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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

Quality Level

200

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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