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Troparil

 
 
 


Identification
Name Troparil
Synonymous (-)-2β-Carbomethoxy-3β-phenyltropane; 2-beta-Methoxycarbonyl-3-beta-phenyltropane; (exo,exo)-8-Methyl-3-phenyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid methyl ester; WIN 35065; β-CPT
CAS Number 74163-84-1
Molecular Structure


Molecular Formula C16H21NO2
Molecular Weight 259.35

Properties
Melting Point 190-191 °C

Notes

(-)-2β-Carbomethoxy-3β-phenyltropane (Troparil, β-CPT, WIN-35065-2) is a stimulant drug used in scientific research. CPT is a phenyltropane based dopamine reuptake inhibitor and is derived from methylecgonidine. It is around the same potency as cocaine but lasts several times longer due to the lack of the metabolically labile ester link between the phenyl and tropane rings. The lack of an ester linkage removes the local anesthetic action from the drug, so CPT is a pure stimulant. This change in activity also makes CPT slightly less cardiotoxic than cocaine. The most commonly used form of β-CPT is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base.

Uses

CPT is used in scientific research into the dopamine reuptake transporter. 3H-radiolabelled forms of CPT have been used in humans and animals to map the distribution of dopamine transporters in the brain. [1][2] It is also used for animal research into stimulant drugs as an alternative to cocaine which produces similar effects,[3] but avoids the stringent licensing requirements for the use of cocaine itself.

β-CPT has similar effects to cocaine in animal studies,[4][5] but no instances of this compound being abused recreationally by humans are known. Despite being easily made by the reaction of methylecgonidine with phenylmagnesium bromide,[6][7] the relative scarcity of methylecgonidine and the demanding reaction conditions required for the synthesis[8][9] put production of this compound beyond the capacity of most illicit drug manufacturers, and legitimate supplies of β-CPT are available only in very small quantities for a very high price.

 

Legal Status

The legal status of CPT is unclear. Sigma-Aldrich claims that it is a Schedule II / Class B drug in the USA and UK,[10] but it is not listed in any controlled drugs legislation or published lists of illegal drugs from the relevant government departments in these jurisdictions. Nevertheless, CPT may be considered a controlled substance analogue of cocaine on the grounds of its related chemical structure in some jurisdictions such as Canada, Australia and New Zealand.

This is somewhat unclear as there has not been any legal precedent set to determine whether a compound derived by the simplification of an illegal drug molecule (removal of an ester link in this instance) can be considered "substantially similar" to the illegal drug; all previous examples of designer drugs such as α-methylfentanyl have been derived instead by adding extra substituent groups onto the molecule, and the laws covering this area only refer to the addition or substitution of groups onto the illegal drug molecule, not their removal. An excessively broad precedent set in this area would be extremely problematic from a legal standpoint.

References

  1. ^ Ritz M.C. et al. [3H]WIN 35,065-2: a ligand for cocaine receptors in striatum. J. Neurochem. 1990, 55, 1556-1562.
  2. ^ Scheffel U. et al. Cocaine receptors: In Vivo Labelling with 3H-(-) cocaine, 3H-WIN 35,065-2, and 3H-WIN 35,428. Synapse 1989, 4, 390-392.
  3. ^ Zakusov VV, Naumova BI. Pharmacology of troparil. Farmakologiia i Toksikologiia. 1985 Jan-Feb;48(1):15-9.
  4. ^ Balster RL, Carroll FI, Graham JH, Mansbach RS, Rahman MA, Philip A, Lewin AH, Showalter VM. Potent substituted-3 beta-phenyltropane analogs of cocaine have cocaine-like discriminative stimulus effects. Drug and Alcohol Dependence. 1991 Dec 31;29(2):145-51. PMID 1797525
  5. ^ Xu L, Kelkar SV, Lomenzo SA, Izenwasser S, Katz JL, Kline RH, Trudell ML. Synthesis, dopamine transporter affinity, dopamine uptake inhibition, and locomotor stimulant activity of 2-substituted 3 beta-phenyltropane derivatives. Journal of Medicinal Chemistry. 1997 Mar 14;40(6):858-63. PMID 9083474
  6. ^ Clarke RL, Daum SJ, Gambino AJ, Aceto MD, Pearl J, Levitt M, Cumiskey WR, Bogado EF. Compounds affecting the central nervous system. 4. 3 Beta-phenyltropane-2-carboxylic esters and analogs. Journal of Medicinal Chemistry. 1973 Nov;16(11):1260-7. PMID 4747968
  7. ^ Kline RH Jr, Wright J, Fox KM, Eldefrawi ME. Synthesis of 3-arylecgonine analogues as inhibitors of cocaine binding and dopamine uptake. Journal of Medicinal Chemistry. 1990 Jul;33(7):2024-7. PMID 2362282
  8. ^ Xu L, Trudell ML. Stereoselective Synthesis of 2β-Carbomethoxy-3β-Phenyltropane Derivatives. Enhanced Stereoselectivity Observed for the Conjugate Addition Reaction of Phenylmagnesium Bromide Derivatives with Anhydro Dichloromethane. Journal of Heterocyclic Chemistry. 1996; 33(6): 2037-2039.
  9. ^ Milius RA, Saha JK, Madras BK, Neumeyer JL. Synthesis and receptor binding of N-substituted tropane derivatives. High-affinity ligands for the cocaine receptor. Journal of Medicinal Chemistry. 1991 May;34(5):1728-31. PMID 2033595
  10. ^ Sigma-Aldrich pharmacutical page for Troparil/CPT

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