Pyrovalerone

Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371)^[2] is a central nervous system (CNS) stimulant that acts 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briefly been approved in Spain and France for chronic fatigue or lethargy^[3] and as an appetite suppressant, but was withdrawn from both markets around 2001 due to safety concerns including problems with abuse and dependence.^[4] It is closely related on a structural level to a number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.

Routes of
administrationBy mouth

ATC code

• none

Legal status

• AU: S4 (Prescription only)
• BR: Class B1 (Psychoactive drugs)^[1]
• CA: Schedule IV
• DE: Anlage II (Authorized trade only, not prescriptible)
• UK: Class C
• US: Schedule V

CAS Number

• 3563-49-3 ^N
  1147-62-2 (hydrochloride)

Quick facts Clinical data, Routes ofadministration ...

Pyrovalerone

Clinical data
Routes of administration	By mouth
ATC code	none
Legal status
Legal status	AU: S4 (Prescription only) BR: Class B1 (Psychoactive drugs)[1] 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 N 1147-62-2 (hydrochloride)
PubChem CID	14373
ChemSpider	13733 Y
UNII	VOU69C02JP
KEGG	D05663 Y
ChEMBL	ChEMBL201960 Y
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 Y Key:SWUVZKWCOBGPTH-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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Side effects of pyrovalerone include decreased appetite, anxiety, fragmented sleep or insomnia, and trembling, shaking, or muscle tremors. Withdrawal symptoms following abuse upon discontinuation often results in depression.

The R-enantiomer of pyrovalerone is devoid of pharmacologic activity.^[5]