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Dihexyltryptamine

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Dihexyltryptamine
Clinical data
Other namesN,N-Dihexyltryptamine; DHT
Identifiers
  • N-hexyl-N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC22H36N2
Molar mass328.544 g·mol−1
3D model (JSmol)
  • CCCCCCN(CCCCCC)CCC1=CNC2=CC=CC=C21
  • 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

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  1. ^ a b c d 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. ^ a b c d 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. ^ a b c 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. ^ a b c 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."
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