-11-16-24(17-12-8-6-4-2)18-15-20-19-23-22-14-10-9-13-21(20)22/h9-10,13-14,19,23H,3-8,11-12,15-18H2,1-2H3 Key:GTQCUMXNKPVMON-UHFFFAOYSA-N

Dihexyltryptamine (DHT), or N,N-dihexyltryptamine, is a drug of the tryptamine family related to serotonergic psychedelics like dimethyltryptamine (DMT). ^{[1] [2]} It is an analogue in the structural series of N,N-dialkylated tryptamines that also includes DMT, diethyltryptamine (DET), dipropyltryptamine (DPT), dibutyltryptamine (DBT), and diamyltryptamine (DAT). ^{[1] [2] [3] [4]}

The drug is active in the conditioned avoidance test and produces dose-dependent hypolocomotion in rodents similarly to psychedelic tryptamines. ^[5] In contrast to its lower homologues like DMT, DET, DPT, and DBT however, DHT was completely inactive in terms of hallucinogenic and other effects at a dose of 1 mg/kg in humans. ^{[1] [2] [6]} In terms of the lower homologues, DMT, DET, and DPT are all described as fully effective hallucinogens, whereas DBT was described as producing only slight hallucinogenic effects. ^{[1] [2] [6] [3]}

DHT was first described by Stephen Szára and colleagues in 1961. ^[6] It was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL , but does not appear to have been synthesized or evaluated by him. ^[3]

References

1. 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).
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. Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
4. 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.
5. Hearst E, Putney F, Szara S (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 27 May 2025.
6. Szara. S. (1961): Correlation between metabolism and behavioral action of psychotropic tryptamine derivatives. Biochem. Pharmacol., 8:32. "N.N-dimethyltryptamine and its N.N-diethyl and N.N-dipropyl homologues produce autonomic symptoms, perceptual, emotional, and thinking disturbances in man (in doses of 1 mg/kg) similar to LSD25 or mescalin but for a much shorter period of time. The corresponding dibutyl derivative causes only very slight symptoms while the dihexyl compound is completely inactive in the same dose."

External links

• DHT - Isomer Design