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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.[1]
  • To prepare its catalyst derivatives, which are applicable in the alkylation of benzaldehydes using diethylzinc.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBK7045V
BCBF9322V
1351588

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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)
John S Chappell et al.
Forensic science international, 195(1-3), 108-120 (2009-12-29)
A primary concern with the forensic analysis of the khat plant (Catha edulis) has been the need to preserve the principle psychoactive component, cathinone, which converts to the less-active substance, cathine, after harvesting. The loss of cathinone has serious legal
Hyeon-Kyu Lee et al.
The Journal of organic chemistry, 77(12), 5454-5460 (2012-05-25)
Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO(2)H/Et(3)N as
Carlos Castillo-Henkel et al.
Proceedings of the Western Pharmacology Society, 53, 33-36 (2010-01-01)
Here we contrast the vascular smooth muscle contractility produced by D-nor-pseudoephedrine, alone or combined with triiodothyronine, on the aorta and coronary vasculature of the rat. At high concentrations (greater than those found in normal therapeutic dosing) D-nor-pseudoephedrine contracted the aorta.
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