Structure via PubChem · Public domain (PubChem)
pyrovalerone
Sign in to saveAlso known as O-2371, 4-methyl-β-keto-prolintane
Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371) 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had briefly been approved in Spain and France for chronic fatigue or lethargy and as an appetite suppressant, but was withdrawn from both markets around 2001 due to safety concerns including problems with abuse and dependence.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.
Chemical data
- Formula
- C16H23NO
- Molecular weight
- 245.36 g/mol
- IUPAC name
- 1-(4-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one
- SMILES
- CCCC(C(=O)C1=CC=C(C=C1)C)N2CCCC2
- InChIKey
- SWUVZKWCOBGPTH-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 20.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
90 papers- [3,4-methylene-dioxy-pyrovalerone (MDPV) epidemic?].Orvosi hetilap · 2011
- The psychoactive cathinone derivative pyrovalerone alters locomotor activity and decreases dopamine receptor expression in zebrafish (Danio rerio).Brain and behavior · 2019
- Persistent binding at dopamine transporters determines sustained psychostimulant effects.Proceedings of the National Academy of Sciences of the United States of America · 2023
- Danio rerio embryo as in vivo model for the evaluation of the toxicity and metabolism of pyrovalerone cathinones.Ecotoxicology and environmental safety · 2024
- The Pharmacological Profile of Second Generation Pyrovalerone Cathinones and Related Cathinone Derivative.International journal of molecular sciences · 2021
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 245.178
Show 5 more facts
- Commons category
- Pyrovalerone
- chemical formula
- C₁₆H₂₃NO
- canonical SMILES
- CCCC(C(=O)C1=CC=C(C=C1)C)N2CCCC2
- subject has role
- stimulant
- MCN code
- 2933.91.72
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371) 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 and as an 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.
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.
Excerpted from Wikipedia’s “pyrovalerone” article, available under the CC BY-SA 4.0 licence.