4-Fluoromethylphenidate

4-Fluoromethylphenidate

Systematic (IUPAC) name
Methyl 2-(4-fluorophenyl)-2-(piperidin-2-yl)acetate
Identifiers
CAS Number	1354631-33-6
PubChem	CID 52944002
ChemSpider	26350585
Chemical data
Formula	C14H18FNO2
Molar mass	251.3 g/mol
SMILES FC1=CC=C(C=C1)C(C(=O)OC)C2CCCCN2
InChI 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

• 3,4-Dichloromethylphenidate
• 4-Methylmethylphenidate
• Dexmethylphenidate
• HDEP-28
• HDMP-28
• Isopropylphenidate
• Propylphenidate

References

1. Huw M.L. Davies, Darrin W. Hopper, Tore Hansen, Quixu Liu, Steven R. Childers (April 2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites". Bioorganic & Medicinal Chemistry Letters 14 (7): 1799–1802. doi:10.1016/j.bmcl.2003.12.097. PMID 15026075.
2. Milind Misra, Qing Shi, Xiaocong Ye, Ewa Gruszecka-Kowalik, Wei Bu, Zhanzhu Liu, Margaret M. Schweri, Howard M. Deutsch, Carol A. Venanzi (October 2010). "Quantitative structure–activity relationship studies of threo-methylphenidate analogs". Bioorganic & Medicinal Chemistry 18 (20): 7221–7238. doi:10.1016/j.bmc.2010.08.034. PMID 20846865.
3. Satendra Singh (February 2000). "Chemistry, Design, and Structure−Activity Relationship of Cocaine Antagonists". Chemical Reviews 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.
4. M. M. Schweri, H. M. Deutsch, A.T. Massey, S. G. Holtzman (May 2002). "Biochemical and Behavioral Characterization of Novel Methylphenidate Analogs". The Journal of Pharmacology and Experimental Therapeutics 301 (2): 527–535. doi:10.1124/jpet.301.2.527. PMID 11961053.
5. Howard M. Deutsch, Qing Shi, Ewa Gruszecka-Kowalik, Margaret M. Schweri (March 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.
6. "Alabama Senate Bill 333 - Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd.". March 2014. Retrieved 28 September 2015.