Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters

Journal of Pharmacology and Experimental Therapeutics

Volumn 314, Issue 1, 2005, Pages 346-354

  Pifl, Christian ^a   Nagy, Gabor ^b   Berényi, Sándor ^c   Kattinger, Alexandra ^a   Reither, Harald ^a   Antus, Sándor ^c  

^a Medical University of Vienna   (Austria)

^b UNIVERSITY OF SZEGED   (Hungary)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; 1,3 BIS(3,4 METHYLENEDIOXYPHENYL) 2 PROPANAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; ACETAMIDE; AMINE; CARRIER PROTEIN; COMPLEMENTARY DNA; DOPAMINE TRANSPORTER; FORMAMIDE; MONOAMINE; N FORMYL 1,3 BIS(3,4 METHYLENEDIOXYPHENYL)PROP 2 YL AMINE; NITRO DERIVATIVE; NORADRENALIN TRANSPORTER; PHENYL GROUP; RECOMBINANT PROTEIN; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CORRELATION ANALYSIS; EMBRYO; EMBRYO CELL; EXPERIMENT; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IC 50; INHIBITION KINETICS; KIDNEY CELL; METABOLISM; NEUROBLASTOMA; NEUROTOXICITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN SECRETION; STRUCTURE ACTIVITY RELATION;

BIOGENIC MONOAMINES; CARRIER PROTEINS; CELL LINE; CLOMIPRAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; DOPAMINE UPTAKE INHIBITORS; HALLUCINOGENS; HUMANS; INDICATORS AND REAGENTS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MAZINDOL; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE; NERVE TISSUE PROTEINS; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; RECOMBINANT PROTEINS; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SYMPORTERS;

EID: 23044494989     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.105.084426     Document Type: Article

References (44)

