Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites.
Tooru Kamata, Munehiro Katagi, Hiroe T Kamata, Akihiro Miki, Noriaki Shima, Kei Zaitsu, Mayumi Nishikawa, Einosuke Tanaka, Katsuya Honda, Hitoshi Tsuchihashi
Drug metabolism and disposition: the biological fate of chemicals February 1, 2006 DOI: 10.1124/dmd.105.005835 via PubMed
Summary
AI-generated from the abstractThe body breaks down the psychedelic drug 5-MeO-DIPT (also known as 'Foxy') through three main pathways: removal of a methyl group to form 5-OH-DIPT, which is then often conjugated; direct addition of a hydroxyl group to the ring, sometimes followed by methylation, producing 6-OH-5-MeO-DIPT; and removal of an isopropyl group to form 5-MeO-NIPT. The first two metabolites are more abundant than the third. The parent drug can still be detected in urine up to 35 hours after use, but no N-oxide form was found.
Study at a glance
| Characteristics | Observational study Peer reviewed |
|---|---|
| Population | Human users of 5-MeO-DIPT |
| Intervention | 5-MeO-DIPT |
| Key finding | The three major metabolic pathways of 5-MeO-DIPT in humans are O-demethylation, direct hydroxylation, and N-deisopropylation, with 5-OH-DIPT and 6-OH-5-MeO-DIPT being more abundant than 5-MeO-NIPT. |
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.