Prolintane

Prolintane
Clinical data
Trade names	Catovit, Katovit, Promotil, Villescon
Routes of; administration	By mouth, intranasal, rectal
Drug class	Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI)
ATC code	N06BX14 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs);
Identifiers
	IUPAC name 1-(1-phenylpentan-2-yl)pyrrolidine;
CAS Number	493-92-5 ;
PubChem CID	14592;
ChemSpider	13930 ;
UNII	EM4YZW677H;
ChEMBL	ChEMBL2111047 ;
CompTox Dashboard (EPA)	DTXSID70862031 ;
ECHA InfoCard	100.007.077
Chemical and physical data
Formula	C15H23N
Molar mass	217.356 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	133 °C (271 °F)
Boiling point	153 °C (307 °F)
	SMILES CCCC(N1CCCC1)CC2=CC=CC=C2;
	InChI InChI=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 ; Key:OJCPSBCUMRIPFL-UHFFFAOYSA-N ;
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Prolintane is a central nervous system (CNS) stimulant^[2] and norepinephrine–dopamine reuptake inhibitor (NDRI) of the phenylalkylpyrrolidine family developed in the 1950s.^[3] 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.^[4] Many cases of prolintane abuse have been reported.^[5]

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.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Hollister LE, Gillespie HK (March–April 1970). "A new stimulant, prolintane hydrochloride, compared with dextroamphetamine in fatigued volunteers". The Journal of Clinical Pharmacology and the Journal of New Drugs. 10 (2): 103–9. doi:10.1177/009127007001000205. PMID 4392006.
^ GB Patent 807835
^ Nicholson AN, Stone BM, Jones MM (November 1980). "Wakefullness and reduced rapid eye movement sleep: studies with prolintane and pemoline". British Journal of Clinical Pharmacology. 10 (5): 465–72. doi:10.1111/j.1365-2125.1980.tb01790.x. PMC 1430138. PMID 7437258.
^ Kyle PB, Daley WP (September 2007). "Domestic abuse of the European rave drug prolintane". Journal of Analytical Toxicology. 31 (7): 415–8. doi:10.1093/jat/31.7.415. PMID 17725890.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] Hollister LE, Gillespie HK (March–April 1970). "A new stimulant, prolintane hydrochloride, compared with dextroamphetamine in fatigued volunteers". The Journal of Clinical Pharmacology and the Journal of New Drugs. 10 (2): 103–9. doi:10.1177/009127007001000205. PMID 4392006.

[3] GB Patent 807835

[4] Nicholson AN, Stone BM, Jones MM (November 1980). "Wakefullness and reduced rapid eye movement sleep: studies with prolintane and pemoline". British Journal of Clinical Pharmacology. 10 (5): 465–72. doi:10.1111/j.1365-2125.1980.tb01790.x. PMC 1430138. PMID 7437258.

[5] Kyle PB, Daley WP (September 2007). "Domestic abuse of the European rave drug prolintane". Journal of Analytical Toxicology. 31 (7): 415–8. doi:10.1093/jat/31.7.415. PMID 17725890.

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