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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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.
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
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
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