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4-Methylmethylphenidate

From Wikipedia, the free encyclopedia
Stimulant drug

Pharmaceutical compound
4-Methylmethylphenidate
Legal status
Legal status
Identifiers
  • methyl (2R)-2-(4-methylphenyl)-2-[(2R)-piperidin-2-yl]acetate
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC15H21NO2
Molar mass247.338 g·mol−1
3D model (JSmol)
  • Cc2ccc(cc2)C(C(=O)OC)C1CCCCN1
  • InChI=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 checkY
  • Key:WJZNCJIOIACDBR-KBPBESRZSA-N checkY
  (verify)

threo-4-Methylmethylphenidate (4-MeTMP) is astimulant drug related tomethylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blockingdopaminereuptake despite its highbinding affinity, which led to its investigation as a possible substitute drug for treatment of stimulant abuse.[1] On the other hand, several other simple ring-substituted derivatives ofthreo-methylphenidate such as the 4-fluoro and 3-chloro compounds are more potent than methylphenidate both in efficacy asdopamine reuptake inhibitors and in animal drug discrimination assays.[2][3][4]

4-Fluoromethylphenidate (4F-MPH) and 3-chloromethylphenidate (3-CTMP)

Legality

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4-Methylmethylphenidate was banned in the UK as aTemporary Class Drug from June 2015 following its unapproved sale as adesigner drug.[5][6][7]

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

In the United States, on September 22, 2023, the DEA filed a proposed rule for placement ofethylphenidate 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

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References

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  1. ^Wayment HK, Deutsch H, Schweri MM, Schenk JO (March 1999)."Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists?".Journal of Neurochemistry.72 (3):1266–74.doi:10.1046/j.1471-4159.1999.0721266.x.PMID 10037500.
  2. ^Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM (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):1201–9.doi:10.1021/jm950697c.PMID 8632426.
  3. ^Schweri MM, Deutsch HM, Massey AT, Holtzman SG (May 2002). "Biochemical and behavioral characterization of novel methylphenidate analogs".The Journal of Pharmacology and Experimental Therapeutics.301 (2):527–35.doi:10.1124/jpet.301.2.527.PMID 11961053.
  4. ^Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR (April 2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites".Bioorganic & Medicinal Chemistry Letters.14 (7):1799–802.doi:10.1016/j.bmcl.2003.12.097.PMID 15026075.
  5. ^Methylphenidate-based NPS: A review of the evidence of use and harm. Advisory Council on the Misuse of Drugs, 31 March 2015
  6. ^"Letter to Mike Penning on methylphenidate-based novel psychoactive substances". Advisory Council on the Misuse of Drugs. 25 June 2015. Retrieved25 June 2015.
  7. ^"Ministerial response to the Advisory Council on the Misuse of Drugs about 2 new methylphenidate-based substances". Home Office. 25 June 2015. Retrieved25 June 2015.
  8. ^"Federal Register :: Request Access". 22 September 2023.
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