N-Methylephedrine

N-Methylephedrine is a derivative of ephedrine. It has been isolated from Ephedra distachya.[2]

N-Methylephedrine
Names
IUPAC name
(1R,2S)-2-(Dimethylamino)-1-phenyl-1-propanol
Other names
N-Methyl-L-ephedrine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.203
KEGG
UNII
  • InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1
    Key: FMCGSUUBYTWNDP-ONGXEEELSA-N
  • InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1
    Key: FMCGSUUBYTWNDP-ONGXEEELBH
  • O[C@H](c1ccccc1)[C@@H](N(C)C)C
Properties
C11H17NO
Molar mass 179.263 g·mol−1
Melting point 87 to 87.5 °C (188.6 to 189.5 °F; 360.1 to 360.6 K)[1]
192 °C (HCl)[1]
Readily soluble[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In organic chemistry, N-methylephedrine is used as a resolving agent and as a precursor to chiral supporting electrolytes, phase-transfer catalysts, and reducing agents.[3] Pharmacologically, N-methylephedrine is a non-selective adrenergic receptor agonist.[4]

Just like ephedrine, it may have abuse potential . N-methylephedrine is one of the four constituents of BRON, a Japanese OTC cough medicine with reports of abuse.[5] Addiction liability of BRON was attributed primarily to the Codeine component.

See also

References
  1. Merck Index, 11th Edition, 5987
  2. Smith (1927). "CCLXX. l-Methylephedrine, an alkaloid from Ephedra species". J. Chem. Soc.: 2056–2059. doi:10.1039/jr9270002056.
  3. (1R,2S)-(−)-N-Methylephedrine at Sigma-Aldrich
  4. "KEGG DRUG: dl-Methylephedrine hydrochloride". www.genome.jp. Retrieved 2023-01-12.
  5. Jun, Ishigooka; Yoshiko, Yoshida; Mitsukuni, Murasaki (1991-01-01). "Abuse of "BRON": A Japanese OTC cough suppressant solution containing methylephedrine, codeine, caffeine and chlorpheniramine". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 15 (4): 513–521. doi:10.1016/0278-5846(91)90026-W. ISSN 0278-5846. PMID 1749828. S2CID 53187238.


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