Urinary Excretion Profiles of 5-Methoxy-N,N-diisopropyltryptamine and Its Relevant Metabolites in Humans

In urine from six users of the psychedelic tryptamine 5-MeO-DIPT, three metabolites—5-OH-DIPT, 6-OH-5-MeO-DIPT, and 5-MeO-NIPT—were identified. Using enzymatic hydrolysis with ascorbic acid to prevent degradation, conjugated forms (sulfates and glucuronides) of the hydroxylated metabolites were fully cleaved, greatly increasing their detection, especially for 6-OH-5-MeO-DIPT. After hydrolysis, concentrations of 5-OH-DIPT ranged from 0.01 to 47 μg/ml and 6-OH-5-MeO-DIPT up to 69 μg/ml, while the parent drug and 5-MeO-NIPT remained below 1.7 and 3.5 μg/ml, respectively. Metabolites were detectable longer than the parent compound: 5-OH-DIPT up to 80 hours, 6-OH-5-MeO-DIPT and 5-MeO-NIPT up to 60 hours, versus 35 hours for 5-MeO-DIPT.

Study at a glance

Abstract

5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), a psychotomimetic tryptamine derivative, and its relevant metabolites have been determined in eleven urine specimens from six 5-MeO-DIPT users, and their excretion profiles have been investigated by gas chromatography/mass spectrometry (GC/MS) and liquid chromatography/mass spectrometry (LC/MS). Three metabolites, 5-hydroxy-N,N-diisopropyltryptamine (5-OH-DIPT), 6-hydroxy-5-methoxy-N,N-diisopropyltryptamine (6-OH-5-MeO-DIPT), and 5-methoxy-N-isopropyltryptamine (5-MeO-NIPT) were determined in the urine specimens. Urinary conjugated metabolites, both sulfates and glucuronides of 5-OH-DIPT and 6-OH-5-MeO-DIPT, were hydrolyzed completely by the use of Helix pomatia sulfatase/β-glucuronidase. Degradation of 6-OH-5-MeO-DIPT during incubation for hydrolysis was successfully prevented by the addition of ascorbic acid. The hydrolysis treatment increased the detection amounts of 5-OH-DIPT and 6-OH-5-MeO-DIPT in most of the specimens, and the increase in 6-OH-5-MeO-DIPT was more drastic than that in 5-OH-DIPT. The concentrations of 5-MeO-DIPT (<1.7 μg/ml) and 5-MeO-NIPT (<3.5 μg/ml) were lower than those of 5-OH-DIPT (0.01-47 μg/ml) and 6-OH-5-MeO-DIPT (<69 μg/ml) detected after hydrolysis (the totals of their free and conjugated forms). These metabolites were detectable over longer periods post intake than the parent drug; 35 hr for 5-MeO-DIPT, 80 hr for 5-OH-DIPT, and 60 hr for 6-OH-5-MeO-DIPT and 5-MeO-NIPT.