4-Methylmethylphenidate Explained

Verifiedrevid:	421303810
Iupac Name:	methyl (2R)-2-(4-methylphenyl)-2-[(2''R'')-piperidin-2-yl]acetate
Width:	200px
Legal Ca:	Schedule III
Legal De:	NpSG
Legal Uk:	Class B
Cas Number:	191790-79-1
Unii:	1Y11XUO4EY
Cas Supplemental:	680996-70-7 (hydrochloride)
Pubchem:	44296147
Chemspiderid:	8281556
C:	15
H:	21
N:	1
O:	2
Smiles:	Cc2ccc(cc2)C(C(=O)OC)C1CCCCN1
Stdinchi:	1S/C15H21NO2/c1-11-6-8-12(9-7-11)14(15(17)18-2)13-5-3-4-10-16-13/h6-9,13-14,16H,3-5,10H2,1-2H3/t13-,14-/m0/s1
Stdinchikey:	WJZNCJIOIACDBR-KBPBESRZSA-N

threo-4-Methylmethylphenidate (4-MeTMP) is a stimulant drug related to methylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking dopamine reuptake despite its high binding affinity, which led to its investigation as a possible substitute drug for treatment of stimulant abuse (cf. nocaine).^[1] 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 inhibitors and in animal drug discrimination assays.^{[2] [3] [4]}

Legality

4-Methylmethylphenidate was banned in the UK as a Temporary Class Drug from June 2015 following its unapproved sale as a designer drug.^{[5] [6] [7]}

In the United States, 4-methylmethylphenidate may be considered illegal if intended for human consumption under the federal analogue act as a structural analog of methylphenidate.

In the United States, on September 22, 2023, the DEA filed a proposed rule for placement of ethylphenidate 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.^[8]

See also

• 3-Bromomethylphenidate
• 3,4-Dichloromethylphenidate
• 4-Fluoromethylphenidate
• 4-Methylphenmetrazine
• Dexmethylphenidate
• HDMP-28
• Isopropylphenidate
• Propylphenidate

Notes and References

1. Wayment HK, Deutsch H, Schweri MM, Schenk JO . Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists? . Journal of Neurochemistry . 72 . 3 . 1266–74 . March 1999 . 10037500 . 10.1046/j.1471-4159.1999.0721266.x . free .
2. Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM . Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs . Journal of Medicinal Chemistry . 39 . 6 . 1201–9 . March 1996 . 8632426 . 10.1021/jm950697c .
3. Schweri MM, Deutsch HM, Massey AT, Holtzman SG . Biochemical and behavioral characterization of novel methylphenidate analogs . The Journal of Pharmacology and Experimental Therapeutics . 301 . 2 . 527–35 . May 2002 . 11961053 . 10.1124/jpet.301.2.527 .
4. Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR . Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites . Bioorganic & Medicinal Chemistry Letters . 14 . 7 . 1799–802 . April 2004 . 15026075 . 10.1016/j.bmcl.2003.12.097 .
5. https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/420983/TCDO_methylphenidate_NPS.pdf Methylphenidate-based NPS: A review of the evidence of use and harm. Advisory Council on the Misuse of Drugs, 31 March 2015
6. Web site: Letter to Mike Penning on methylphenidate-based novel psychoactive substances . Advisory Council on the Misuse of Drugs . 25 June 2015 . 25 June 2015.
7. Web site: Ministerial response to the Advisory Council on the Misuse of Drugs about 2 new methylphenidate-based substances . Home Office . 25 June 2015 . 25 June 2015.
8. Web site: Federal Register :: Request Access .