287636
(1S,2S)-(+)-Pseudoephedrine
98%
Synonym(s):
(+)-Pseudoephedrine, (+)-ψ-Ephedrine, (1S,2S)-2-Methylamino-1-phenyl-1-propanol, d-Isoephedrine, d-Pseudoephedrine
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About This Item
Empirical Formula (Hill Notation):
C10H15NO
CAS Number:
Molecular Weight:
165.23
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-018-6
Beilstein/REAXYS Number:
2414132
MDL number:
assay
98%
form
solid
optical activity
[α]20/D +52°, c = 0.6 in ethanol
mp
118-120 °C
functional group
amine, hydroxyl, phenyl
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-WCBMZHEXSA-N
General description
(1S,2S)-(+)-Pseudoephedrine, a natural enantiomer of ephedrine, is a decongestant commonly used in cold and allergy medicines.
Application
(1S,2S)-(+)-Pseudoephedrine condenses with N,N-diisopropyl-2-formyl-1-naphthamide to form the corresponding oxazolidine derivative as a single diasterisomer.
(1S,2S)-(+)-Pseudoephedrine may be used as a chiral auxillary in asymmetric synthesis of enantioenriched organic compounds. It may also be used to prepare a novel tertiary pseudo C2-symmetric 1,2-diamine, which facilitates the enantioselective addition of methyl lithium to imines with better yield.
Biochem/physiol Actions
Non-selective adrenergic agonist; decongestant
signalword
Warning
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
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
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Jillian M Hagel et al.
Trends in plant science, 17(7), 404-412 (2012-04-17)
Amphetamine analogs are produced by plants in the genus Ephedra and by Catha edulis, and include the widely used decongestants and appetite suppressants pseudoephedrine and ephedrine. A combination of yeast (Candida utilis or Saccharomyces cerevisiae) fermentation and subsequent chemical modification
(-)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control.
Clayden J and Lai LW.
Tetrahedron Letters, 42(18), 3163-3166 (2001)
A new pseudo C2-symmetric tertiary diamine for the enantioselective addition of MeLi to aromatic imines.
Gille S, et al.
Tetrahedron Asymmetry, 17(7), 1045-1047 (2006)