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235210

Sigma-Aldrich

(1R,2S)-(−)-N-Methylephedrine

99%

Synonym(s):

(−)-(1R,2S)-2-Dimethylamino-1-phenylpropanol, (−)-N-Methylephedrine, [R-(R*,S*)]-α-[1-(Dimethylamino)ethyl]benzenemethanol

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About This Item

Linear Formula:
C6H5CH(OH)CH(CH3)N(CH3)2
CAS Number:
552-79-4
Molecular Weight:
179.26
Beilstein:
3031197
EC Number:
209-022-7
MDL number:
MFCD00004504
UNSPSC Code:
12352116
PubChem Substance ID:
24854088
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]21/D −29.2°, c = 5 in methanol

mp

86-88 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H]([C@H](O)c1ccccc1)N(C)C

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

InChI key

FMCGSUUBYTWNDP-ONGXEEELSA-N

Application

Resolving agent. Precursor to chiral supporting electrolytes, phase-transfer catalysts, and reducing agents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Angewandte Chemie (International Edition in English), 23, 165-165 (1984)
Chemistry Letters (Jpn), 981-981 (1980)
Satoshi Murao et al.
Internal medicine (Tokyo, Japan), 47(11), 1013-1015 (2008-06-04)
We report a 35-year-old man who was referred to our hospital with generalized convulsion and mixed acidosis presumably caused by abuse of SS-BRON tablets, an over-the-counter (OTC) antitussive medication sold in Japan. These tablets contain dihydrocodeine phosphate, methylephedrine, chlorpheniramine, and
Jingguo Hou et al.
Electrophoresis, 28(9), 1352-1363 (2007-05-01)
In this work, simultaneous separation of eight stereoisomers of ephedrine and related compounds ((+/-)-ephedrine, (+/-)-pseudoephedrine, (+/-)-norephedrine and (+/-)-N-methylephedrine) was accomplished using a polymeric chiral surfactant, i.e. polysodium N-undecenoxycarbonyl-L-leucinate (poly-L-SUCL) by chiral (C)MEKC-ESI-MS. The conditions of CMEKC were first investigated. The
Kathlyn A Parker et al.
Organic letters, 10(7), 1349-1352 (2008-03-05)
A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one
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