DHT, in contrast to its lowerhomologues including DMT, DET, DPT, and DBT, was completely inactive in terms ofhallucinogenic and other effects at a dose of 1mg/kg in humans.[1][2][5] 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.[1][2][5][3]
^abcdNichols 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.ISBN978-0-89004-990-7.OCLC10324237.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).
^abcdBrimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN978-0-85608-011-1.OCLC2176880.OL4850660M.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).
^abcdefShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN0-9630096-9-9.OCLC38503252. "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."
^abcSzara. 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."