1. Appell M, Berfield JL, Wang LC, Dunn WJ III, Chen N, and Reith ME (2004) Structure-activity relationships for substrate recognition by the human dopamine transporter. Biochem Pharmacol 67:293-302.
2. Barker EL, Kimmel HL, and Blakely RD (1994) Chimeric human and rat serotonin transporters reveal domains involved in recognition of transporter ligands. Mol Pharmacol 46:799-807.
3. Battaglia G, Yeh SY, O'Hearn E, Molliver ME, Kuhar MJ, and De Souza EB (1987) 3,4-Methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine destroy serotonin terminals in rat brain: quantification of neurodegeneration by measurement of [3H]paroxetine-labeled serotonin uptake sites. J Pharmacol Exp Ther 242:911-916.
4. Baumann MH, Ayestas MA, Dersch CM, and Rothman RB (2001) 1-(m-Chlorophenyl) piperazine (mCPP) dissociates in vivo serotonin release from long-term serotonin depletion in rat brain. Neuropsychopharmacology 24:492-501.
5. Benington F, Morin RD, Clark L, and Fox RP (1958) Psychopharmacological activity of ring- and side chain-substituted β-phenethylamines. J Org Chem 23:1979-1983.
6. Bohn M, Bohn G, and Blaschke G (1993) Synthesis markers in illegally manufactured 3,4-methylenedioxyamphetamine and 3,4- methylenedioxymethamphetamine. Int J Leg Med 106:19-23.
7. Braun U, Shulgin T, and Braun G (1980) Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4- methylenedioxyamphetamine). J Pharm Sci 69:192-195.
8. Burgen ASV and Iversen LL (1965) The inhibition of noradrenaline uptake by sympathomimetic amines in the rat isolated heart. Brit J Pharmacol Chemother 25:34-49.
9. Fischer C, Hatzidimitriou G, Wlos J, Katz J, and Ricaurte G (1995) Reorganization of ascending 5-HT axon projections in animals previously exposed to the recreational drug (+/-)3,4-methylenedioxymethamphetamine (MDMA, "ecstasy"). J Neurosci 15:5476-5485.
10. Fischer JF and Cho AK (1979) Chemical release of dopamine from striatal homogenates: evidence for an exchange diffusion model. J Pharmacol Exp Ther 208:203-209.
11. Fitzgerald JL and Reid JJ (1990) Effects of methylenedioxymethamphetamine on the release of monoamines from rat brain slices. Eur J Pharmacol 191:217-220.
12. Giros B, el Mestikawy S, Godinot N, Zheng K, Han H, Yang-Feng T, and Caron MG (1992) Cloning, pharmacological characterization and chromosome assignment of the human dopamine transporter. Mol Pharmacol 42:383-390.
13. Gough B, Ali SF, Slikker W Jr, and Holson RR (1991) Acute effects of 3,4-methylenedioxymethamphetamine (MDMA) on monoamines in rat caudate. Pharmacol Biochem Behav 39:619-623.
14. Green AR, Mechan AO, Elliott JM, O'Shea E, and Colado MI (2003) The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy"). Pharmacol Rev 55:463-508.
15. Herbst RM and Manske RH (1947) Methylbenzyl ketone from phenylacetic acid. Org Synt Coll Vol 2:389-391.
16. Horn AS (1973) Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br J Pharmacol 47:332-338.
17. Johnson MP, Hoffman AJ, and Nichols DE (1986) Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur J Pharmacol 132:269-276.
18. Kalant H (2001) The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs. CMAJ 165:917-928.
19. Kodukulla RPK, Trivedi GK, Vora D, and Mathur HH (1994) Synthesis, chemical transformation and antimicrobial activity of a novel class of nitroolefins: 1,3-diariyl-2-nitroprop-1-enes. Synth Commun 24:819-832.
20. Langston JW (1985) MPTP and Parkinson's disease. Trends Neurosci 8:79-83.
21. Liechti ME, Baumann C, Gamma A, and Vollenweider FX (2000) Acute psychological effects of 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") are attenuated by the serotonin uptake inhibitor citalopram. Neuropsychopharmacology 22:513-521.
22. Lukaszewski T (1982) Spectroscopic and chromatographic identification of precursors, intermediates and impurities of 3,4-methylenedioxyamphetamine synthesis. J Assoc Off Anal Chem 61:951-967.
23. Malberg JE, Sabol KE, and Seiden LS (1996) Co-administration of MDMA with drugs that protect against MDMA neurotoxicity produces different effects on body temperature in the rat. J Pharmacol Exp Ther 278:258-267.
24. Meiergerd SM and Schenk JO (1994) Striatal transporter for dopamine: catechol structure-activity studies and susceptibility to chemical modification. J Neurochem 62:998-1008.
25. Nichols DE, Hoffman AJ, Oberlender RA, Jacob P 3rd, and Shulgin AT (1986) Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class. J Med Chem 29:2009-2015.
26. Noggle FT, Clark CR, and De Ruiter J (1991) Gas chromatographic and mass spectrometric analysis of samples from clandestine laboratories involved in the synthesis of ecstasy from sassafras oil. J Chrom Sci 29:168-173.
27. Paczkowski FA, Bryan-Lluka LJ, Pörzgen P, Brüss M, and Bönisch H (1999) Comparison of the pharmacological properties of cloned rat, human and bovine norepinephrine transporters. J Pharmacol Exp Ther 290:761-767.
28. Palhol F, Boyer S, Naulet N, and Chabrillat M (2002) Impurity profiling of seized MDMA tablets by capillary gas chromatography. Anal Bioanal Chem 374:274-281.
29. Pearl JA and Beyer DL (1951) Reactions of vanillin and its derived compounds: XII. Benzyl methyl ketones derived from vanillin and its related compounds. J Org Chem 16:221-224.
30. Pifl C, Drobny H, Reither H, Hornykiewicz O, and Singer EA (1995) Mechanism of the dopamine-releasing actions of amphetamine and cocaine: plasmalemmal dopamine transporter versus vesicular monoamine transporter. Mol Pharmacol 47:368-373.
31. Pifl C, Hornykiewicz O, Giros B, and Caron MG (1996) Catecholamine transporters and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine neurotoxicity: studies comparing the cloned human noradrenaline and human dopamine transporter. J Pharmacol Exp Ther 277:1437-1443.
32. Renton RJ, Cowie JS, and Oon MCH (1993) A study of the precursors, intermediates and reaction by-products in the synthesis of 3,4- methylenedioxymethylamphetamine and its application to forensic drug analysis. Forensic Sci Int 60:189-202.
33. Ricaurte GA, Forno LS, Wilson MA, DeLanney LE, Irwin I, Molliver ME, and Langston JW (1988) (+/-)3,4-methylenedioxymethamphetamine selectively damages central serotonergic neurons in nonhuman primates. J Am Med Assoc 260:51-55.
34. Ricaurte GA, Martello AL, Katz JL, and Martello MB (1992) Lasting effects of (+-)-3,4-methylenedioxymethamphetamine (MDMA) on central serotonergic neurons in nonhuman primates: neurochemical observations. J Pharmacol Exp Ther 261:616-622.
35. Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, and Partilla JS (2001) Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse 39:32-41.
36. Sanchez V, Camarero J, Esteban B, Peter MJ, Green AR, and Colado MI (2001) The mechanisms involved in the long-lasting neuroprotective effect of fluoxetine against MDMA ("ecstasy")-induced degeneration of 5-HT nerve endings in rat brain. Br J Pharmacol 134:46-57.
37. Schmidt CJ (1987) Neurotoxicity of the psychedelic amphetamine, methylenedioxymethamphetamine. J Pharmacol Exp Ther 240:1-7.
38. Schmidt CJ, Levin JA, and Lovenberg W (1987) In vitro and in vivo neurochemical effects of methylenedioxymethamphetamine on striatal monoaminergic systems in the rat brain. Biochem Pharmacol 36:747-755.
39. Scholze P, Zwach J, Kattinger A, Pifl C, Singer EA, and Sitte HH (2000) Transportermediated release: a superfusion study on human embryonic kidney cells stably expressing the human serotonin transporter. J Pharmacol Exp Ther 293:870-878.
40. Shankaran M, Yamamoto BK, and Gudelsky GA (1999) Mazindol attenuates the 3,4-methylenedioxymethamphetamine-induced formation of hydroxyl radicals and long-term depletion of serotonin in the striatum. J Neurochem 72:2516-2522.
41. Stein DJ and Rink J (1999) Effects of "Ecstasy" blocked by serotonin reuptake inhibitors. J Clin Psychiatry 60:485.
42. Wall SC, Gu H, and Rudnick G (1995) Biogenic amine flux mediated by cloned transporters stably expressed in cultured cell lines: amphetamine specificity for inhibition and efflux. Mol Pharmacol 47:544-550.
43. Wichems CH, Hollingsworth CK, and Bennett BA (1995) Release of serotonin induced by 3,4-methylenedioxymethamphetamine (MDMA) and other substituted amphetamines in cultured fetal raphe neurons: further evidence for calciumindependent mechanisms of release. Brain Res 695:10-18.
44. Yamamoto BK and Spanos LJ (1988) The acute effects of methylenedioxymethamphetamine on dopamine release in the awake-behaving rat. Eur J Pharmacol 148:195-203.