Troparil

Troparil

Clinical data
ATC code	none
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 Y
PubChem CID	170832
ChemSpider	149355
ChEMBL	CHEMBL298684 N
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.343 g/mol
3D model (Jmol)	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
NY (what is this?)

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, but is less potent as a serotonin reuptake inhibitor, 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. 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.

The first known published synthesis of troparil and the related compound WIN 35428 is by Clarke and co-workers during the 1970s. Apparently, it was their intention to separate the stimulant actions of cocaine from its toxicity and dependence liability. Troparil is the only regular phenyltropane having a NET affinity that exceeds the DAT affinity.

Phenyltropanes are likely to have less abuse and dependency compared with cocaine.

Troparil is used in scientific research into the dopamine reuptake transporter. ³H-radiolabelled forms of troparil have been used in humans and animals to map the distribution of dopamine transporters in the brain. It is also used for animal research into stimulant drugs as an alternative to cocaine which produces similar effects, but avoids the stringent licensing requirements for the use of cocaine itself.