Enantioselective metabolism of the designer drugs 3,4-methylenedioxymethamphetamine ('ecstasy') and 3,4-methylenedioxyethylamphetamine ('eve') isomers in rat brain and blood

Neuroscience Letters

Volumn 330, Issue 2, 2002, Pages 193-197

  Meyer, Anja ^a   Mayerhofer, Andreas ^a   Kovar, Karl Artur ^a   Schmidt, Werner J ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

3,4 Methylenedioxyethylamphetamine; 3,4 Methylenedioxymethamphetamine; Enantioselective; High performance liquid chromatography with fluorimetric detection; Metabolism; Solid phase extraction

Indexed keywords

3,4 METHYLENEDIOXYETHYLAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; AMPHETAMINE DERIVATIVE; NEUROTOXIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD ANALYSIS; BRAIN CORTEX; BRAIN HOMOGENATE; CONTROLLED STUDY; CORPUS STRIATUM; DRUG METABOLISM; ENANTIOSELECTIVITY; FLUOROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NONHUMAN; PRIORITY JOURNAL; RAT; SOLID PHASE EXTRACTION; URINALYSIS; VALIDATION PROCESS;

ANALYSIS OF VARIANCE; ANIMALS; BRAIN; BRAIN CHEMISTRY; CEREBRAL CORTEX; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CORPUS STRIATUM; DESIGNER DRUGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HALLUCINOGENS; INJECTIONS, SUBCUTANEOUS; ISOMERISM; N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE; RATS; RATS, SPRAGUE-DAWLEY; SEROTONIN AGENTS;

EID: 0037144199     PISSN: 03043940     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3940(02)00776-0     Document Type: Article

References (17)

1. International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use. Step 3: Guideline on Validation of Analytical Procedures: Methodology, ICH Secretary, Geneva, Switzerland, 1996.
2. Braun U., Shulgin A.T., Braun G. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). J. Pharm. Sci. 69:1980;192-195.
3. Brunnenberg M., Kovar K.A. Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. J. Chromatogr. B Biomed. Sci. Appl. 10:2001;9-18.
4. Ensslin H.K., Maurer H.H., Gouzoulis E., Hermle L., Kovar K.A. Metabolism of racemic 3,4-methylenedioxyethylamphetamine in humans. Isolation, identification, quantification, and synthesis of urinary metabolites. Drug Metab. Dispos. 24:1996;813-820.
5. Fallon J.K., Kicman A.T., Henry J.A., Milligan P.J., Cowan D.A., Hutt A.J. Stereospecific analysis and enantiomeric disposition of 3,4-methylenedioxymethamphetamine (Ecstasy) in humans. Clin. Chem. 45:1999;1058-1069.
6. Hermle L., Spitzer M., Borchardt D., Kovar K., Gouzoulis E. Psychological effects of MDE in normal subjects. Are entactogens a new class of psychoactive agents? Neuropsychopharmacology. 8:1993;171-176.
7. Johnson M., Elayan I., Hanson G., Foltz R., Gibb J., Lim H. Effects of 3,4-dihydroxymethamphetamine and 2,4,5-trihydroxymethamphetamine, two metabolites of 3,4-methylenedioxymethamphetamine, on central serotonergic and dopaminergic systems. J. Pharmacol. Exp. Ther. 261:1992;447-453.
8. Kreth K., Kovar K., Schwab M., Zanger U. Identification of the human cytochromes P450 involved in the oxidative metabolism of "Ecstasy"-related designer drugs. Biochem. Pharmacol. 15:2000;1563-1571.
9. Lim H.K., Su Z., Foltz R.L. Stereoselective disposition: enantioselective quantitation of 3,4-(methylenedioxy) methamphetamine and three of its metabolites by gas chromatography/electron capture negative ion chemical ionization mass spectrometry. Biol. Mass Spectrom. 22:1993;403-411.
10. Maurer H., Bickeboeller-Friedrich J., Kraemer T., Peters F. Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy'). Toxicol. Lett. 112-113:2000;133-142.
11. Morgan M.J. Ecstasy (MDMA): a review of its possible persistent psychological effects. Psychopharmacology. 152:2000;230-248.
12. Nichols D.E. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: entactogens. J. Psychoact. Drugs. 18:1986;305-313.
13. Ricaurte G., Yuan J., McCann U.D. 3,4-Methylenedioxymethymphetamine ("ecstasy")-induced serotonin neurotoxicity: studies in animals. Neuropsychobiology. 42:2000;5-10.
14. Ricaurte G.A., Finnegan K.F., Nichols D.E., DeLanney L.E., Irwin I., Langston J.W. 3,4-Methylenedioxyethylamphetamine (MDE), a novel analogue of MDMA, produces long-lasting depletion of serotonin in the rat brain. Eur. J. Pharmacol. 137:1987;265-268.
15. Schmidt C. Neurotoxicity of the psychedelic amphetamine, methylenedioxymethamphetamine. J. Pharmacol. Exp. Ther. 240:1987;1-7.
16. Spitzer M., Franke B., Walter H., Buechler J., Wunderlich A.P., Schwab M., Kovar K.A., Hermle L., Gron G. Enantio-selective cognitive and brain activation effects of N-ethyl-3,4-methylenedioxyamphetamine in humans. Neuropharmacology. 41:2001;263-271.
17. Tedeschi L., Frison G., Castasgna F., Giorgetti R., Ferrara S.D. Simultaneous identification of amphetamine and its derivatives in urine using HPLC-UV. Int. J. Leg. Med. 105:1993;265-269.