Pyrovalerone

Pyrovalerone (Centroton, 4-Methyl-β-keto-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, and although pyrovalerone is still occasionally prescribed, it is used infrequently due to problems with abuse and dependence.[3] It is closely related on a structural level to a number of other stimulants, such as MDPV and prolintane (Promotil, Katovit).

Pyrovalerone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: Schedule IV
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class C
  • US: Schedule V
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.230.426
Chemical and physical data
FormulaC16H23NO
Molar mass245.36 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
 NY (what is this?)  (verify)

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.[4]

See also

References
  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.
  3. Deniker, P.; Lôo, H.; Cuche, H.; Roux, J. M. (1975). "Abuse of pyrovalerone by drug addicts". Annales Médico-Psychologiques. 2 (4): 745–748. PMID 9895.
  4. 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.


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