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''threo''-4-Methylmethylphenidate (4-MeTMP) 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 related to
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 ...
. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking
dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...
reuptake Reuptake is the reabsorption of a neurotransmitter by a neurotransmitter transporter located along the plasma membrane of an axon terminal (i.e., the pre-synaptic neuron at a synapse) or glial cell after it has performed its function of transmi ...
despite its high
binding affinity In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from Latin ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usuall ...
, which led to its investigation as a possible substitute drug for treatment of stimulant abuse (cf.
nocaine (+)-CPCA (nocaine, 3α-carbomethoxy-4β-(4-chlorophenyl)-''N''-methylpiperidine aka CTDP 31,446) is a stimulant drug similar in structure to pethidine (an opioid that possesses NDRI actions) and to RTI-31, but nocaine lacks the two-carbon brid ...
). On the other hand, several other simple ring-substituted derivatives of ''threo''-methylphenidate such as the 4-fluoro and 3-chloro compounds are more potent than methylphenidate both in efficacy as
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 ...
s and in animal drug discrimination assays.


Legality

4-Methylmethylphenidate was banned in the UK as a
Temporary Class Drug A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The contro ...
from June 2015 following its unapproved sale as a
designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...
. In the United States, 4-methylmethylphenidate may be considered illegal if intended for human consumption under the
federal analogue act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...
as a structural analog of methylphenidate. In the United States, on September 22, 2023, the DEA filed a proposed rule for placement of
ethylphenidate Ethylphenidate (EPH) is a central nervous system (CNS) stimulant and a close analog of methylphenidate. Ethylphenidate acts as a norepinephrine–dopamine reuptake inhibitor, meaning it effectively boosts the levels of the norepinephrine and do ...
into Schedule I status, which would include its isomers. 4-Methylmethylphenidate is a positional isomer of ethylphenidate and thus the scheduling of ethylphenidate into Schedule I status would cause 4-methylmethylphenidate to be a Schedule I substance as well.


See also

*
3-Bromomethylphenidate 3-Bromomethylphenidate (3-Br-MPH) is a compound from the phenidate family, which has reportedly been sold as a designer drug. It showed the most potent binding to the dopamine transporter of a series of ring-substituted methylphenidate derivative ...
*
3,4-Dichloromethylphenidate 3,4-dichloromethylphenidate (abbreviated as 3,4-DCMP, and incorrectly as 3,4-CTMP for the d,l-threo diastereomer) is a potent stimulant drug from the List of methylphenidate analogues, phenidate class closely related to methylphenidate. It acts ...
* 4-Fluoromethylphenidate * 4-Methylphenmetrazine *
Dexmethylphenidate Dexmethylphenidate, sold under the brand name Focalin among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) in those over the age of five years. It is taken by mouth. ...
*
HDMP-28 HDMP-28 or methylnaphthidate is a stimulant drug of the piperidine and naphthylaminopropane groups, closely related to methylphenidate (Ritalin), but with the benzene ring replaced by naphthalene. It is a potent dopamine reuptake inhibitor, wit ...
*
Isopropylphenidate Isopropylphenidate (also known as IPH and IPPD) is a piperidine based stimulant drug, closely related to methylphenidate, but with the methyl ester replaced by an isopropyl ester. It has similar effects to methylphenidate but with a longer durat ...
*
Propylphenidate Propylphenidate (also known as PPH) is a piperidine based stimulant drug, closely related to methylphenidate, but with the methyl ester replaced by a propyl ester. It was banned in the UK as a Temporary Class Drug from April 2015 following its u ...


References

{{DEFAULTSORT:Methylmethylphenidate, 4- Stimulants Designer drugs 2-Benzylpiperidines Methyl esters Carboxylate esters 2-Piperidinyl compounds