prolintane

{{Short description|Stimulant and NDRI drug}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| class = Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI)

| verifiedrevid = 464215530

| IUPAC_name = 1-(1-phenylpentan-2-yl)pyrrolidine

| image = Prolintane.svg

| image_class = skin-invert-image

| image2 = Prolintane3d.png

| image_class2 = bg-transparent

| tradename = Catovit, Katovit, Promotil, Villescon

| 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 =

| legal_UK =

| legal_US =

| routes_of_administration = By mouth, intranasal, rectal

| CAS_number_Ref = {{cascite|changed|cas}}

| CAS_number = 493-92-5

| ATC_prefix = N06

| ATC_suffix = BX14

| PubChem = 14592

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

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

| ChemSpiderID = 13930

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

| UNII = EM4YZW677H

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2111047

| C = 15

| H = 23

| N = 1

| smiles = CCCC(N1CCCC1)CC2=CC=CC=C2

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

| StdInChI = 1S/C15H23N/c1-2-8-15(16-11-6-7-12-16)13-14-9-4-3-5-10-14/h3-5,9-10,15H,2,6-8,11-13H2,1H3

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

| StdInChIKey = OJCPSBCUMRIPFL-UHFFFAOYSA-N

| melting_point = 133

| boiling_point = 153

}}

Prolintane is a central nervous system (CNS) stimulant{{cite journal | vauthors = Hollister LE, Gillespie HK | title = A new stimulant, prolintane hydrochloride, compared with dextroamphetamine in fatigued volunteers | journal = The Journal of Clinical Pharmacology and the Journal of New Drugs | volume = 10 | issue = 2 | pages = 103–9 | date = March–April 1970 | pmid = 4392006 | doi = 10.1177/009127007001000205 }} and norepinephrine–dopamine reuptake inhibitor (NDRI) of the phenylalkylpyrrolidine family developed in the 1950s.GB Patent 807835 Being an amphetamine derivative, it is closely related in chemical structure to other drugs such as pyrovalerone, MDPV, and propylhexedrine, and has a similar mechanism of action.{{cite journal | vauthors = Nicholson AN, Stone BM, Jones MM | title = Wakefullness and reduced rapid eye movement sleep: studies with prolintane and pemoline | journal = British Journal of Clinical Pharmacology | volume = 10 | issue = 5 | pages = 465–72 | date = November 1980 | pmid = 7437258 | pmc = 1430138 | doi = 10.1111/j.1365-2125.1980.tb01790.x }} Many cases of prolintane abuse have been reported.{{cite journal | vauthors = Kyle PB, Daley WP | title = Domestic abuse of the European rave drug prolintane | journal = Journal of Analytical Toxicology | volume = 31 | issue = 7 | pages = 415–8 | date = September 2007 | pmid = 17725890 | doi = 10.1093/jat/31.7.415 | doi-access = free }}

Under the brand name Katovit, prolintane was commercialized by the Spanish pharmaceutical company FHER until 2001. It was most often used by students and workers as a stimulant to provide energy and increase alertness and concentration.{{medcn|date=November 2023}}