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Merck
CN

134910

(1R,2S)-(−)-Ephedrine

98%

Synonym(s):

(−)-Ephedrine, (1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (1R,2S)-(−)-2-Methylamino-1-phenyl-1-propanol, L-α-(1-Methylaminoethyl)benzyl alcohol

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About This Item

Linear Formula:
C6H5CH[CH(NHCH3)CH3]OH
CAS Number:
299-42-3
Molecular Weight:
165.23
Beilstein:
2208730
EC Number:
206-080-5
MDL number:
MFCD00064257
UNSPSC Code:
12352116
PubChem Substance ID:
24848190
NACRES:
NA.22

Key Documents

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Quality Level

200

Assay

98%

form

solid

optical activity

[α]21/D −41°, c = 5 in 1 M HCl

bp

255 °C (lit.)

mp

37-39 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

functional group

amine
hydroxyl
phenyl

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

InChI key

KWGRBVOPPLSCSI-WPRPVWTQSA-N

Related Categories

General description

(1R,2S)-(-)-Ephedrine, a chiral β-amino alcohol, is commonly used as a chiral auxiliary in asymmetric synthesis. It undergoes reduction to form (+)-methamphetamine.

Application

(1R,2S)-(-)-Ephedrine can be used in the preparation of optically active phosphine-phosphonite ligands and chirally-substituted cyclopentadienyl (Cp) ligands. It reacts with phosphorus trichloride to form (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine. It can also act as a chiral resolving agent for (±)-mandelic acid.
Versatile chiral synthon, employed in catalysis and in the preparation of optically pure sulfoxides and oxazolidines.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7974
STBG4818V
STBG2435V
STBF3993V
STBF0862V

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A L Carey et al.
Diabetologia, 56(1), 147-155 (2012-10-16)
Brown adipose tissue (BAT) activation increases energy consumption and may help in the treatment of obesity. Cold exposure is the main physiological stimulus for BAT thermogenesis and the sympathetic nervous system, which innervates BAT, is essential in this process. However
A novel nucleoside phosphoramidite synthon derived from 1R, 2S-ephedrine
Iyer RP, et al
Tetrahedron Asymmetry, 6(5), 1051-1054 (1995)
Enantiomeric Resolution of (?)-Mandelic Acid by (1R, 2S)-(-)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism
Baar MR and Cerrone-Szakal AL
Journal of Chemical Education, 82(7), 1040-1040 (2005)
Investigation of (1R, 2S)-(-)-Ephedrine by Cryogenic Terahertz Spectroscopy and Solid-State Density Functional Theory.
Hakey PM, et al
ChemPhysChem, 10(14), 2434-2444 (2009)
Penelope P Howards et al.
PloS one, 7(11), e50372-e50372 (2012-11-21)
Medications may be consumed periconceptionally before a woman knows she is pregnant. In this study, the authors evaluate the association of a prescription diet drug (Letigen) containing ephedrine (20 mg) and caffeine (200 mg) with spontaneous abortion (SAB) in the
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