4-Methylmethylphenidate

4-Methylmethylphenidate

4-Methylmethylphenidate
Systematic (IUPAC) name
methyl (2R)-2-(4-methylphenyl)-2-[(2R)-piperidin-2-yl]acetate
Clinical data
Legal status
?
Identifiers
ATC code ?
PubChem
ChemSpider  YesY
Chemical data
Formula C15H21NO2 
Mol. mass 247.332 g/mol
 YesY   

threo-4-Methylmethylphenidate (4-MeTMP) is a stimulant drug related to methylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking dopamine reuptake despite its high binding affinity, which led to its investigation as a possible substitute drug for treatment of stimulant abuse (cf. nocaine).[1] On the other hand several other simple ring-substituted derivatives of threo-methylphenidate such as the 4-fluoro and 3-chloro compounds are more potent than methylphenidate both in efficacy as dopamine reuptake inhibitors and in animal drug discrimination assays.[2][3][4]

4-fluoromethylphenidate (4-FTMP) and 3-chloromethylphenidate (3-CTMP)

See also

References

  1. ^ Wayment, H. K.; Deutsch, H.; Schweri, M. M.; Schenk, J. O. (1999). "Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists?". Journal of Neurochemistry 72 (3): 1266–1274.  
  2. ^ Deutsch, H.; Shi, Q.; Gruszecka-Kowalik, E.; Schweri, M. (1996). "Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs".  
  3. ^ Schweri, M. M.; Deutsch, H. M.; Massey, A. T.; Holtzman, S. G. (2002). "Biochemical and behavioral characterization of novel methylphenidate analogs". The Journal of Pharmacology and Experimental Therapeutics 301 (2): 527–535.  
  4. ^ Davies, H.; Hopper, D.; Hansen, T.; Liu, Q.; Childers, S. (2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites". Bioorganic & Medicinal Chemistry Letters 14 (7): 1799–1802.