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3,4-Dichloromethylphenidate

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3,4-Dichloromethylphenidate

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3,4-Dichloromethylphenidate
Systematic (IUPAC) name
methyl (2R)-2-(3,4-dichlorophenyl)-2-[(2R)-piperidin-2-yl]acetate
Clinical data
Pregnancy cat.  ?
Legal status Unscheduled
Routes Oral
Identifiers
ATC code None
PubChem CID 44296390
ChemSpider 23104857 YesY
Chemical data
Formula C14H17Cl2NO2 
Mol. mass 302.196 g/mol
SMILES eMolecules & PubChem
 YesY (what is this?)  (verify)

threo-3,4-Dichloromethylphenidate (3,4-CTMP) is a stimulant drug related to methylphenidate. It is around 7x more potent than methylphenidate in animal studies, but has weaker reinforcing effects due to its slower onset of action.[1][2][3][4][5] However, H. M. Deutsch's discrimination ratio implies it to be more addictive than even cocaine.[6]

See also

References

  1. ^ 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". Journal of Medicinal Chemistry 39 (6): 1201–1209. doi:10.1021/jm950697c. PMID 8632426.  edit
  2. ^ Wayment, HK; Deutsch, H; Schweri, MM; Schenk, JO (1999). "Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists?". Journal of Neurochemistry 72 (3): 1266–74. doi:10.1046/j.1471-4159.1999.0721266.x. PMID 10037500. 
  3. ^ Schweri, MM; Deutsch, HM; Massey, AT; Holtzman, SG (2002). "Biochemical and behavioral characterization of novel methylphenidate analogs". The Journal of Pharmacology and Experimental Therapeutics 301 (2): 527–35. doi:10.1124/jpet.301.2.527. PMID 11961053. 
  4. ^ Davies, HM; Hopper, DW; Hansen, T; Liu, Q; Childers, SR (2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites". Bioorganic & Medicinal Chemistry Letters 14 (7): 1799–802. doi:10.1016/j.bmcl.2003.12.097. PMID 15026075. 
  5. ^ Kim, DI; Deutsch, HM; Ye, X; Schweri, MM (2007). "Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate". Journal of Medical Chemistry 50 (11): 2718–31. doi:10.1021/jm061354p. PMID 17489581. 
  6. ^ Schweri MM, Deutsch HM, Massey AT, Holtzman SG. Biochemical and behavioral characterization of novel methylphenidate analogs. J Pharmacol Exp Ther. 2002 May;301(2):527-35. DOI|10.1124/jpet.301.2.527 PMID 11961053


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