In vivo metabolism of 5-methoxy-N, N-dimethyltryptamine and N,N-dimethyltryptamine in the rat

Sitaram, Balvant R.; Lockett, Lynn; Talomsin, Rerngjit; Blackman, Graeme L.; McLeod, W. R.

doi:10.1016/0006-2952(87)90118-3

Cited by 64 publications

(85 citation statements)

References 15 publications

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“…Previous studies on the rat reported metabolic routes of DMT and 5-MeO-DMT, which include N-oxidation, N-demethylation, Odemethylation, and oxidative deamination (Sitaram et al, 1987). Based on that previous report, 5-MeO-NIPT, 5-OH-DIPT, and 5-MeO-DIPT-NO were predicted as the major urinary metabolites of 5-MeO-DIPT.…”

Section: Discussionmentioning

confidence: 90%

“…In the previous study by dmd.aspetjournals.org Sitaram et al (1987) on the metabolism of 5-MeO-DMT, an analog of 5-MeO-DIPT, 5-MeO-DMT-N-oxide was identified as the abundant and characteristic urinary metabolite in the rat. This difference is probably attributed to steric interference with N-oxidation on the tertiary nitrogen atom by the two bulky isopropyl moieties, although the possibility of interspecies variations should not be excluded.…”

Section: Discussionmentioning

confidence: 95%

“…Also, a more quantitative experiment using radiolabeled 5-MeO-DIPT in an animal model might be very useful for more detailed survey of the metabolism of 5-MeO-DIPT. It is well known that oxidative N-deamination is a major metabolic pathway for 5-MeO-DMT in the rat (Sitaram et al, 1987) and, thus, it is expected to be an important metabolic pathway for 5-MeO-DIPT in humans. However, possible metabolites like 5-methoxyindoleacetic acid and 5-hydroxyindoleacetic acid, formed by the oxidative deamination, retain few structural characteristics of the parent compound.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, 5-MeO-DIPT was amended into Schedule I of the Controlled Substances Act in 2003 in the United States (DEA, 2003) and was banned in Japan in April 2005. Although research on the metabolism of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in mammals (Sitaram et al, 1987) provides some useful information for analyzing 5-MeO-DIPT metabolites in human body fluids, only a few data have been reported for its metabolism in humans. Recently, "tentative identification" of several metabolites in humans, but without using authentic standards, was reported (Meatherall and Sharma, 2003;Wilson et al, 2005).…”

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confidence: 99%

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METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

Kamata¹,

Katagi²,

Kamata³

et al. 2005

Drug Metab Dispos

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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.

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Section: Discussionmentioning

confidence: 90%

Section: Discussionmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

METABOLISM OF THE PSYCHOTOMIMETIC TRYPTAMINE DERIVATIVE 5-METHOXY-N,N-DIISOPROPYLTRYPTAMINE IN HUMANS: IDENTIFICATION AND QUANTIFICATION OF ITS URINARY METABOLITES

Kamata¹,

Katagi²,

Kamata³

et al. 2005

Drug Metab Dispos

View full text Add to dashboard Cite

show abstract

“…The decrease (ϳ50%) in systemic clearance at higher doses indicates the presence of nonlinearity in 5-MeO-DMT elimination. Given the facts that metabolic elimination is the major elimination pathway for 5-MeO-DMT and MAO-A-mediated deamination is the main metabolic pathway for 5-MeO-DMT (Agurell et al, 1969;Squires, 1975;Suzuki et al, 1981;Sitaram et al, 1987b;Shen et al, 2009Shen et al, , 2010b enedioxymethamphetamine ("Ecstasy"), exhibits nonlinear pharmacokinetics in rodents, nonhuman primates, and humans, which may influence the likelihood and severity of 3,4-methylenedioxymethamphetamine toxicities (de la Torre et al, 2000;Mueller et al, 2008;Baumann et al, 2009). The current study clearly demonstrates nonlinear pharmacokinetics for 5-MeO-DMT in mice (Figs.…”

Section: Discussionmentioning

confidence: 99%