l-(<i>m</i>-Chlorophenyl)piperazine: a metabolite of trazodone isolated from rat urine

Melzacka, M; Boksa, J.; J, Maj

doi:10.1111/j.2042-7158.1979.tb13680.x

Cited by 53 publications

(18 citation statements)

References 7 publications

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“…In contrast to the first study, small amounts of unmetabolized mCPP were detected in urine and hydroxy mCPP could also be found unconjugated. In studies on the mCPP precursor drug trazodone, the formation of mCPP N-glucuronides was reported [131,162].…”

Section: Metabolism Of Mcppmentioning

confidence: 98%

“…It is an active metabolite of therapeutics such as trazodone [129][130][131][132], nefazodone [132,133], etoperidone [129,[134][135][136], and mepiprazol [129]. mCPP has been found to interact with different serotonin receptors showing mainly nonselective agonistic properties, but antagonistic effects have been described as well [102,137,138].…”

Section: -(3-chlorophenyl)piperazine (Mcpp)mentioning

confidence: 99%

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Metabolism of Designer Drugs of Abuse

Staack

Maurer

2005

CDM

107

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Abuse of designer drugs is widespread among young people, especially in the so-called "dance club scene" or "rave scene", worldwide. Severe and even fatal poisonings have been attributed to the consumption of such drugs of abuse. However, in contrast to new medicaments, which are extensively studied in controlled clinical studies concerning metabolism, including cytochrome P450 isoenzyme differentiation, and further pharmacokinetics, designer drugs are consumed without any safety testing. This paper reviews the metabolism of new designer drugs of abuse that have emerged on the black market during the last years. Para-methoxyamphetamine (PMA), para-methoxymethamphetamine (PMMA) and 4-methylthioamphetamine (4-MTA), were taken into consideration as new "classical" amphetamine-derived designer drugs. Furthermore, N-benzylpiperazine (BZP), 1-(3, 4-methylenedioxybenzyl)piperazine (MDBP), 1-(3-trifluoromethylphenyl)piperazine (TFMPP), 1-(3-chlorophenyl)piperazine (mCPP) and 1-(4-methoxyphenyl)piperazine (MeOPP) were taken into consideration as derivatives of the class of piperazine-derived designer drugs, as well as alpha-pyr-rolidinopropiophenone (PPP), 4'-methoxy-alpha-pyrrolidinopropiophenone (MOPPP), 3', 4'-methylenedioxy-alpha-pyrrolidino-propiophenone (MDPPP), 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP), and 4'-methyl-alpha-pyrrolidinoexanophenone (MPHP) as derivatives of the class of alpha-pyrrolidinophenone-derived designer drugs. Papers describing identification of in vivo or in vitro human or animal metabolites and cytochrome P450 isoenzyme dependent metabolism have been considered and summarized.

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Section: Metabolism Of Mcppmentioning

confidence: 98%

Section: -(3-chlorophenyl)piperazine (Mcpp)mentioning

confidence: 99%

Metabolism of Designer Drugs of Abuse

Staack

Maurer

2005

CDM

107

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“…m-CPP, a metabolite of the antidepressant drug trazodone (Melzacka et al, 1979) markedly reduces food intake in rats (Samanin et al, 1979). This effect on food intake appears to result from postsynaptic 5-HT receptor stimulation since it is prevented by the 5-HT antagonist metergoline but not by mid-brain raphe lesions (Samanin et al, 1979).…”

Section: Introductionmentioning

confidence: 99%

Long‐term imipramine treatment enhances locomotor and food intake suppressant effects of m‐chlorophenylpiperazine in rats

Aulakh

Cohen

Hill

et al. 1987

British J Pharmacology

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1 Administration of the 5-HTIB receptor agonist m-chlorophenylpiperazine (m-CPP) to rats produces dose-dependent decreases in locomotor activity and food intake. 2 The locomotor suppressant effect of m-CPP was inhibited by the 5-hydroxytryptaminergic antagonist, metergoline, but not by phentolamine, propranolol, clonidine, or haloperidol. 4 The food intake suppressant effects of m-CPP were enhanced following both short (3-5 days) and longer-term (21 days) treatment with imipramine. Rapidly developing 5-hydroxytryptamine uptake inhibition may be responsible for this change, or it may represent an earlier adaptive change in the 5-HTIB receptors mediating food intake compared to more complexly modulated motor responses.

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“…The phenylpiperazine 1-(m-chlorophenyl)piperazine (mCPP) is the active metabolite of the psychotropic drugs trazodone, etoperidone and mepiprazole and may be (co)responsible for the psychotropic e¤ects of these compounds (Melzacka et al 1979;Caccia et al 1981;Fong et al 1982). mCPP binds to serotonergic (5-HT) receptors and is frequently used as a pharmacological probe to determine the status of brain 5-HT function in patients with neuropsychiatric disorders (Kahn and Wetzler 1991).…”

Section: Introductionmentioning

confidence: 99%

Discriminative stimulus properties of mCPP: evidence for a 5-HT 2C receptor mode of action

Gommans¹,

Hijzen²,

Maes

et al. 1998

Psychopharmacology

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Previous drug discrimination studies with the serotonergic drug m-chlorophenylpiperazine (mCPP) showed conflicting results, with some authors concluding that the cue was mediated by 5-HT2C receptors, but others that it was definitively not. We further examined the discriminative stimulus properties of mCPP in rats and reviewed previously published data. We trained rats to discriminate mCPP (2.0 mg/kg, PO) from water. We found that the mCPP cue generalized to m-trifluoromethyl-phenylpiperazine (TFMPP) and 6-chloro-2-(1-piperazinyl)-pyrazine (MK-212), and partially to eltoprazine, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI), fenfluramine and trazodone. A moderate level of generalization was obtained with quipazine, 1-(m-chlorophenyl)biguanide and clonidine. No generalization was found with flesinoxan, methiothepin, idazoxan and haloperidol. Mianserin and methysergide antagonized the mCPP stimulus, whereas ketanserin antagonized it partially. Metergoline, methiothepin and clozapine only marginally antagonized the mCPP stimulus. These results show that the discriminative stimulus effects of mCPP are predominantly mediated by 5-HT2C receptors, and to some extent by 5-HT1B receptors. When considering our results and other research together, the substitution tests clearly point to a 5-HT2C receptor mediated stimulus, with an additional role for 5-HT1B receptors. Antagonism studies are less clearcut, but are also suggestive of a 5-HT2C receptor mediated effect. A definitive answer as to whether other receptors, e.g. 5-HT2B and 5-HT7, are of any importance in mCPP's discriminative stimulus properties has to wait for more selective ligands.

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l-(m-Chlorophenyl)piperazine: a metabolite of trazodone isolated from rat urine

Cited by 53 publications

References 7 publications

Metabolism of Designer Drugs of Abuse

Metabolism of Designer Drugs of Abuse

Long‐term imipramine treatment enhances locomotor and food intake suppressant effects of m‐chlorophenylpiperazine in rats

Discriminative stimulus properties of mCPP: evidence for a 5-HT 2C receptor mode of action

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