Pyrovalerone

Pyrovalerone

Systematic (IUPAC) name
(RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one
Clinical data
Routes of administration	Oral
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage II (Prohibited) UK: Class C US: Schedule V
Identifiers
CAS Number	3563-49-3 1147-62-2 (hydrochloride)
ATC code	none
PubChem	CID 14373
ChemSpider	13733
UNII	VOU69C02JP
ChEMBL	CHEMBL201960
Chemical data
Formula	C16H23NO
Molar mass	245.36 g/mol
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)^[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

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

References

1. US Patent 3314970
2. Gardos, G.; Cole, J. O. (1971). "Evaluation of pyrovalerone in chronically fatigued volunteers". Current therapeutic research, clinical and experimental 13 (10): 631–635. PMID 4402508.
3. Deniker, P.; Lôo, H.; Cuche, H.; Roux, J. M. (1975). "Abuse of pyrovalerone by drug addicts". Annales médico-psychologiques 2 (4): 745–748. PMID 9895.
4. Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. (2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogs. A promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry 49 (4): 1420–1432. doi:10.1021/jm050797a. PMC: 2602954. PMID 16480278.