4-Fluoromethylphenidate (also known as 4-FMPH and 4F-MPH) is a

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

drug that acts as a higher potency

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dop ...

than the closely related

methylphenidate Methylphenidate, sold under the brand names Ritalin ( ) and Concerta ( ) among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It may be taken Oral adm ...

. 4-Fluoromethylphenidate was studied further along with other analogues of (±)-threo-methylphenidate (TMP) to assess their potential as anti-

cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...

medications. 4F-MPH was reported as having an ED₅₀ mg/kg of 0.26 (0.18–0.36), regarding its efficacy as a substitute for cocaine, and a relative potency of 3.33 compared to methylphenidate for the same purpose. This is based on its binding strength to the

dopamine transporter The dopamine transporter (DAT, also sodium-dependent dopamine transporter) is a membrane-spanning protein coded for in humans by the ''SLC6A3'' gene (also known as ''DAT1''), that pumps the neurotransmitter dopamine out of the synaptic cleft ba ...

vs. its activity as a

. In theory, this would block some of the effects of cocaine, without being as addictive. This has been misinterpreted as a dopamine vs.

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

selectivity ratio. Another study found that in the threo-isomers of methylphenidate, the

meta Meta most commonly refers to: * Meta (prefix), a common affix and word in English ( in Greek) * Meta Platforms, an American multinational technology conglomerate (formerly ''Facebook, Inc.'') Meta or META may also refer to: Businesses * Meta (ac ...

- and

para Para, or PARA, may refer to: Businesses, professions, and organizations * Paramount Global, traded as PARA on the Nasdaq stock exchange * Para Group, the former name of CT Corp * Para Rubber, now Skellerup, a New Zealand manufacturer * Para ...

-substituted compounds with electron-withdrawing substituents tended to have increased binding potency. Compounds containing

fluorine Fluorine is a chemical element; it has Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard temperature and pressure, standard conditions as pale yellow Diatomic molecule, diatomic gas. Fluorine is extre ...

chlorine Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...

bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...

and

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

groups were reported to be more potent than methylphenidate as well as the closely related compound

4F-EPH 4-Fluoroethylphenidate (4F-EPH) is a recreational designer drug from the phenidate family, with stimulant effects. It was first identified in France in March 2016. It has been used as a nootropic Nootropics ( or ) (colloquially brain supp ...

. 4F-MPH was reported as having the following values: sup>3H IN 35428 binding of 35.0 ± 3.0 (2) and sup>3Hopamine 142 ± 2.0 (2).

Legal status

4-Fluoromethylphenidate is a Schedule I controlled substance in the US state Alabama. As of 5 May 2017, 4-fluoromethylphenidate is a controlled substance in Canada.

References

{{DEFAULTSORT:Fluoromethylphenidate, 4- 2-Benzylpiperidines Carboxylate esters Designer drugs Methyl esters Norepinephrine–dopamine reuptake inhibitors Stimulants 2-Piperidinyl compounds

Legal status

See also

References