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Stereochemistry of the Metabolism of MDMA to MDA

Stereochemistry of the Metabolism of MDMA to MDA

R L Fitzgerald, R V Blanke, J A Rosecrans, R A Glennon

Life Sci. 1989;45(4):295-301.

PMID: 2569654

Abstract:

The chiral derivatizing reagent N-trifluoroacetyl-L-prolyl chloride (LTPC) was used to form diastereomers of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) which were resolved on an achiral gas chromatographic column using a mass spectrometer as a detector. Rats were subcutaneously dosed with 40 mg/kg of (+/-) MDMA.HCl and blood was obtained by decapitation four hours after dosing. Plasma was separated and extracted. The extract was derivatized on-column with LTPC. In addition to the two MDMA isomers, the demethylated metabolites, S(+) and R(-)-MDA were identified. In all experimental groups (male rats, food deprived male rats, female rats, post partum female rats, and mice) dosed with racemic MDMA, higher levels of the S(+) isomer of MDA relative to the R(-) MDA isomer were observed. This may be significant since it has been shown that the S(+) isomer of MDMA is the more neurotoxic isomer of the racemic drug of abuse MDMA.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP159717687	N-(7-Nitro-4-benzofurazanyl)-L-prolyl chloride		159717-68-7	Price

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