O-2172

O-2172
Identifiers
IUPAC name
  • methyl 2-cyclopentyl-2-(3,4-dichlorophenyl)acetate
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H16Cl2O2
Molar mass287.18 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1Cl)C(C(=O)OC)C2CCCC2
InChI
  • InChI=1S/C14H16Cl2O2/c1-18-14(17)13(9-4-2-3-5-9)10-6-7-11(15)12(16)8-10/h6-9,13H,2-5H2,1H3 ☒N
  • Key:NEHPFNBRZYFWFN-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

O-2172 is a drug developed by Organix Inc, which acts as a stimulant and potent dopamine reuptake inhibitor. It is an analogue of methylphenidate where the phenyl ring has had a 3,4-dichloro substitution added, and the piperidine ring has been replaced by cyclopentane. It is around 1/3 the potency of methylphenidate, demonstrating that even with the important binding group of the nitrogen lone pair removed entirely, selective DAT binding and reuptake inhibition is still possible.[1][2]

See also

References

  1. ↑ Meltzer PC, Wang P, Blundell P, Madras BK (April 2003). "Synthesis and evaluation of dopamine and serotonin transporter inhibition by oxacyclic and carbacyclic analogues of methylphenidate". Journal of Medicinal Chemistry. 46 (8): 1538–45. doi:10.1021/jm0205292. PMID 12672255.
  2. ↑ Runyon SP, Carroll FI (2006). "Dopamine transporter ligands: recent developments and therapeutic potential". Current Topics in Medicinal Chemistry. 6 (17): 1825–43. doi:10.2174/156802606778249775. PMID 17017960.
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