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287636

Sigma-Aldrich

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

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H15NO
CAS Number:
90-82-4
Molecular Weight:
165.23
Beilstein:
2414132
EC Number:
202-018-6
MDL number:
MFCD00064256
UNSPSC Code:
12352116
PubChem Substance ID:
24857282
NACRES:
NA.22

Quality Level

100

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

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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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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
0001451675
SLBX8035
SLBR0233V
SLBP0095V
1451675V

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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
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)
Beatriz Alonso et al.
The Journal of organic chemistry, 78(2), 614-627 (2012-12-25)
We have developed an efficient protocol for carrying out the stereocontrolled formal conjugate addition of hydroxycarbonyl anion equivalents to α,β-unsaturated carboxylic acid derivatives using (S,S)-(+)-pseudoephedrine as chiral auxiliary, making use of the synthetic equivalence between the heteroaryl moieties and the
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
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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