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235210

Sigma-Aldrich

(1R,2S)-(−)-N-Methylephedrine

99%

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Synonym(s):
(−)-(1R,2S)-2-Dimethylamino-1-phenylpropanol, (−)-N-Methylephedrine, [R-(R*,S*)]-α-[1-(Dimethylamino)ethyl]benzenemethanol
Linear Formula:
C6H5CH(OH)CH(CH3)N(CH3)2
CAS Number:
Molecular Weight:
179.26
Beilstein/REAXYS Number:
3031197
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
134910862231287776
(1R,2S)-(−)-N-Methylephedrine 99%

235210

(1R,2S)-(−)-N-Methylephedrine

(1R,2S)-(−)-Ephedrine 98%

134910

(1R,2S)-(−)-Ephedrine

(1S,2R)-(+)-N-Methylephedrine 99%

287776

(1S,2R)-(+)-N-Methylephedrine

form

solid

form

solid

form

crystals

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

mp

86-88 °C (lit.)

mp

37-39 °C (lit.)

mp

216-220 °C (lit.)

mp

87-90 °C (lit.)

optical activity

[α]21/D −29.2°, c = 5 in methanol

optical activity

[α]21/D −41°, c = 5 in 1 M HCl

optical activity

[α]20/D −34°, c = 4 in H2O

optical activity

[α]20/D +29°, c = 5 in methanol

Application

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Angewandte Chemie (International Edition in English), 23, 165-165 (1984)
Chemistry Letters (Jpn), 981-981 (1980)
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
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
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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