Pyrovalerone

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464377734

| IUPAC_name = (RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)pentan-1-one

| image = Pyrovalerone.svg

| image_class = skin-invert-image

| width = 200px

| image2 = Pyrovalerone3d.png

| image_class2 = bg-transparent

| chirality = Racemic mixture

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU = S4

| legal_BR = B1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule IV

| legal_US = Schedule V

| legal_UK = Class C

| legal_DE = Anlage II

| routes_of_administration = By mouth

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 3563-49-3

| CAS_supplemental =
1147-62-2 (hydrochloride)

| ATC_prefix = none

| PubChem = 14373

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13733

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = VOU69C02JP

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 201960

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05663

| C = 16

| H = 23

| N = 1

| O = 1

| smiles = O=C(C(CCC)N1CCCC1)C2=CC=C(C)C=C2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SWUVZKWCOBGPTH-UHFFFAOYSA-N

}}

Pyrovalerone (Centroton, 4-Methyl-β-keto-prolintane, Thymergix, O-2371)US Patent 3314970 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{{cite journal | vauthors = Gardos G, Cole JO | title = Evaluation of pyrovalerone in chronically fatigued volunteers | journal = Current Therapeutic Research, Clinical and Experimental | volume = 13 | issue = 10 | pages = 631–5 | date = October 1971 | pmid = 4402508 }} and as an appetite suppressant, but was withdrawn from both markets around 2001 due to safety concerns including problems with abuse and dependence.{{cite journal | vauthors = Deniker P, Lôo H, Cuche H, Roux JM | title = [Abuse of pyrovalerone by drug addicts] | journal = Annales médico-psychologiques | volume = 2 | issue = 4 | pages = 745–8 | date = November 1975 | pmid = 9895 }} 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.

The R-enantiomer of pyrovalerone is devoid of pharmacologic activity.{{cite journal | vauthors = Meltzer PC, Butler D, Deschamps JR, Madras BK | title = 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 4 | pages = 1420–32 | date = February 2006 | pmid = 16480278 | pmc = 2602954 | doi = 10.1021/jm050797a }}