3,4-Dichloromethylphenidate

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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
CAS Number
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
 ☒NcheckY (what is this?)  (verify)

3,4-Dichloromethylphenidate is a stimulant drug related to methylphenidate.

Dichloromethylphenidate is a potent psychostimulant that acts as both a dopamine reuptake inhibitor and norepinephrine reuptake inhibitor, meaning it effectively boosts the levels of the norepinephrine and dopamine neurotransmitters in the brain, by binding to, and partially blocking the transporter proteins that normally remove those monoamines from the synaptic cleft

The threo-diastereomer (3,4-CTMP) is approximately seven times 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]

3,4-Dichloromethylphenidate has been seen since 2013 on the UK legal high and research chemical markets.[7]

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 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
  7. ^ 3,4-CTMP Thread at UKChemicalResearch.org


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