Stereoselective actions of methylenedioxypyrovalerone (MDPV) to inhibit dopamine and norepinephrine transporters and facilitate intracranial self-stimulation in rats

ACS Chemical Neuroscience

Volumn 6, Issue 5, 2015, Pages 771-777

  Kolanos, R ^a   Partilla, J S ^b   Baumann, M H ^b   Hutsell, B A ^a   Banks, M L ^a   Negus, S S ^a   Glennon, R A ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

cocaine; DAT; drug abuse; ICSS (intracranial self stimulation); MDPV; NET; psychomotor stimulants; reuptake inhibition; Synthetic cathinones

Indexed keywords

1 (BENZO[D][1,3]DIOXOL 5 YL) 2 (PYRROLIDIN 1 YL)PENTAN 1 OL HYDROCHLORIDE; 2 AMINO 1 (BENZO[D][1,3]DIOXOL 5 YL)PENTAN 1 OL HYDROCHLORIDE; 2 AMINO 1 (BENZO[D][1,3]DIOXOL 5 YL)PENTAN 1 ONE HYDROCHLORIDE; CENTRAL STIMULANT AGENT; COCAINE; DOPAMINE; DOPAMINE TRANSPORTER; METHYLENDIOXYPYROVALERONE HYDROCHLORIDE; METHYLENEDIOXYPYROVALERONE; N BOC LEVO NORVALINE; NORADRENALIN; NORADRENALIN TRANSPORTER; SEROTONIN; TERT BUTYL[1 (BENZO[D][1,3]DIOXOL 5 YL) 1 OXOPENTAN 2 YL]CARBAMATE; TERT BUTYL[1 OXO 1 (PYRROLIDIN 1 YL)PENTAN 2 YL]CARBAMATE; UNCLASSIFIED DRUG; 1,3 BENZODIOXOLE DERIVATIVE; 3,4-METHYLENEDIOXYPYROVALERONE; DESIGNER DRUG; PYRROLIDINE DERIVATIVE;

ADULT; ALKYLATION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN DEPTH STIMULATION; CRYSTALLIZATION; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; FACILITATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IC50; ISOMER; MALE; MEDIAL FOREBRAIN BUNDLE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; RAT; SELF STIMULATION; STEREOCHEMISTRY; ANIMAL; ANTAGONISTS AND INHIBITORS; BRAIN; CHEMISTRY; DRUG EFFECTS; SPRAGUE DAWLEY RAT; STEREOISOMERISM;

MUSCOVY DUCK PARVOVIRUS; RATTUS;

ANIMALS; BENZODIOXOLES; BRAIN; DESIGNER DRUGS; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; MALE; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; PYRROLIDINES; RATS; RATS, SPRAGUE-DAWLEY; SELF STIMULATION; STEREOISOMERISM;

EID: 84930198838     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/acschemneuro.5b00006     Document Type: Article

References (18)

1. United Nations Narcotic Laboratory. ((1975) Studies on the chemical composition of khat. III. Investigations on the phenylalkylamine fraction, MNAR/11/75, GE.75-12624, United Nations, Geneva, Switzerland.
2. Glennon, R. A. (2014) Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention Adv. Pharmacol. 69, 581-620
3. - (2013) The challenge of new psychoactive substances, United Nations Office of Drugs and Crime, Vienna, Austria.
4. Baumann, M. H., Partilla, J. S., and Lehner, K. R. (2013) Psychoactive 'bath salts': not so soothing Eur. J. Pharmacol. 698, 1-5
5. - (2012) Synthetic Drug Abuse Prevention Act, Section 1152. Addition of synthetic drugs to Schedule I of the Controlled Substances Act, pp 138-140, http://www.gpo.gov/fdsys/pkg/BILLS-112s3187enr/pdf/BILLS-112s3187enr.pdf.
6. 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 38, 552-562
7. Cameron, K., Kolanos, R., Verkariya, R., De Felice, L., and Glennon, R. A. (2013) Mephedrone and methylenedioxypyrovalerone (MDPV), major constituents of 'bath salts,' produce opposite effects at the human dopamine transporter Psychopharmacology 227, 493-499
8. Simmler, L. D., Buser, T. A., Donzelli, M., Schramm, Y., Dieu, 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
9. 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, 803-815
10. Cameron, K. N., Kolanos, R., Solis, E., Glennon, R. A., and De Felice, L. J. (2013) Bath salts components mephedrone and methylenedioxypyrovalerone (MDPV) act synergistically at the human dopamine transporter Br. J. Pharmacol. 68, 1750-1757
11. Kolanos, R., Solis, E., Sakloth, F., De Felice, L. J., and Glennon, R. A. (2013) 'Deconstruction' of the abused synthetic cathinone methylenedioxypyrovalerone (MDPV) and an examination of effects at the human dopamine transporter ACS Chem. Neurosci. 4, 1524-1529
12. Negus, S. S. and Miller, L. L. (2014) Intracranial self-stimulation (ICSS) to evaluate abuse potential of drugs Pharmacol. Rev. 66, 869-917
13. 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
14. Bonano, J. S., Runyon, S. P., Hassler, C., Glennon, R. A., and Negus, S. S. (2014) Effects of the neuropeptide S receptor antagonist RTI-118 on abuse-related facilitation of intracranial self-stimulation produced by cocaine and methylenedioxypyrovalerone (MDPV) in rats Eur. J. Pharmacol. 743, 98-105
15. Bonano, J. S., Glennon, R. A., De Felice, L. J., Banks, M. L., and Negus, S. S. (2014) Abuse-related and abuse-limiting effects of methcathinone and the synthetic 'bath salts' cathinone analogs methylenedioxypyrovalerone (MDPV), methylone and mephedrone on intracranial self-stimulation in rats Psychopharmacology 231, 199-207
16. Rosenberg, M. B., Carroll, F. I., and Negus, S. S. (2013) Effects of monoamine reuptake inhibitors in assays of acute pain-stimulated and pain-depressed behavior in rats J. Pain 14, 246-259
17. Nájera, C., Abellán, T., and Sansano, J. M. (2000) Asymmetric synthesis of α-methyl α-amino acids through diastereoselective alkylation under mild reaction conditions of an alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure Eur. J. Org. Chem. 15, 2809-2820
18. Sasaki, N. A., Hashimoto, Ch., and Potier, P. (1987) A novel approach to the synthesis of optically pure non protein α-amino acids in both l and d configurations from l -serine Tetrahedron Lett. 28, 6069-6072