Troparil

Troparil
Clinical data
ATC code	none;
Legal status
Legal status	UK: Under Psychoactive Substances Act; US: Schedule II;
Identifiers
	IUPAC name Methyl (1R,2S,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate;
CAS Number	74163-84-1 ;
PubChem CID	170832;
ChemSpider	149355;
UNII	11M96D7J17;
ChEMBL	ChEMBL298684 ;
CompTox Dashboard (EPA)	DTXSID30964641 ;
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.349 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	190 to 191 °C (374 to 376 °F)
	SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=CC=C3)C(=O)OC;
	InChI InChI=1S/C16H21NO2/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14+,15-/m0/s1; Key:OMBOXYLBBHNWHL-YJNKXOJESA-N;
	(what is this?) (verify)

Troparil (also known as (–)-2β-Carbomethoxy-3β-phenyltropane, WIN 35,065-2, or β-CPT) is a stimulant drug used in scientific research. Troparil is a phenyltropane-based dopamine reuptake inhibitor (DRI) that is derived from methylecgonidine. Troparil is a few times more potent than cocaine as a dopamine reuptake inhibitor,^[1] but is less potent as a serotonin reuptake inhibitor,^[2] and has a duration spanning a few times longer, since the phenyl ring is directly connected to the tropane ring through a non-hydrolyzable carbon-carbon bond. The lack of an ester linkage removes the local anesthetic action from the drug, so troparil is a pure stimulant. This change in activity also makes troparil slightly less cardiotoxic than cocaine.^[3] The most commonly used form of troparil is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base.

^ Runyon SP, Carroll FI (2006). "Dopamine transporter ligands: recent developments and therapeutic potential". Current Topics in Medicinal Chemistry. 6 (17): 1825–43. doi:10.2174/156802606778249775. PMID 17017960.
^ Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, et al. (January 1995). "Cocaine and 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter". Journal of Medicinal Chemistry. 38 (2): 379–88. doi:10.1021/jm00002a020. PMID 7830281.
^ Phillips K, Luk A, Soor GS, Abraham JR, Leong S, Butany J (2009). "Cocaine cardiotoxicity: a review of the pathophysiology, pathology, and treatment options". American Journal of Cardiovascular Drugs. 9 (3): 177–96. doi:10.1007/bf03256574. PMID 19463023. S2CID 70385136.

[1] Runyon SP, Carroll FI (2006). "Dopamine transporter ligands: recent developments and therapeutic potential". Current Topics in Medicinal Chemistry. 6 (17): 1825–43. doi:10.2174/156802606778249775. PMID 17017960.

[2] Carroll FI, Kotian P, Dehghani A, Gray JL, Kuzemko MA, Parham KA, et al. (January 1995). "Cocaine and 3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid ester and amide analogues. New high-affinity and selective compounds for the dopamine transporter". Journal of Medicinal Chemistry. 38 (2): 379–88. doi:10.1021/jm00002a020. PMID 7830281.

[3] Phillips K, Luk A, Soor GS, Abraham JR, Leong S, Butany J (2009). "Cocaine cardiotoxicity: a review of the pathophysiology, pathology, and treatment options". American Journal of Cardiovascular Drugs. 9 (3): 177–96. doi:10.1007/bf03256574. PMID 19463023. S2CID 70385136.

[1]

[2]

[3]