Dihexyltryptamine

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). 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).

Use and effects

DHT, in contrast to its lower homologues including DMT, DET, DPT, and DBT, was completely inactive in terms of hallucinogenic and other effects at a dose of 1 mg/kg in humans. With regard to the lower homologues, DMT, DET, and DPT are all described as fully effective hallucinogens, whereas DBT was described as producing only slight hallucinogenic effects.

Pharmacology

Pharmacodynamics

The drug is active in the conditioned avoidance test and produces dose-dependent hypolocomotion in rodents similarly to psychedelic tryptamines.

Chemistry

Analogues

Analogues of DHT include diethyltryptamine (DET), dipropyltryptamine (DPT), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), and dibutyltryptamine (DBT), among others.

N-Hexyltryptamine

Chemical structure of N-hexyltrytamine (NHT).

The N-monohexyl analogue of DHT, N-hexyltryptamine (NHT), has also been described. According to Stephen Szara and Alexander Shulgin, this compound was inactive at a dose of up to 100 mg orally.

History

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

See also

References

  1. 1 2 3 4 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. 1 2 3 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).
  3. 1 2 3 4 5 6 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "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."
  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. 1 2 3 Szára S (1961). "104 Correlation between Metabolism and Behavioural Action of Psychotropic Tryptamine Derivatives". Biochemical Pharmacology. 8 (1): 32. doi:10.1016/0006-2952(61)90278-7. 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.
  6. ↑ 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.
  7. 1 2 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.
  8. 1 2 Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Little is known of the monosubstituted tryptamines. N-Methyltryptamine has been mentioned as a minor component in Anadenanthera spp. It has also been identified in the bark of Virola theiodora (Cassidy et al., 1969), a plant that is one of the principal sources of the carbo-line psychotomimetics. In comparison with dimethyltryptamine, mono-methyltryptamine produces less central stimulation in the dog, and the monopropyl homolog [(XXIII), R = n-C3H7] is without activity (Conner, 1954). The n-hexyl homolog [(XXIII), R = n-C6H13] has been found inactive in a limited number of subjects (Szara, 1967). The mono-tert-butyl derivative [(XXIII), R = t-C4H9) has the reputation of oral activity (see above discussion concerning anonymous street knowledge), but dosage details are not known.