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287636 Sigma-Aldrich

(1S,2S)-(+)-Pseudoephedrine

98%

Synonym: (+)-ψ-Ephedrine, (+)-Pseudoephedrine, (1S,2S)-2-Methylamino-1-phenyl-1-propanol, d-Isoephedrine, d-Pseudoephedrine

  • CAS Number 90-82-4

  • Empirical Formula (Hill Notation) C10H15NO

  • Molecular Weight 165.23

  •  Beilstein/REAXYS Number 2414132

  •  EC Number 202-018-6

  •  MDL number MFCD00064256

  •  PubChem Substance ID 24857282

  •  NACRES NA.22

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Properties

Related Categories Alkaloid, Asymmetric Synthesis, Cell Biology, Chemical Synthesis, Chiral Auxiliaries,
Quality Level   100
assay   98%
optical activity   [α]20/D +52°, c = 0.6 in ethanol
mp   118-120 °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-WCBMZHEXSA-N

Description

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.

Packaging

5, 25, 100 g in glass bottle

Biochem/physiol Actions

Non-selective adrenergic agonist; decongestant

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UL5800000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Ephedrines

Both enantiomers of ephedrine, pseudoephedrine, norephedrine, and their derivatives are used as practical chiral auxiliaries for asymmetric synthesis. Enolates of readily available (1R,2R)-(–)- and (...
Aldrich ChemFiles 2005, 5.4, 9.
Keywords: Alkylations, Asymmetric synthesis, Chemfiles, Chiral auxiliaries

HPLC Analysis of Cold Remedy Components on Ascentis® Express 2.0 μm RP-Amide

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Cold Remedy Components on Ascentis® Express 2.0 μm RP-Amide
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical, Separation

HPLC Analysis of Pseudoephedrine Enantiomers on Astec® CHIROBIOTIC® T

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Pseudoephedrine Enantiomers on Astec® CHIROBIOTIC® T
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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