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689661

Sigma-Aldrich

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

≥98.0% (NT)

Synonym(s):

(+)-Cathine, (+)-Pseudonorephedrine, (1S,2S)-2-Amino-1-phenyl-1-propanol, D-(+)-Norpseudoephedrine

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About This Item

CAS Number:
492-39-7
EC Number:
207-754-1
MDL number:
MFCD01711268
UNSPSC Code:
12352116
PubChem Substance ID:
329761281

Assay

≥98.0% (NT)

form

crystals

optical activity

[α]/D +34.0±2.0°, c = 3.5 in ethanol

drug control

USDEA Schedule IV; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIB (Portugal)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1

InChI key

DLNKOYKMWOXYQA-IONNQARKSA-N

Application

(1S,2S)-(+)-Norpseudoephedrine can be used:
  • As a starting material for the synthesis of benzamide based ligands applicable in the Tsuji−Trost allylic alkylation reactions.
  • To prepare its catalyst derivatives, which are applicable in the alkylation of benzaldehydes using diethylzinc.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

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)

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β-Amino alcohols derived from (1R,2S)-norephedrine and (1S, 2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes
Parrott II, et al.
Tetrahedron Asymmetry, 19(1), 19-26 (2008)
β-Hydroxy and β-(o-diphosphino) benzoyloxy (o-diphosphino) benzamides as ligands for asymmetric allylic alkylation
Mahadik GS, et al.
Tetrahedron Asymmetry, 20(10), 1132-1137 (2009)
Kuei Hui Chan et al.
Journal of analytical toxicology, 33(3), 162-166 (2009-04-18)
Sho-seiryu-to is one of the most common Traditional Chinese Medicine preparations for the attenuation of colds. Ephedrae Herba is one of the prescriptions of Sho-seiryu-to. The major ingredients of Ephedrae Herba, ephedrines, are banned substances on the World Anti-Doping Agency
Ying Shi et al.
Journal of chromatography. A, 1218(42), 7655-7662 (2011-09-09)
A method for simultaneous determination of eight adulterants including two appetite suppressants, two energy expenditure-enhancing drugs, one diuretic and three cathartics in slimming functional foods by high performance liquid chromatography with electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) was established. After samples
Toshiaki Nagai et al.
Journal of analytical toxicology, 36(2), 96-105 (2012-02-18)
A method for identifying the enantiomers of N,O-di-trifluoroacetylated ephedrine (EP) and norephedrine (NE) and the enantiomers of pseudoephedrine (PEP) and pseudonorephedrine (PNE) in plasma was developed using chiral capillary gas chromatography-mass spectrometry (GC-MS) with selected ion monitoring (SIM). N,O-Di-trifluoroacethyl (TFA)
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