Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs (‘Ecstasy’)

Maurer, Hans H.; Bickeboeller-Friedrich, Joerg; Kræmer, Thomas; Peters, Frank T.

doi:10.1016/s0378-4274(99)00207-6

Cited by 181 publications

(156 citation statements)

References 26 publications

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“…A substantial amount is known about MDMA absorption, distribution, and elimination in mature animals and humans [37,87]. At least fourteen metabolites are produced in vivo from MDMA [58].…”

Section: Pharmacokineticsmentioning

confidence: 99%

A developmental comparison of the neurobehavioral effects of ecstasy (MDMA)

Piper

2007

Neurotoxicology and Teratology

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The entactogen ±3,4-methylenedioxymethamphetamine (MDMA or ecstasy) is a popular recreational drug among college, high school, and, occasionally, middle school students. Preclinical research examining the acute and long-term effects of MDMA has predominately been conducted in reproductively mature subjects but there has been increasing interest in adolescent and in utero exposure. This review examines the acute and long-term responses to MDMA during perinatal, adolescent, and adult periods. The ability of MDMA to alter core body temperature emerges gradually during ontogeny while a reduction in body weight is evident at all ages. Learning and workingmemory are also altered independent of the developmental stage of exposure. Current evidence suggests adults are more sensitive to the long-term serotonin depletions following MDMA but younger ages also exhibit substantial and rapid neuroplasticity. Sexually dimorphic MDMA responses have been identified for the acute hyperthermic and motoric effects of MDMA with pubescent males being especially susceptible. Several physiological, behavioral, and neurochemical MDMA issues requiring further study are also outlined. Keywords±3; 4-methylenedioxymethamphetamine; Adolescence; Anxiety; Depression; Learning; SerotoninThe phenylethylamine ±3,4-methylenedioxymethamphetamine (MDMA) is a popular recreational drug best known as ecstasy. MDMA has several other street names including Adam, baby slits, chocolate chips, clarity, doctor, essence, kleenex, and roll [77]. Although ecstasy has some similarities with both stimulants and hallucinogens, MDMA is an entactogen. Entactogen means "touching within" based on the drug's subjective effects [110]. MDMA also causes long term changes in several markers of the integrity of the serotonin (5-HT) neurotransmitter system [58]. There have been several excellent recent reviews on MDMA toxicology, pharmacokinetics, pharmacodynamics, and neurobehavioral consequences [30,37,113,157], but none have systematically addressed the intricate effects of MDMA during development.Ecstasy use is not restricted to limited subpopulations, that is fans of techno music and "raves" [173] or male homosexuals [73,81], as MDMA has expanded into the general population [124,148,170] and especially young people [52,78,170,172]. Over one hundred pregnant women in Toronto called a substance abuse helpline between 1998 and 2000 to inquire Corresponding Author: Brian J. Piper, Neuroscience and Behavior Program, University of Massachusetts, Amherst, MA 01003-7710, Tel: (413) 545-0996, bpiper@nsm.umass.edu Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers...

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“…A substantial amount is known about MDMA absorption, distribution, and elimination in mature animals and humans [37,87]. At least fourteen metabolites are produced in vivo from MDMA [58].…”

Section: Pharmacokineticsmentioning

confidence: 99%

A developmental comparison of the neurobehavioral effects of ecstasy (MDMA)

Piper

2007

Neurotoxicology and Teratology

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“…HMMA can be further conjugated by UDP-glucuronyltransferases or by sulfotransferases. A minor pathway includes demethylation to 3,4-methylendioxyamphetamine (MDA) followed by demethylenation to 3,4-dihydroxyamphetamine, O-methylation to 4-hydroxy-3-methoxyamphetamine (HMA) and conjugation [17][18][19]. In urine samples of recreational MDMA users following a controlled single dose of MDMA, DHMA 3-sulfate, HMMA 4-sulfate and HMMA 4-glucuronide were detected as major metabolites next to unchanged MDMA [20].…”

Section: Introductionmentioning

confidence: 99%

Development and validation of an LC‐MS/MS method after chiral derivatization for the simultaneous stereoselective determination of methylenedioxy‐methamphetamine (MDMA) and its phase I and II metabolites in human blood plasma

Steuer

Schmidhauser

Liechti

et al. 2014

Drug Testing and Analysis

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This is the peer reviewed version of the following article: Steuer, A. E., Schmidhauser, C., Liechti, M. E., and Kraemer, T. (2015), Development and validation of an LC-MS/MS method after chiral derivatization for the simultaneous stereoselective determination of methylenedioxy-methamphetamine (MDMA) and its phase I and II metabolites in human blood plasma. Drug Test. Analysis, 7, 592-602, which has been published in final form at http://dx.doi.org/10.1002/dta.1740. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. resulting in the formation of diastereomers which were easily separable on standard reverse phase stationary phases. This simple and fast method was validated according to international guidelines including specificity, recovery, matrix effects, accuracy and precision, stabilities, and limits of quantification. The method proved to be selective, sensitive, accurate and precise for all tested analytes except for DHMA. The method was applied to the analysis of more than 400 samples from a controlled study after application of MDMA.

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“…Besides the putative analytical interest, the results thus gathered can hopefully help to clarify the hypothetical in vivo N-demethylation oxidation process. Actually, MDMA metabolism is known to comprise one or more oxidative pathways [13].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

Milhazes

Martins

Uriarte

et al. 2007

Analytica Chimica Acta

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A complete physicochemical characterisation of MDMA and its synthetic precursors MDA, 3,4-methylenedioxybenzaldehyde (piperonal) and 3,4-methylenedioxy-␤-methyl-␤-nitrostyrene was carried out through voltammetric assays and Raman spectroscopy combined with theoretical (DFT) calculations. The former provided important analytical redox data, concluding that the oxidative mechanism of the N-demethylation of MDMA involves the removal of an electron from the amino-nitrogen atom, leading to the formation of a primary amine and an aldehyde. The vibrational spectroscopic experiments enable to afford a rapid and reliable detection of this type of compounds, since they yield characteristic spectral patterns that lead to an unequivocal identification.Moreover, the rational synthesis of the drug of abuse 3,4-methylenedioxymethamphetamine (MDMA or "ecstasy") from one of its most relevant precursors 3,4-methylene-dioxyamphetamine (MDA), is reported. In addition, several approaches for the N-methylation of MDA, a limiting synthetic step, were attempted and the overall yields compared.

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Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs (‘Ecstasy’)

Cited by 181 publications

References 26 publications

A developmental comparison of the neurobehavioral effects of ecstasy (MDMA)

A developmental comparison of the neurobehavioral effects of ecstasy (MDMA)

Development and validation of an LC‐MS/MS method after chiral derivatization for the simultaneous stereoselective determination of methylenedioxy‐methamphetamine (MDMA) and its phase I and II metabolites in human blood plasma

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

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