| |
Published:
Journal of Analytical Toxicology,
ISSN 0146-4760,
Volume 27, Number 8, November/December,
pp. 560-568
Piperazine-Derived Designer Drug 1-(3-Chlorophenyl)piperazine
(mCPP): GC–MS Studies on its Metabolism and its Toxicological Detection
in Rat Urine Including Analytical Differentiation from its Precursor Drugs
Trazodone and Nefazodone
Roland F. Staack and Hans H. Maurer
Department of Experimental and Clinical Toxicology, Institute of Experimental
and Clinical Pharmacology and Toxicology, University of Saarland, D-66421 Homburg
(Saar), Germany
Studies on the metabolism and the toxicological analysis of the
piperazine-derived designer drug 1-(3-chlorophenyl)piperazine (mCPP) in rat
urine using gas chromatography–mass spectrometry (GC–MS) are described.
mCPP was extensively metabolized, mainly by hydroxylation of the aromatic ring
and by degradation of the piperazine moiety to the following metabolites: two
hydroxy-mCPP isomers, N-(3-chlorophenyl)ethylenediamine, 3-chloroaniline, and
two hydroxy-3-chloroaniline isomers. The hydroxy-mCPP metabolites were partially
excreted as the corresponding glucuronides and/or sulfates, and the aniline
derivatives were partially acetylated to N-acetyl-hydroxy-3-chloroaniline isomers
and N-acetyl-3-chloroaniline. Our systematic toxicological analysis (STA) procedure
using full-scan GC–MS after acid hydrolysis, liquid–liquid extraction,
and microwave-assisted acetylation allowed the detection of mCPP and its previously
mentioned metabolites in rat urine after single administration of a dose calculated
from the doses commonly taken by drug users. The hydroxy-mCPP metabolites should
be used as target analytes being the major metabolites of mCPP. Assuming similar
metabolism, our STA procedure should be suitable for detection of an intake
of mCPP in human urine. Furthermore, possibilities for differentiating an intake
of mCPP from that of its precursor drugs trazodone or nefazodone, two common
antidepressants, are described. Within the context of these studies, N-(3-chlorophenyl)ethylenediamine
was identified as a new metabolite of these two antidepressants. Reproduction
of editorial content of this journal is prohibited without publisher’s
permission.
This
article is available in its entirety by fax for $40.00 each.
Visa, MasterCard and AMEX accepted.
To
order electronically click here
or call: 847-647-2900 ext. 1323
or fax request to: 847-647-1155.
To order multiple copies click here.
Please indicate JAT
volume and issue along with page numbers. |
|
Home | Subscribe
| Current Issue | Back Issues
| Search | Advertise | Other Publications
| |
