Urinary excretion of 5-methoxy-N,N-dimethyltryptamine, N,N-dimethyltryptamine and their N-oxides in the rat

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

doi:10.1016/0006-2952(87)90159-6

Cited by 33 publications

(41 citation statements)

References 12 publications

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“…It has been demonstrated that iproniazid pretreatment (MAO-A inhibition) increases the levels of DMT in vivo in rat brain, liver, kidney, blood, as well as DMT-NO in rat liver (Sitaram et al, 1987b), and increases the urinary excretion of DMT, DMT-NO and NMT in rodents (Sitaram et al, 1987a). These data suggest that MAO inhibition may shift metabolism to these other routes as part of a possible compensatory metabolic mechanism.…”

Section: Major Constituents and Metabolites Of Ayahuasca In Urinementioning

confidence: 93%

“…Sitaram et al found an approximately 10 times higher concentration of DMT-NO compared with DMT following iproniazid pretreatment in rodents (Sitaram et al, 1987a) and noted a 6 times higher concentration of DMT-NO compared with DMT in control animals when no MAOI was administered. This suggests that DMT-NO may represent a major in vivo metabolite of DMT and may, thus, serve as a better marker for endogenous DMT production and metabolism in mammals as well (Barker et al, 1980(Barker et al, , 1981Sitaram et al, 1987a).The data from the present study represent the first report of DMT-NO as a metabolite of DMT in the urine of humans following ayahuasca administration or, for that matter, DMT alone. This finding has implications for the further study of DMT in general, particularly its occurrence as a naturally occurring trace amine in man.…”

Section: Major Constituents and Metabolites Of Ayahuasca In Urinementioning

confidence: 96%

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Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine

McIlhenny

Riba

Barbanoj

et al. 2010

Biomedical Chromatography

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Ayahuasca, also known as caapi or yage among various South American groups, holds a highly esteemed and millennia-old position in these cultures' medical and religious pharmacopeia. There is now an increasing interest in the potential for modern medical applications of ayahuasca, as well as concerns regarding its increasing potential for abuse. Toxicological and clinical research to address these issues will require information regarding its metabolism and clearance. Thus, a rapid, sensitive and specific method for characterization and quantitation of the major constituents and of the metabolites of ayahuasca in urine is needed. The present research provides a protocol for conducting such analyses. The characteristics of the method, conducted by sample dilution and using HPLC-electrospray ionization (ESI)-selected reaction monitoring (SRM)-tandem mass spectrometry, are presented. The application of the analytical protocol to urine samples collected from three individuals that were administered ayahuasca has also been demonstrated. The data show that the major metabolite of the hallucinogenic component of ayahuasca, N,N-dimethyltryptamine (DMT), is the corresponding N-oxide, the first time this metabolite has been described in in vivo studies in humans. Further, very little DMT was detected in urine, despite the inhibition of monoamine oxidase afforded by the presence of the harmala alkaloids in ayahuasca. The major harmala alkaloid excreted was tetrahydroharmine. Other excretion products and metabolites were also identified and quantified. The method described would be suitable for use in further toxicological and clinical research on ayahuasca.

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Section: Major Constituents and Metabolites Of Ayahuasca In Urinementioning

confidence: 93%

Section: Major Constituents and Metabolites Of Ayahuasca In Urinementioning

confidence: 96%

Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine

McIlhenny

Riba

Barbanoj

et al. 2010

Biomedical Chromatography

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“…Urine directly activates mTAAR4, mTAAR5, mTAAR7f, rTAAR8c, and rTAAR9 [4,33,35], with mTAAR4 and mTAAR5 detecting species-specific metabolites (see below). Agonists for mTAAR3 (isopentylamine) and mTAAR7e (5-methoxy- N,N -dimethyltryptamine) are also reported in urine [36,37]. Isopentylamine is a biogenic amine produced by leucine decarboxylation and its ecological salience is unclear, as it is innately aversive to rodents [38].…”

Section: Taars That Recognize Ethological Odorsmentioning

confidence: 99%

Trace amine-associated receptors: ligands, neural circuits, and behaviors

Liberles

2015

Current Opinion in Neurobiology

124

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Trace amine-associated receptors (TAARs) are G Protein-Coupled Receptors that function as vertebrate olfactory receptors. Like odorant receptors, TAARs constitute an ever-evolving sensory subsystem, with individual TAARs recognizing particular chemicals and some evoking stereotyped behaviors. Several TAARs mediate aversion or attraction towards volatile amines that include the mouse odor trimethylamine, the predator odor 2-phenylethylamine, and the death-associated odor cadaverine. TAAR-expressing sensory neurons achieve monoallelic receptor expression, use canonical olfactory signaling molecules, and target a dedicated olfactory bulb region. In mouse, TAAR4 and TAAR5 are encoded by adjacent genes and localize to adjacent glomeruli, yet mediate opposing behaviors. Future studies are needed to understand how TAAR-expressing sensory neurons engage higher-order neural circuits to encode odor valence.

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“…Unfortunately, with the exception of forensic case studies (Ikeda, Sekiguchi, Fujita, Yamadera, & Kog, 2005;Wilson, McGeorge, Smolinske, & Meatherall, 2005)) anecdotes (Shulgrin & Shulgrin, 1997)) and toxicological investigations (e.g., Sitaram, Lockett, Blackman, & McLeod, 1987;Meatherall & Sharma, 2003;Smolinske, Rastogi, & Schenkel, 2003)) there is little published information on the effects of 5-MeO-DIPT, and little is known of the consequences of its use or specific central nervous system effects. Owing to its increased use among adolescents, the possible risks on development in vulnerable adolescents may be of major concern, especially as a societal health problem.…”

mentioning

confidence: 97%

An Examination of the Effects of 5-Methoxy-N,N-di(iso)propyltryptamine Hydrochloride (Foxy) on Cognitive Development in Rats

Compton

Selinger²,

Testa

et al. 2006

Psychol Rep

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The hallucinogenic "designer drug" known as Foxy or Methoxy Foxy and formally know as 5-Methoxy-N,N-di(iso)propyltryptamine hydrochloride (5-MeO-DIPT) is rapidly gaining popularity among recreational users. However, little is known about the consequences of its use on neuropsychological development or behavior. During one of two adolescent periods, the rats were given repeated injections of either saline or 5 mg/kg of 5-MeO-DIPT. Once the animals reached 80 days of age, they were trained and tested on a number of tasks designed to assess the effects of 5-MeO-DIPT, if any, on memory tasks with spatial components that presumably involve declarative memory systems and on a nonspatial task that is considered sensitive to disruptions in nondeclarative memory. With one exception, both the 5-MeO-DIPT- and saline-treated rats were able to master the spatial navigation tests at comparable rates. However, the performance of the drug-treated rats was markedly inferior to that of the control animals on a response-learning task, suggesting a lack of flexibility in adapting their responses to changing task demands. This could indicate reductions in serotonin activity in the forebrain similar to the effects of studied drugs such as methylenedioxymethamphetamine (MDMA), suggesting 5-MeO-DIPT may act as a toxin compromising serotoninergic systems in the brain.

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Urinary excretion of 5-methoxy-N,N-dimethyltryptamine, N,N-dimethyltryptamine and their N-oxides in the rat

Cited by 33 publications

References 12 publications

Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine

Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine

Trace amine-associated receptors: ligands, neural circuits, and behaviors

An Examination of the Effects of 5-Methoxy-N,N-di(iso)propyltryptamine Hydrochloride (Foxy) on Cognitive Development in Rats

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