Pyrovalerone

Pyrovalerone
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class C; US: Schedule V;
Identifiers
	IUPAC name (RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one;
CAS Number	3563-49-3 ; 1147-62-2 (hydrochloride);
PubChem CID	14373;
ChemSpider	13733 ;
UNII	VOU69C02JP;
KEGG	D05663 ;
ChEMBL	ChEMBL201960 ;
CompTox Dashboard (EPA)	DTXSID20863194 ;
ECHA InfoCard	100.230.426
Chemical and physical data
Formula	C16H23NO
Molar mass	245.366 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic 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 ; Key:SWUVZKWCOBGPTH-UHFFFAOYSA-N ;
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Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371) 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been approved in Spain and France for chronic fatigue or lethargy and as an anorectic or appetite suppressant, but was withdrawn from both markets around 2001 due to safety concerns including problems with abuse and dependence. It is closely related on a structural level to a number of other cathinone stimulants, such as α-PVP, 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 pharmacologic activity.

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