"deconstruction" of the abused synthetic cathinone methylenedioxypyrovalerone (MDPV) and an examination of effects at the human dopamine transporter

ACS Chemical Neuroscience

Volumn 4, Issue 12, 2013, Pages 1524-1529

  Kolanos, Renata ^a   Solis, Ernesto ^a   Sakloth, Farhana ^a   De Felice, Louis J ^a   Glennon, Richard A ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

"bath salts"; keto amphetamines; ketophenylalkylamines; bk Amphetamines; drug abuse; electrophysiology; hDAT

Indexed keywords

ALKYL GROUP; CARBONYL DERIVATIVE; CATHINONE; DOPAMINE TRANSPORTER; METHYLENEDIOXYPYROVALERONE; PYROVALERONE; TERTIARY AMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL STRAIN HEK293; DRUG ABUSE; EMBRYO; FEMALE; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; IC 50; MAMMAL CELL; NONHUMAN; OOCYTE; PRIORITY JOURNAL; VOLTAGE CLAMP TECHNIQUE; XENOPUS LAEVIS;

ANIMALS; BENZODIOXOLES; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; HEK293 CELLS; HUMANS; PATCH-CLAMP TECHNIQUES; PYRROLIDINES; TRANSFECTION; XENOPUS;

EID: 84890693905     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn4001236     Document Type: Article

References (35)

