4-Fluoromethylphenidate

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4-Fluoromethylphenidate
4-Fluoromethylphenidate.png
Systematic (IUPAC) name
Methyl 2-(4-fluorophenyl)-2-(piperidin-2-yl)acetate
Identifiers
CAS Number 1354631-33-6
PubChem CID: 52944002
ChemSpider 26350585 YesY
Chemical data
Formula C14H18FNO2
Molecular mass 251.3 g/mol
  • FC1=CC=C(C=C1)C(C(=O)OC)C2CCCCN2
  • InChI=1S/C14H18FNO2/c1-18-14(17)13(12-4-2-3-9-16-12)10-5-7-11(15)8-6-10/h5-8,12-13,16H,2-4,9H2,1H3
  • Key:XISBAJBPDVRSPG-UHFFFAOYSA-N

4-Fluoromethylphenidate (also known as 4-FMPH and 4F-MPH) is a stimulant drug that acts as a higher efficiency dopamine reuptake inhibitor than the closely related methylphenidate.[1][2][3]

4-Fluoromethylphenidate was studied further along with other analogues of (±)-threo-methylphenidate (TMP) to assess their potential as anti-cocaine medications. 4-FTMP was reported as having an ED50 mg/kg of 0.26 (0.18–0.36) and a relative potency of 3.33 to Methylphenidate.[4]

Another study found that in the threo-isomers of methylphenidate, the meta- and para-substituted compounds with electron-withdrawing substituents tended to have increased binding potency. Compounds containing fluorine, chlorine, bromine and methyl groups were reported to be more potent than methylphenidate. 4-FTMP was reported as having the following values: [3H]WIN 35428 binding of 35.0 ± 3.0 (2) and [3H]dopamine 142 ± 2.0 (2).[5]

Legal Status

4-Fluoromethylphenidate is a Schedule I controlled substance in the US state Alabama.[6]

See also

References

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