WIN-35428
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| Other names | CFT, WIN 35,428 |
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| Specific rotation | -62.5° |
| Melting point | 202 to 204 °C (396 to 399 °F) |
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(–)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane (β-CFT, WIN 35,428) is a stimulant drug used in scientific research. CFT is a phenyltropane based dopamine reuptake inhibitor and is structurally derived from cocaine. It is around 3-10x more potent than cocaine and lasts around 7 times longer based on animal studies. While the naphthalenedisulfonate salt is the most commonly used form in scientific research due to its high solubility in water, the free base and hydrochloride salts are known compounds and can also be produced. The tartrate is another salt form that is reported.[1]
Uses
CFT was first reported by Clarke and co-workers in 1973.
CFT is about as addictive as cocaine in animal studies, but is taken less often due to its longer duration of action. Potentially this could make it a suitable drug to be used as a substitute for cocaine, in a similar manner to how methadone is used as a substitute for opiates in treating addiction.
Street drug
In August 2010, some media sources claimed that the
Legal status
CFT is not specifically scheduled in the United States,[5] though it meets the statutory definition of an ecgonine derivative. Consequently, it is a Schedule II drug.[6]
Toxicity
Administering 100 mg/kg of CFT to rats only resulted in convulsions being reported, whereas CIT had the ability to cause death at this dose.[7]
See also
- WIN 35,065-2
- List of phenyltropanes
- List of cocaine analogues
References
- ^ PMID 15957006.
- S2CID 8105834.
- ^ "Ivory Wave: The new meow meow?". Metro.co.uk. 2010-08-17. Retrieved 2010-08-23.
- ^ Jones S, Power M (2010-08-17). "Ivory Wave drug implicated in death of 24-year-old man | Society | guardian.co.uk". London: Guardian. Retrieved 2010-08-23.
- ^ "DEA, Drug Scheduling". Archived from the original on 2013-06-29. Retrieved 2011-04-07.
- ^ "21 USC 812: Schedules of controlled substances". uscode.house.gov. Retrieved 2023-07-18.
Further reading
- D'Mello GD, Goldberg DM, Goldberg SR, Stolerman IP (December 1979). "Conditioned taste aversion and operant behaviour in rats: effects of cocaine and a cocaine analogue (WIN 35,428)". Neuropharmacology. 18 (12): 1009–1010. S2CID 31564203.
- Reith ME, Sershen H, Lajtha A (September 1980). "Saturable (3H)cocaine binding in central nervous system of mouse". Life Sciences. 27 (12): 1055–1062. PMID 6106874.
- Spealman RD, Bergman J, Madras BK (August 1991). "Self-administration of the high-affinity cocaine analog 2 beta-carbomethoxy-3 beta-(4-fluorophenyl)tropane". Pharmacology, Biochemistry, and Behavior. 39 (4): 1011–1013. S2CID 53272758.
- Milius RA, Saha JK, Madras BK, Neumeyer JL (May 1991). "Synthesis and receptor binding of N-substituted tropane derivatives. High-affinity ligands for the cocaine receptor". Journal of Medicinal Chemistry. 34 (5): 1728–1731. S2CID 22777518.
- Cline EJ, Scheffel U, Boja JW, Carroll FI, Katz JL, Kuhar MJ (March 1992). "Behavioral effects of novel cocaine analogs: a comparison with in vivo receptor binding potency". The Journal of Pharmacology and Experimental Therapeutics. 260 (3): 1174–1179. PMID 1545384.
- Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists". Chemical Reviews. 100 (3): 925–1024. S2CID 36764655.
- Li SM, Campbell BL, Katz JL (June 2006). "Interactions of cocaine with dopamine uptake inhibitors or dopamine releasers in rats discriminating cocaine". The Journal of Pharmacology and Experimental Therapeutics. 317 (3): 1088–1096. S2CID 28919339.
- Kline RH, Wright J, Fox KM, Eldefrawi ME (July 1990). "Synthesis of 3-arylecgonine analogues as inhibitors of cocaine binding and dopamine uptake". Journal of Medicinal Chemistry. 33 (7): 2024–2027. PMID 2362282.
- Xu L, Trudell ML (November 1996). "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. 33 (6): 2037–9. .