WIN-35428

Uses

CFT was first reported by Clarke and co-workers in 1973. This drug is known to function as a "positive reinforcer" (although it is less likely to be self-administered by rhesus monkeys than cocaine). Tritiated CFT is frequently used to map binding of novel ligands to the DAT, although the drug also has some SERT affinity.

Radiolabelled forms of CFT have been used in humans and animals to map the distribution of dopamine transporters in the brain. CFT was found to be particularly useful for this application as a normal fluorine atom can be substituted with the radioactive isotope 18F which is widely used in Positron emission tomography. Another radioisotope-substituted analog [11C]WIN 35,428 (where the carbon atom of either the N-methyl group, or the methyl from the 2-carbomethoxy group of CFT, has been replaced with 11C) is now more commonly used for this application, as it is quicker and easier in practice to make radiolabelled CFT by methylating nor-CFT or 2-desmethyl-CFT than by reacting methylecgonidine with parafluorophenylmagnesium bromide, and also avoids the requirement for a licence to work with the restricted precursor ecgonine.

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 designer drug Ivory Wave contained WIN 35428. However, these reports at the time were poorly researched and sensationalized: the use of the pseudonym 'meow meow' (for Mephedrone) appears to have originated in the UK media. Samples of Ivory Wave were later found to contain MDPV, and the careless and exploitative nature of reporting regarding new psychoactive compounds in this fashion not only served to raise awareness that such compounds were for sale and available to the public-at-large, but posed a significant risk to public health in its own right due to misleading or incorrect information.

Legal status

CFT is not specifically scheduled in the United States, though it meets the statutory definition of an ecgonine derivative. Consequently, it is a Schedule II drug.

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.

References

References

1. (February 2006). "A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants". Neuropsychopharmacology.
2. (November 1973). "Compounds affecting the central nervous system. 4. 3 Beta-phenyltropane-2-carboxylic esters and analogs". Journal of Medicinal Chemistry.
3. (2010-08-17). "Ivory Wave: The new meow meow?". Metro.co.uk.
4. (2010-08-17). "Ivory Wave drug implicated in death of 24-year-old man | Society | guardian.co.uk". Guardian.
5. "DEA, Drug Scheduling".
6. "21 USC 812: Schedules of controlled substances".
7. (December 2004). "Monoamine transporter binding, locomotor activity, and drug discrimination properties of 3-(4-substituted-phenyl)tropane-2-carboxylic acid methyl ester isomers". Journal of Medicinal Chemistry.