Chemistry, Pharmacology, Toxicology, and Hepatic Metabolism of Designer Drugs of the Amphetamine (Ecstasy), Piperazine, and Pyrrolidinophenone Types
Hans H Maurer, Thomas Kræmer, Dietmar Springer, Roland F. Staack
Therapeutic Drug Monitoring March 19, 2004 DOI: 10.1097/00007691-200404000-00007 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Review Peer reviewed |
|---|---|
| Topics | MDMA Mescaline |
| Keywords | Designer drug Euphoriant Pharmacology Amphetamine Hallucinogen Piperazine |
| Citations | 147 |
| Key findings | CYP2D6 is the major enzyme catalyzing the main metabolic steps of piperazine- and pyrrolidinophenone-derived designer drugs, but the clinical relevance of its genetic polymorphism is unknown. |
Abstract
Designer drugs of the amphetamine type (eg, MDMA, MDEA, MDA), of the new benzyl or phenyl piperazine type (eg, BZP, MDBP, mCPP, TFMPP, MeOPP), or of the pyrrolidinophenone type (eg, PPP, MOPPP, MDPPP, MPPP, MPHP) have gained popularity and notoriety as rave drugs. These drugs produce feelings of euphoria and energy and a desire to socialize. Although in the corresponding drug scene designer drugs have the reputation of being safe, studies in rats and primates in combination with human epidemiologic investigations indicate potential risks to humans. Thus, a variety of adverse effects have been associated with the use/abuse of this class of drugs in humans, including a life-threatening serotonin syndrome, hepatotoxicity, neurotoxicity, and psychopathology. Metabolites were suspected to contribute to some of the toxic effects. Therefore, knowledge of the metabolism is a prerequisite for toxicologic risk assessment. The metabolic pathways, the involvement of cytochrome P450 isoenzymes in the main pathways, and their roles in hepatic clearance are described for designer drugs of different groups. In summary, polymorphically expressed CYP2D6 was the major enzyme catalyzing the major metabolic steps of the studied piperazine- and pyrrolidinophenone-derived designer drugs. However, it cannot be concluded at the moment whether this genetic polymorphism is of clinical relevance.
Comparable studies
Other narrative reviews on MDMA, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Human Pharmacology of MDMA | 2004 | Review | |
| Human psychopharmacology of Ecstasy (MDMA): a review of 15 years of empirical research | 2001 | Review | |
| 3,4‐Methylenedioxymethamphetamine (MDMA, “Ecstasy”): pharmacology and toxicology in animals and humans | 1994 | Review | |
| (±)3,4-Methylenedioxymethamphetamine (‘Ecstasy’)-Induced Serotonin Neurotoxicity: Studies in Animals | 2000 | Review | |
| Amphetamine toxicities | 2010 | Review |
Citations in the library
Cited by 9
- Instability of the ecstasy market and a new kid on the block: mephedrone Journal of Psychopharmacology September 8, 2010
- Metabolism of designer drugs of abuse: an updated review. Current Drug Metabolism June 1, 2010
- Qualitative Research of Online Drug Misuse Communities with Reference to the Novel Psychoactive Substances University of Hertfordshire Research Archive May 29, 2013
- Benzylpiperazine: "A messy drug". Drug and Alcohol Dependence July 1, 2016
- Linking the pharmacological content of ecstasy tablets to the subjective experiences of drug users. Psychopharmacology April 2012
and 4 more in the library
Cites 8
- Positron emission tomographic evidence of toxic effect of MDMA (“Ecstasy”) on brain serotonin neurons in human beings The Lancet October 1, 1998
- Toxicokinetics of Amphetamines: Metabolism and Toxicokinetic Data of Designer Drugs, Amphetamine, Methamphetamine, and Their N-Alkyl Derivatives Therapeutic Drug Monitoring April 1, 2002
- Fatal multi-organ failure after suicidal overdose with MDMA, `Ecstasy': case report and review of the literature Human & Experimental Toxicology February 1, 1999
- 3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy) and Driving Impairment Journal of Forensic Sciences November 1, 2001
- Identification of the human cytochromes P450 involved in the oxidative metabolism of "Ecstasy"-related designer drugs. Biochemical Pharmacology June 15, 2000
and 3 more in the library