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Pyrovalerone

Summary

Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371)[2] is a psychoactive drug with stimulant effects via acting as a norepinephrine-dopamine reuptake inhibitor (NDRI). It was developed in the 1980s and had briefly been approved in Spain and France for chronic fatigue or lethargy[3] and as an anorectic or appetite suppressant, but was withdrawn from both markets around 2001 due to safety concerns including problems with abuse and dependence.[4] It is closely related on a structural level to a number of other cathinone stimulants, such as α-PVP, MDPV and prolintane (Promotil, Katovit).

Pyrovalerone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • (RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
CAS Number
  • 3563-49-3 ☒N
    1147-62-2 (hydrochloride)
PubChem CID
  • 14373
ChemSpider
  • 13733 checkY
UNII
  • VOU69C02JP
KEGG
  • D05663 checkY
ChEMBL
  • ChEMBL201960 checkY
CompTox Dashboard (EPA)
  • DTXSID20863194 Edit this at Wikidata
ECHA InfoCard100.230.426 Edit this at Wikidata
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
  • O=C(C(CCC)N1CCCC1)C2=CC=C(C)C=C2
  • InChI=1S/C16H23NO/c1-3-6-15(17-11-4-5-12-17)16(18)14-9-7-13(2)8-10-14/h7-10,15H,3-6,11-12H2,1-2H3 checkY
  • Key:SWUVZKWCOBGPTH-UHFFFAOYSA-N checkY
 ☒NcheckY (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 pharmacologic activity.[5]

See also edit

 
Look up pyrovalerone in Wiktionary, the free dictionary.

References edit

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ US Patent 3314970
  3. ^ Gardos G, Cole JO (October 1971). "Evaluation of pyrovalerone in chronically fatigued volunteers". Current Therapeutic Research, Clinical and Experimental. 13 (10): 631–5. PMID 4402508.
  4. ^ Deniker P, Lôo H, Cuche H, Roux JM (November 1975). "[Abuse of pyrovalerone by drug addicts]". Annales médico-psychologiques. 2 (4): 745–8. PMID 9895.
  5. ^ Meltzer PC, Butler D, Deschamps JR, Madras BK (February 2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry. 49 (4): 1420–32. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.