Pyrovalerone

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Pyrovalerone
Pyrovalerone.svg
Systematic (IUPAC) name
(RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
Clinical data
Legal statusPrescription Only (S4) (AU) Schedule V (US)
RoutesOral
Identifiers
CAS number3563-49-3 N
1147-62-2 (hydrochloride)
ATC codeNone
PubChemCID 14373
ChemSpider13733 YesY
UNIIVOU69C02JP YesY
ChEMBLCHEMBL201960 YesY
Chemical data
FormulaC16H23NO 
Mol. mass245.36 g/mol
 N (what is this?)  (verify)
 
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Pyrovalerone
Pyrovalerone.svg
Systematic (IUPAC) name
(RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
Clinical data
Legal statusPrescription Only (S4) (AU) Schedule V (US)
RoutesOral
Identifiers
CAS number3563-49-3 N
1147-62-2 (hydrochloride)
ATC codeNone
PubChemCID 14373
ChemSpider13733 YesY
UNIIVOU69C02JP YesY
ChEMBLCHEMBL201960 YesY
Chemical data
FormulaC16H23NO 
Mol. mass245.36 g/mol
 N (what is this?)  (verify)

Pyrovalerone (Centroton, 4-Methyl-β-ketone-prolintane, Thymergix, O-2371)[1] is a psychoactive drug with stimulant effects via acting as a norepinephrine-dopamine reuptake inhibitor (NDRI), and is used for the clinical treatment of chronic fatigue or lethargy[2] and as an anorectic or appetite suppressant for weight loss purposes. It was developed in the late 1960s and has since been used in France and several other European countries. Though pyrovalerone is still occasionally prescribed, it is used infrequently due to problems with abuse and dependence.[3] Pyrovalerone is a Schedule V controlled substance in the United States (U.S.).[4] In Britain, it is in the Class C category and In Australia it is a Schedule 4 substance.[5] It is closely related on a structural level to a number of other stimulants, such as MDPV and prolintane (Promotil, Katovit).

Side effects of pyrovalerone include anorexia or loss of appetite, anxiety, fragmented sleep or insomnia, and trembling, shaking, or muscle tremors. Withdrawal following abuse upon discontinuation often results in depression.

The R-enantiomer of pyrovalerone is devoid of activity.[6]

See also[edit]

References[edit]

  1. ^ US Patent 3314970
  2. ^ Gardos, G.; Cole, J. O. (1971). "Evaluation of pyrovalerone in chronically fatigued volunteers". Current therapeutic research, clinical and experimental 13 (10): 631–635. PMID 4402508.  edit
  3. ^ Deniker, P.; Lôo, H.; Cuche, H.; Roux, J. M. (1975). "Abuse of pyrovalerone by drug addicts". Annales medico-psychologiques 2 (4): 745–748. PMID 9895.  edit
  4. ^ "Schedule V Controlled Substances". Retrieved 2008-01-13. 
  5. ^ "Uniform Scheduling of Drugs and Poisons No. 24 AUS (2009)". Retrieved 2010-04-14. 
  6. ^ Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. (2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogs. A promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry 49 (4): 1420–1432. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.  edit