4-Methylmethylphenidate

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4-Methylmethylphenidate
4-methylmethylphenidate.png
Systematic (IUPAC) name
methyl (2R)-2-(4-methylphenyl)-2-[(2R)-piperidin-2-yl]acetate
Clinical data
Legal status
Identifiers
CAS Number 191790-79-1
680996-70-7 (hydrochloride)
PubChem CID: 44296147
ChemSpider 8281556 YesY
Chemical data
Formula C15H21NO2
Molecular mass 247.332 g/mol
  • 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 YesY
  • Key:WJZNCJIOIACDBR-KBPBESRZSA-N YesY
  (verify)

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]

4-fluoromethylphenidate (4-FTMP) and 3-chloromethylphenidate (3-CTMP)

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]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Methylphenidate-based NPS: A review of the evidence of use and harm. Advisory Council on the Misuse of Drugs, 31 March 2015
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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