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Carter MF, Shulgin AT. 
“N,N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity”. 
Commun Psychopharmacol. 1980 May;4(5):363-9.
N,N-Disubstituted tryptamines have been recognized as a major family of centrally active hallucinogens or psychotomimetic agents. A series of homologs, with straight-chain substituents on the basic nitrogen and unsubstituted in the aromatic ring, has been shown to contain moderately potent hallucinogens. N,N-Dimethyltryptamine (DMT), N,N-diethyltryptamine (DET), N,N-di(n)propyltryptamine (DPT), and its unsaturated counterpart N,N-diallyltryptamine are all parenterally active in man, with an effective dose range of 50 to 100 mg(1). Because of the short duration of action of these compounds (less than 3 hrs.) two of them (DET(2) and DPT(1)) have been studied as psychotherapeutic agents. Oxygenation of the 4-position produces the alkaloid psilocin (4-hydroxy-N,N-dimethyltryptamine) and psilocybin (the phosphate ester of psilocin). These two bases, and the corresponding N,N-diethyl homologs CZ-74 and CEY-19, are orally active hallucinogens effective in man in the 5 - 10 mg range(4). The relocation of the oxygen function to the 5-position (to produce 5-methoxy-N,N-dimethyltryptamine, 5-MeO-DMT) maintains the potency of the related positional isomers but reinvokes the requirement of parenteral administration for effectiveness(5).

The reasons for the lack of oral activity of the 5-H and 5-OCH3 substituted families of N, N-dialkyltryptamines have not yet been satisfactorily established. The metabolism of such compounds usually follows either of two routes; dealkylation or oxidative deamination to the corresponding indole-3-acetic acid. It has been assumed that the oral ineffectiveness of these compounds is due to a metabolic transformation which occurs before an active site in the brain can be reached.
Notes # : Scanned as part of the Shulgin Archiving Project: Shulgin Collection. Note that the citation for this is different than PubMed's version of the citation. (Shulgin appears as the first author in PubMed's entry.)
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