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Merck
CN

235210

(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
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
24854088
EC Number:
209-022-7
Beilstein/REAXYS Number:
3031197
MDL number:
MFCD00004504

Key Documents

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InChI key

FMCGSUUBYTWNDP-ONGXEEELSA-N

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

SMILES string

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

assay

99%

form

solid

optical activity

[α]21/D −29.2°, c = 5 in methanol

mp

86-88 °C (lit.)

functional group

amine, hydroxyl, phenyl

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL4243V
BCBB0985V
BCBB0985
1346683
1133031

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Chemistry Letters (Jpn), 981-981 (1980)
Angewandte Chemie (International Edition in English), 23, 165-165 (1984)
María José Ojeda-Montes et al.
Future medicinal chemistry, 9(18), 2129-2146 (2017-11-28)
Extracts from Ephedra species have been reported to be effective as antidiabetics. A previous in silico study predicted that ephedrine and five ephedrine derivatives could contribute to the described antidiabetic effect of Ephedra extracts by inhibiting dipeptidyl peptidase IV (DPP-IV).
Guoyi Ma et al.
The Journal of pharmacology and experimental therapeutics, 322(1), 214-221 (2007-04-05)
Ephedra species of plants have both beneficial and adverse effects primarily associated with the presence of ephedrine alkaloids. Few reports have appeared that examine the direct actions of ephedrine alkaloids on human subtypes of adrenergic receptors (ARs). In the present
H J Lee et al.
Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology, 30(6), 563-566 (2010-08-13)
No information is currently available on the safety of methylephedrine, a component of various cold medications available in South Korea. With previous approval by an Institutional Review Board, 349 women inadvertently exposed to methylephedrine during the 1st trimester of pregnancy
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