Pyrovalerone

Pyrovalerone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • (RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.230.426
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Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C(C(CCC)N1CCCC1)C2=CC=C(C)C=C2
InChI
  • 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
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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).

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 JO (October 1971). "Evaluation of pyrovalerone in chronically fatigued volunteers". Current Therapeutic Research, Clinical and Experimental. 13 (10): 631–5. PMID 4402508.
  3. ↑ 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.
  4. ↑ 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.


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