1. United Nations Narcotic Laboratory Document. ((1975) Studies on the chemical composition of khat. III. Investigations on the phenylalkylamine fraction. MNAR/11/75, GE.75-12624. United Nations, Geneva.
2. United Nations Narcotic Laboratory Document. ((1974) Studies on the chemical composition of khat. I. Extraction, screening investigations and solvent separation of khat components. MNAR/12/74, GE.74-12580. United Nations, Geneva.
3. Glennon, R. A., Yousif, M., Naiman, N. A., and Kalix, P. (1987) Methcathinone: A new and potent amphetamine-like agent Pharmacol., Biochem. Behav. 26, 547-551
4. Savenko, V. G., Semkin, E. P., Sorokin, V. I., and Kazankov, S. P. (1989) Expert examination of narcotic substances obtained from ephedrine. USSR Ministry of the Interior All-Union Scientific Research Institute Report, Moscow, pp 1-22.
5. Jacob, P. and Shulgin, A. T. (1996) Novel N-substituted 2-amino-3′,4′-methylene-dioxypropiophenones. WO Patent 9639133, December 12, 1996.
6. Dal Cason, T. A., Young, R., and Glennon, R. A. (1997) Cathinone: An investigation of several N -alkyl and methylenedioxy analogs Pharmacol., Biochem. Behav. 58, 1109-1116
7. Iversen, L. E. (2010) Consideration of the cathinones. Advisory Council on the Misuse of Drugs. A report submitted to the Home Secretary of the UK (March 31, 2010).
8. Spiller, H. A., Ryan, M. L., Weston, R. G., and Jansen, J. (2011) Clinical experience with analytical confirmation of "bath salts" and "legal highs" (synthetic cathinones) in the United States Clin. Toxicol. 49, 499-505
9. Boehringer Ingelheim. ((1969) α-Substituted-ketones and processes for their preparation. British Patent 1,149,366, April 23, 1969.
10. Fuwa, T., Fukumori, N., Tanaka, T., Kubo, Y., Ogata, A., Uehara, S., Honda, Y., and Kodama, T. (2007) Microdialysis study of drug effects on central nervous system: Changes of dopamine levels in mice striatum after oral administration of methylenedioxypyrovalerone Ann. Rep. Tokyo Metrop. Inst. Public Health 58, 287-292
11. Federal Register. ((2011) Schedules of Controlled Substances: Temporary placement of three synthetic cathinones into Schedule I. Federal Register (October 21, 2011), 76, 65371-65375.
12. Synthetic Drug Abuse Prevention Act. ((2012) Section 1152. Addition of synthetic drugs to Schedule I of the Controlled Substances Act, pp 138-140 (enacted January 3, 2012; signed July 9, 2012) [ http://www.gpo.gov/fdsys/pkg/ BILLS-112s3187enr/pdf/BILLS-112s3187enr.pdf ].
13. Federal Register. ((2013) Schedules of Controlled Substances: Placement of methylone into Schedule I. Federal Register (April 12, 2013), 78, 21818-21825.
14. Marusich, J. A., Grant, K. R., Blough, B. E., and Wiley, J. L. (2012) Effects of synthetic cathinones contained in "bath salts" on motor behavior and a functional observational battery in mice Neurotoxicology 33, 1305-1313
15. Fantegrossi, W. E., Gannon, B. M., Zimmerman, S. M., and Rice, K. C. (2013) In vivo effects of abused "bath salt" constituent 3,4-methylenedioxypyrovalerone (MDPV) in mice: Drug discrimination, thermoregulation, and locomotor activity Neuropsychopharmacology 38, 563-573
16. The challenge of new psychoactive substances. (2013) United Nations Office of Drugs and Crime. A United Nations Publication, Vienna, Austria.
17. Kalix, P. and Glennon, R. A. (1986) Further evidence for an amphetamine-like mechanism of action of the alkaloid cathinone Biochem. Pharmacol. 35, 3015-3019
18. Kolanos, R., Cameron, K. N., Vekariya, R. H., De Felice, L. J., and Glennon, R. A. (2011) "Bath salts": An imitation of methamphetamine plus cocaine? Southeast Regional Meeting of American Chemical Society (SERMACS), Richmond, VA, October 26-29.
19. Cameron, K., Kolanos, R., Verkariya, R., De Felice, L., and Glennon, R. A. (2013a) Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of "bath salts," produce opposite effects at the human dopamine transporter Psychopharmacology 227, 493-499
20. Cameron, K. N., Kolanos, R., Solis, E., Glennon, R. A., and De Felice, L. J. (2013b) Bath salts components mephedrone and methylenedioxypyrovalerone (MDPV) act synergistically at the human dopamine transporter Br. J. Pharmacol. 68, 1750-1757
21. Baumann, M. H., Ayestas, M. A., Partilla, J. S., Sink, J. R., Shulgin, A. T., Daley, P. F., Brandt, S. D., Rothman, R. B., Ruoho, A. E., and Cozzi, N. V. (2012) The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue Neuropsychopharmacology 37, 1192-1203
22. Baumann, M. H., Partilla, J. S., Lehner, K. R., Thorndike, E. B., Hoffman, A. F., Holy, M., Rothman, R. B., Goldberg, S. R., Lupica, C. R., Sitte, H. H., Brandt, S. D., Tella, S. R., Cozzi, N. V., and Schindler, C. W. (2013) Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive "bath salts" products Neuropsychopharmacology 1-11
23. Simmler, L. D., Buser, T. A., Donzelli, M., Schramm, Y., Diue, L. H., Huwyler, J., Chaboz, S., Hoener, M. C., and Liechti, M. E. (2013) Pharmacological characterization of designer cathinones in vitro Br. J. Pharmacol. 168, 458-470
24. Eshleman, A. J., Wolfrum, K. M., Hatfield, M. G., Johnson, R. A., Murphy, K. V., and Janowsky, A. (2013) Substituted methcathinones differ in transporter and receptor interactions Biochem. Pharmacol. 85, 1803-1815
25. Meltzer, P. C., Butler, D., Deschamps, J. R., and Madras, B. K. (2006) 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogues: A promising class of monoamine uptake inhibitors J. Med. Chem. 49, 1420-1432
26. Köppe, H., Ludwig, G., and Zeile, K. (1969) 1-(3′,4′- Methylenedioxy-phenyl)-2-pyrrolidino-alkanones-(1). US Patent 3478050, November 11, 1969.
27. Koppë, H., Ludwig, G., and Zeile, K. (1967) Verfahren zur Herstellung von substituierten Phenyl-alpha-aminoketonen und deren Saeureadditionssalzen bzw. deren optischen Antipoden. German Patent DE 1242241, June 15, 1967.
28. Boehringer Ingelheim G.M.B.H. (1967) Aryl-α- aminoketone derivatives. British Patent GB1085135, September 27, 1967.
29. Iwao, J. and Samejima, M. (1954) Alkanolamines. I. Syntheses of N-methyl-3,4-dihydroxyephedrine hydrochloride and its derivatives Yakugaku Zasshi 74, 548-50
30. Masazumi, T., Masaki, S., and Setsuo, Y. (1985) 1-Propanone Derivatives and Pharmaceutical Compositions Containing Same. Eur. Pat. Appl. 0163537, May 30, 1985.
31. Yamauchi, S. and Taniguchi, E. (1992) Synthesis and insecticidal activity of sesquilignan analogues with 2-alkyl-6-methoxy-3-(3, 4-methylenedioxyphenyl)- 1,4-benzodioxanyl group Biosci. Biotech. Biochem. 56, 1751-1759
32. -, and pH dependence of the human choline transporter (hCHT) in Xenopus oocytes: The proton inactivation hypothesis of hCHT in synaptic vesicles J. Neurosci. 26, 9851-9859
33. Ramsey, S. and De Felice, L. J. (2002) Serotonin transporter function and pharmacology are sensitive to expression level: evidence for an endogenous regulatory factor J. Biol. Chem. 277, 14475-14482
34. Machaca, K. and Hartzell, H. (1998) Assymetric distribution of Ca-activated Cl channels in Xenopus oocytes Biophys. J. 74, 1286-1295
35. Wang, H. W., Li, C. Z., Yang, Z. F., Zheng, Y. Q., Zhang, Y., and Liu, Y. M. (2006) Electrophysiological effect of fluoxetine on Xenopus oocytes heterologously expressing human serotonin transporter Acta Pharmacol. Sin. 27, 289-293