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Updating {{drugbox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:WikiProject
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{{Drugbox
{{Drugbox
| verifiedrevid = 399304572
| verifiedrevid = 443273932
| IUPAC_name = methyl (2''R'')-2-(3,4-dichlorophenyl)-2-[(2''R'')-piperidin-2-yl]acetate
| IUPAC_name = methyl (2''R'')-2-(3,4-dichlorophenyl)-2-[(2''R'')-piperidin-2-yl]acetate
| image = Dichloromethylphenidate.png
| image = Dichloromethylphenidate.png

Revision as of 18:51, 10 September 2011

3,4-Dichloromethylphenidate
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: unscheduled
Identifiers
  • methyl (2R)-2-(3,4-dichlorophenyl)-2-[(2R)-piperidin-2-yl]acetate
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H17Cl2NO2
Molar mass302.196 g/mol g·mol−1
3D model (JSmol)
  • N2CCCCC2C(C(=O)OC)c(cc1Cl)ccc1Cl
  • InChI=1S/C14H17Cl2NO2.ClH/c1-19-14(18)13(12-4-2-3-7-17-12)9-5-6-10(15)11(16)8-9;/h5-6,8,12-13,17H,2-4,7H2,1H3;1H/p-1/t12-,13+;/m1./s1 checkY
  • Key:DJQISAOWJXQDPU-KZCZEQIWSA-M checkY
  (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. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8632426, please use {{cite journal}} with |pmid=8632426 instead.
  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 medicinal 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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