title: Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites.
abstract: The urinary metabolites of 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) in humans have been investigated by analyzing urine specimens from its users. For the unequivocal identification and accurate quantification of its major metabolites, careful analyses were conducted by gas chromatography/mass spectrometry, liquid chromatography/mass spectrometry, and liquid chromatography-tandem mass spectrometry, using authentic standards of each metabolite synthesized. Three major metabolic pathways were revealed as follows: 1) side chain degradation by O-demethylation to form 5-hydroxy-N,N-diisopropyltryptamine (5-OH-DIPT), which would be partly conjugated to its sulfate and glucuronide; 2) direct hydroxylation on position 6 of the aromatic ring of 5-MeO-DIPT, and/or methylation of the hydroxyl group on position 5 after hydroxylation on position 6 of the aromatic ring of 5-OH-DIPT, to produce 6-hydroxy-5-methoxy-N,N-diisopropyltryptamine (6-OH-5-MeO-DIPT), followed by conjugation to its sulfate and glucuronide; and 3) side chain degradation by N-deisopropylation, to the corresponding secondary amine 5-methoxy-N-isopropyltryptamine (5-MeO-NIPT). Of these metabolites, which retain structural characteristics of the parent drug, 5-OH-DIPT and 6-OH-5-MeO-DIPT were found to be more abundant than 5-MeO-NIPT. Although the parent drug 5-MeO-DIPT was detectable even 35 h after dosing, no trace of its N-oxide was detected in any of the specimens examined.
authors.affiliation: Forensic Science Laboratory, Osaka Prefectural Police Headquarters, 1-3-18, Hommachi, Chuo-ku, Osaka 541-0053, Japan. t-kamata@mahoroba.ne.jp.
authors.forename: Tooru
authors.initials: T
authors.lastname: Kamata
authors.forename: Munehiro
authors.initials: M
authors.lastname: Katagi
authors.forename: Hiroe T
authors.initials: HT
authors.lastname: Kamata
authors.forename: Akihiro
authors.initials: A
authors.lastname: Miki
authors.forename: Noriaki
authors.initials: N
authors.lastname: Shima
authors.forename: Kei
authors.initials: K
authors.lastname: Zaitsu
authors.forename: Mayumi
authors.initials: M
authors.lastname: Nishikawa
authors.forename: Einosuke
authors.initials: E
authors.lastname: Tanaka
authors.forename: Katsuya
authors.initials: K
authors.lastname: Honda
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Tsuchihashi
mesh_terms: D008735:5-Methoxytryptamine / Q000031:analogs & derivatives* / Q000378:metabolism / Q000506:poisoning / Q000652:urine; D000328:Adult; D002853:Chromatography, Liquid; D003704:Dementia / Q000139:chemically induced; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000378:metabolism* / Q000506:poisoning / Q000652:urine; D006801:Humans; D008297:Male
chemical_list: D006213:Hallucinogens; C033696:5-methoxy-N,N-diisopropyltryptamine; D008735:5-Methoxytryptamine