Troparil

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Troparil
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • Methyl (1R,2S,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate
JSmol)
Melting point190 to 191 °C (374 to 376 °F)
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=CC=C3)C(=O)OC
  • 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
 ☒NcheckY (what is this?)  (verify)

Troparil (also known as (–)-2β-Carbomethoxy-3β-phenyltropane, WIN 35,065-2, or β-CPT) is a

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.

Background

The first known published synthesis of troparil and the related compound

]

Application

Phenyltropanes are likely to have less abuse and dependency compared with cocaine.[6][7]

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.[8][9] It is also used for animal research into stimulant drugs as an alternative to cocaine which produces similar effects,[10] but avoids the stringent licensing requirements for the use of cocaine itself.

Troparil has similar effects to cocaine in animal studies,[11][12] but recreational use of this compound to date has proven extremely rare. Despite being easily made by the reaction of methylecgonidine with phenylmagnesium bromide,[5][13] the relative scarcity of methylecgonidine and the demanding reaction conditions required for the synthesis[14][15] put production of this compound beyond the capacity of most illicit drug manufacturers, and legitimate supplies of troparil are available only in very small quantities for a very high price.

Legality

The legal status of troparil is unclear, but it may be considered a

controlled substance analog of cocaine in the United States on the grounds of its related chemical structure. The legal status of troparil and many other cocaine analogs in Canada, is dependent on if ecgonine, coca, or cocaine were derivatives of the compound, according to the wording on the entry of coca in Schedule 1 of the Controlled Drugs and Substances Act.[16]

See also

References