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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

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

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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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
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
(-)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control.
Clayden J and Lai LW.
Tetrahedron Letters, 42(18), 3163-3166 (2001)
A new pseudo C2-symmetric tertiary diamine for the enantioselective addition of MeLi to aromatic imines.
Gille S, et al.
Tetrahedron Asymmetry, 17(7), 1045-1047 (2006)
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)
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