Pyrovalerone

Title: Pyrovalerone
CAS Registry Number: 3563-49-3
CAS Name: 1-(4-Methylphenyl)-2-(1-pyrrolidinyl)-1-pentanone
Additional Names: 4¢-methyl-2-(1-pyrrolidinyl)valerophenone; a-pyrrolidino-p-methylvalerophenone; 1-(1-pyrrolidinyl)butyl p-tolyl ketone; 1-(p-tolyl)-1-oxo-2-pyrrolidino-n-pentane; 1-(p-tolyl)-2-pyrrolidino-1-pentanone
Molecular Formula: C16H23NO
Molecular Weight: 245.36
Percent Composition: C 78.32%, H 9.45%, N 5.71%, O 6.52%
Literature References: Prepn: GB 927475 (1963 to Wander); GB 933507; E. Seeger, US 3314970 (1963, 1967 both to Thomae); Heffe, Helv. Chim. Acta 47, 1289 (1964). Pharmacology: Stille et al., Arzneim.-Forsch. 13, 871 (1963). Metabolism: Michaelis et al., J. Med. Chem. 13, 497 (1970).
Properties: bp0.08 104°.
Boiling point: bp0.08 104°
Derivative Type: Hydrochloride
CAS Registry Number: 1147-62-2
Manufacturers' Codes: F-1983
Trademarks: Centroton (Wander); Thymergix (Joulli)
Molecular Formula: C16H23NO.HCl
Molecular Weight: 281.82
Percent Composition: C 68.19%, H 8.58%, N 4.97%, O 5.68%, Cl 12.58%
Properties: Crystals from 2-butanone or from methanol + acetone + diethyl ether, mp 178°. LD50 orally in mice: 350 mg/kg (Stille).
Melting point: mp 178°
Toxicity data: LD50 orally in mice: 350 mg/kg (Stille)
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.15.
Therap-Cat: CNS stimulant.
Keywords: CNS Stimulant.
Pyroxylin Pyrrobutamine Pyrrocaine Pyrrolidine Pyrrolnitrin

Pyrovalerone
Pyrovalerone.svg
Systematic (IUPAC) name
(RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
Clinical data
Legal status Prescription Only (S4) (AU) Schedule V (US)
Routes Oral
Identifiers
CAS number 3563-49-3 N
1147-62-2 (hydrochloride)
ATC code None
PubChem CID 14373
ChemSpider 13733 YesY
UNII VOU69C02JP YesY
ChEMBL CHEMBL201960 YesY
Chemical data
Formula C16H23NO 
Mol. mass 245.36 g/mol
 N (what is this?)  (verify)

Pyrovalerone (Centroton, 4-Methyl-β-ketone-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. Though pyrovalerone is still occasionally prescribed, it is used infrequently due to problems with abuse and dependence.[3] Pyrovalerone is a Schedule V controlled substance in the United States (U.S.).[4] In Britain, it is in the Class C category and In Australia it is a Schedule 4 substance.[5] 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.[6]