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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)

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