α-Pyrrolidinopentiophenone

α-Pyrrolidinopentiophenone
Clinical data
Other names	α-Pyrrolidinovalerophenone; α-PVP; O-2387; β-Keto-prolintane; Prolintanone; Desmethylpyrovalerone
Addiction; liability	Very high
Routes of; administration	By mouth, intranasal, inhalation, sublingual, intravenous
Drug class	Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI)
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class F2 (Prohibited psychotropics); CA: Unscheduled; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Unscheduled; UK: Class B; US: Schedule I; UN: Psychotropic Schedule II;
Pharmacokinetic data
Elimination half-life	2 hours
Duration of action	3–5 hours
Identifiers
	IUPAC name (RS)-1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-one;
CAS Number	14530-33-7 ;
PubChem CID	11148955;
ChemSpider	9324063 ;
UNII	767K3AWA4R;
KEGG	C22754 ;
ChEBI	CHEBI:234463;
ChEMBL	ChEMBL205082 ;
CompTox Dashboard (EPA)	DTXSID70456954 ;
Chemical and physical data
Formula	C15H21NO
Molar mass	231.339 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(C(C1=CC=CC=C1)=O)N2CCCC2;
	InChI InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3 ; Key:YDIIDRWHPFMLGR-UHFFFAOYSA-N ;
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α-Pyrrolidinovalerophenone (α-PVP), also known as α-pyrrolidinopentiophenone , O-2387, β-keto-prolintane, prolintanone,^[2]^[3] or desmethylpyrovalerone, colloquially, it is sometimes called flakka or gravel,^[4]^[5] is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons.^[6]^[7]^[8] α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.^[9]

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ "PubChem Substance Record for SID 481087126, alpha-PVP". National Center for Biotechnology Information. May 9, 2023. Retrieved May 7, 2024.
^ "PubChem Substance Record for SID 172113243, alpha-Pyrrolidinovalerophenone". National Center for Biotechnology Information. March 3, 2023. Retrieved May 7, 2024.
^ Coubrough J (November 2, 2017). "'Zombie drug' flakka may have hit Winnipeg streets: police". CBC News.
^ England C, Garcia F (August 17, 2016). "Flakka: What is the 'zombie drug' blamed for face-eating attacks?". The Independent. Archived from the original on 2016-08-18.
^ Kolesnikova TO, Khatsko SL, Demin KA, Shevyrin VA, Kalueff AV (January 2019). "DARK Classics in Chemical Neuroscience: α-Pyrrolidinovalerophenone ("Flakka")". ACS Chem Neurosci. 10 (1): 168–174. doi:10.1021/acschemneuro.8b00525. PMID 30384587.
^ GB 927475, "α-Pyrrolidinovalerophenones", published May 29, 1963
^ Logan BK (September 13, 2013). "SOFT Designer Drug Committee Monographs: Alpha-PVP" (PDF). Society of Forensic Toxicologists. Archived from the original (PDF) on April 6, 2015.
^ Sauer C, Peters FT, Haas C, Meyer MR, Fritschi G, Maurer HH (June 2009). "New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques". Journal of Mass Spectrometry. 44 (6): 952–64. Bibcode:2009JMSp...44..952S. doi:10.1002/jms.1571. PMID 19241365.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] "PubChem Substance Record for SID 481087126, alpha-PVP". National Center for Biotechnology Information. May 9, 2023. Retrieved May 7, 2024.

[3] "PubChem Substance Record for SID 172113243, alpha-Pyrrolidinovalerophenone". National Center for Biotechnology Information. March 3, 2023. Retrieved May 7, 2024.

[4] Coubrough J (November 2, 2017). "'Zombie drug' flakka may have hit Winnipeg streets: police". CBC News.

[5] England C, Garcia F (August 17, 2016). "Flakka: What is the 'zombie drug' blamed for face-eating attacks?". The Independent. Archived from the original on 2016-08-18.

[KolesnikovaKhatskoDemin2019-6] Kolesnikova TO, Khatsko SL, Demin KA, Shevyrin VA, Kalueff AV (January 2019). "DARK Classics in Chemical Neuroscience: α-Pyrrolidinovalerophenone ("Flakka")". ACS Chem Neurosci. 10 (1): 168–174. doi:10.1021/acschemneuro.8b00525. PMID 30384587.

[7] GB 927475, "α-Pyrrolidinovalerophenones", published May 29, 1963

[8] Logan BK (September 13, 2013). "SOFT Designer Drug Committee Monographs: Alpha-PVP" (PDF). Society of Forensic Toxicologists. Archived from the original (PDF) on April 6, 2015.

[9] Sauer C, Peters FT, Haas C, Meyer MR, Fritschi G, Maurer HH (June 2009). "New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques". Journal of Mass Spectrometry. 44 (6): 952–64. Bibcode:2009JMSp...44..952S. doi:10.1002/jms.1571. PMID 19241365.

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