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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
Related Categories
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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Pseudoephenamine: a practical chiral auxiliary for asymmetric synthesis.
Marvin R Morales et al.
Angewandte Chemie (International ed. in English), 51(19), 4568-4571 (2012-03-31)
Wayland Hsiao et al.
BJU international, 110(8), 1196-1200 (2012-01-12)
What's known on the subject? and What does the study add? Modern surgical techniques have allowed preservation of fertility in most patients after post-chemotherapy retroperitoneal lymph node dissection (PC-RPLND), but some patients still have infertility after surgery. We reviewed our
James K Cunningham et al.
Drug and alcohol dependence, 126(1-2), 55-64 (2012-05-18)
Clandestine laboratory operators commonly extract ephedrine and pseudoephedrine-precursor chemicals used to synthesize methamphetamine-from over-the-counter cold/allergy/sinus products. To prevent this activity, two states, Oregon in 07/2006 and Mississippi in 07/2010, implemented regulations classifying ephedrine and pseudoephedrine as Schedule III substances, making
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
A Antony Muthu Prabhu et al.
Journal of fluorescence, 22(6), 1461-1474 (2012-07-04)
The absorption and fluorescence spectra of labetalol and pseudoephedrine have been studied in different polarities of solvents and β-cyclodextrin (β-CD). The inclusion complexation with β-CD is investigated by UV-visible, steady state and time resolved fluorescence spectra and PM3 method. In
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