PT - JOURNAL ARTICLE AU - Tooru Kamata AU - Munehiro Katagi AU - Hiroe T. Kamata AU - Akihiro Miki AU - Noriaki Shima AU - Kei Zaitsu AU - Mayumi Nishikawa AU - Einosuke Tanaka AU - Katsuya Honda AU - Hitoshi Tsuchihashi TI - METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-<em>N</em>,<em>N</em>-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES AID - 10.1124/dmd.105.005835 DP - 2006 Feb 01 TA - Drug Metabolism and Disposition PG - 281--287 VI - 34 IP - 2 4099 - http://dmd.aspetjournals.org/content/34/2/281.short 4100 - http://dmd.aspetjournals.org/content/34/2/281.full SO - Drug Metab Dispos2006 Feb 01; 34 AB - 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. The American Society for Pharmacology and Experimental Therapeutics