Metabolic fate of mescaline in man

Charalampous, Kyriakos; Walker, K. E.; Kinross-Wright, John

doi:10.1007/bf00427703

Cited by 80 publications

(32 citation statements)

References 9 publications

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“…for 2C-T-2, 42,49 2C-T-7, 39 for 2C-B, 48,71 or for mescaline. 75 The metabolic pathways of 2C-I in rats described here are similar to those of the related halogen 2C compound 2C-B in rats or mice. 48,51,71 Detection by GC/MS within the STA 2C-I and its metabolites were separated by GC and identified by full-scan MS. Mass chromatography with the ions m/z 290, 349, 276, and 335 was used to indicate the presence of 2C-I and its main metabolites.…”

Section: Proposed Metabolic Pathwaysmentioning

confidence: 78%

New designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques

et al. 2006

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Studies are described on the metabolism and the toxicological analysis of the phenethylamine-derived designer drug 4-iodo-2,5-dimethoxy-beta-phenethylamine (2C-I) in rat urine using gas chromatographic/mass spectrometric (GC/MS) techniques, and for a particular question, using capillary electrophoretic/mass spectrometric (CE/MS) techniques. The identified metabolites indicated that 2C-I was metabolized on the one hand by O-demethylation in position 2 and 5, respectively, followed either by N-acetylation or by deamination with subsequent oxidation to the corresponding acid or reduction to the corresponding alcohol, respectively. The latter metabolite was hydroxylated in beta-position and further oxidized to the corresponding oxo metabolite. On the other hand, 2C-I was metabolized by deamination with subsequent oxidation to the corresponding acid or reduction to the corresponding alcohol, respectively. 2C-I and most of its metabolites were partially excreted in conjugated form. The authors' systematic toxicological analysis (STA) procedure using full-scan GC/MS after acid hydrolysis, liquid-liquid extraction and microwave-assisted acetylation allowed the detection of an intake of a dose of 2C-I in rat urine that corresponds to a common drug users' dose. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C-I in human urine.

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Section: Proposed Metabolic Pathwaysmentioning

confidence: 78%

New designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques

et al. 2006

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“…Such conjugation was concluded because the peak areas of these metabolites were more abundant after glucuronidase and sulfatase hydrolysis. The latter pathway has also been described for other psychotropic amines such as 2C-T-7, 7 2C-B, 24 mescaline 45 or amphetamine-derived designer drugs. 43,50,51 In summary, during the presented study, the 2C-T-2 metabolites already described by Lin et al 25 could be confirmed.…”

Section: ) N-trifluoroacetyl-25-dimethoxy-4-ethylsulfonyl-mentioning

confidence: 92%

New designer drug 2,5‐dimethoxy‐4‐ethylthio‐β‐phenethylamine (2C‐T‐2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry

et al. 2005

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Studies are described on the metabolism and the toxicological analysis of the phenethylamine-derived designer drug 2,5-dimethoxy-4-ethylthio-beta-phenethylamine (2C-T-2) in rat urine using gas chromatography/mass spectrometry (GC/MS) after enzymatic cleavage of conjugates, liquid-liquid extraction and derivatization. The structures of 14 metabolites were assigned tentatively by detailed interpretation of their mass spectra. Identification of these metabolites indicated that 2C-T-2 was metabolized by sulfoxidation followed by N-acetylation and either hydroxylation of the S-ethyl side chain or demethylation of one methoxy group, O-demethylation of the parent compound followed by N-acetylation and sulfoxidation, deamination followed by reduction to the corresponding alcohol followed by partial glucuronidation and/or sulfation or by oxidation to the corresponding acid followed either by partial glucuronidation or by degradation to the corresponding benzoic acid derivative followed by partial glucuronidation. Furthermore, 2C-T-2 was metabolized by N-acetylation of the parent compound followed either by O-demethylation and sulfoxidation or by S-dealkylation, S-methylation and sulfoxidation. The authors' systematic toxicological analysis (STA) procedure using full-scan GC/MS after acid hydrolysis, liquid-liquid extraction microwave-assisted acetylation allowed the detection of an intake of a dose of 2C-T-2 in rat urine, which corresponds to a common drug users' dose. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C-T-2 in human urine.

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“…3,4,5-trimethoxyphenylacetic acid on columns containing dowex 50 W-X4 previously buffered at pH 5.8. The details are given elsewhere (5,6). The radioactivity was determined in a Nuclear Chicago Mark II Liquid Scintillation System using l3JBa as an external standard.…”

Section: Extraction and Determination Of Radioactivitymentioning

confidence: 99%

Effect of clozapine and molindone on plasma and brain levels of mescaline in mice

Shah

Gulati

1984

European Journal of Drug Metabolism and Pharmacokinetics

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Levels of unchanged mescaline were examined in the plasma and brain of albino Swiss-Webster mice pretreated with various doses of either clozapine or molindone. In clozapine treated mice, the mescaline levels were statistically significantly higher at 2 and 3 h with 7.5 and 15.0 mg/kg and at 1, 2 and 3 h with 30 mg/kg. Molindone at 4.0 and 8.0 mg/kg produced no significant effect; at 16.0 and 48.0 mg/kg, the levels were significantly higher at 1 and 2 h. Elevated brain levels of mescaline by clozapine and molindone indicate an adverse metabolic interaction between a hallucinogen and drugs that are commonly used to treat mescaline-induced psychosis.

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Metabolic fate of mescaline in man

Cited by 80 publications

References 9 publications

New designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques

New designer drug 4‐iodo‐2,5‐dimethoxy‐β‐phenethylamine (2C‐I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques

New designer drug 2,5‐dimethoxy‐4‐ethylthio‐β‐phenethylamine (2C‐T‐2): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry

Effect of clozapine and molindone on plasma and brain levels of mescaline in mice

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