Pyrovalerone

Pyrovalerone

Systematic (IUPAC) name
(RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
Clinical data
Legal status	AU: S4 (Prescription only) DE: Anlage II (Prohibited) US: Schedule V
Routes of administration	Oral
Identifiers
CAS Number	3563-49-3 N 1147-62-2 (hydrochloride)
ATC code	none
PubChem	CID: 14373
ChemSpider	13733 Y
UNII	VOU69C02JP Y
ChEMBL	CHEMBL201960 Y
Chemical data
Formula	C16H23NO
Molecular mass	245.36 g/mol
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 Y Key:SWUVZKWCOBGPTH-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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), and is used for the clinical treatment of chronic fatigue or lethargy 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. Pyrovalerone is a Schedule V controlled substance in the United States (U.S.). In Britain, it is in the Class C category and In Australia it is a Schedule 4 substance. 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.

See also

• α-Pyrrolidinohexiophenone (α-PHP)
• α-Pyrrolidinopentiothiophenone (α-PVT)
• Methylenedioxypyrovalerone (MDPV)
• Naphyrone (O-2482)
• Prolintane (Promotil, Katovit)
• 4'-Methyl-α-pyrrolidinohexiophenone The hexyl analogue.