Dihexyltryptamine

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 1mg/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

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 100mg 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. "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."

Dihexyltryptamine

Bron en licentie