Metabolism of the recently encountered designer drug,
methylone, in humans and rats

by
Kamata HT, Shima N, Zaitsu K, Kamata T, Miki A,
Nishikawa M, Katagi M, Tsuchihashi H.
Forensic Science Laboratory,
Osaka Prefectural Police HQ, Osaka, Japan.
Xenobiotica. 2006 Aug;36(8):709-23.


ABSTRACT

The urinary metabolites of methylone in humans and rats were investigated by analysing urine specimens from its abuser and after administrating to rats with gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-electrospray ionization mass spectrometry (LC-ESI MS), using authentic standards. The time-course excretion profiles of methylone and its three metabolites in rats were further investigated after a single intraperitoneal dosing of 5 mg kg-1 methylone hydrochloride. Two major metabolic pathways were revealed for both humans and rats as follows: (1) side-chain degradation by N-demethylation to the corresponding primary amine methylenedioxycathinone (MDC), partly conjugated; and (2) demethylenation followed by O-methylation of either a 3- or 4-OH group on the benzene ring to produce 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC), respectively, mostly conjugated. Of these metabolites, HMMC was the most abundant in humans and rats. The cumulative amount of urinary HMMC excreted within the first 48 h in rats was approximately 26% of the dose, and the amount of the parent methylone was not more than 3%. These results demonstrate that the analysis of HMMC will be indispensable for proof of the use of methylone in forensic urinalysis.

Methylone
Methcathinone
Alexander Shulgin
Methylone: structure
Methylone and serotonin
Methylone and the catecholamines
Methylone and monoamine neurotransmission


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