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Chemicals List 1 >> N-methylpseudoephedrine
N-methylpseudoephedrine
CAS number 51018-28-1
Synonyms: (+)-N-Methylpseudoephedrine,
(1S,2S)-2-Dimethylamino-1-phenylpropanol
CAS
Number: 51018-28-1
Linear Formula: C6H5CH[CH(CH3)N(CH3)2]OH
Molecular Weight: 179.26
MDL number: MFCD00064260
PubChem Substance ID: 24857422
Properties
assay 99%
optical activity [α]21/D +48°, c = 5 in methanol
bp 145 °C/24 mmHg(lit.)
mp 29-31 °C(lit.)
Safety
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36
WGK Germany 3
Flash Point(F) 235 °F
Flash Point(C) 113 °C
Abstract
Treatment of (Image )-(η6-Image ,Image -dimethylamphetamine)Cr(CO)3,
with Image -butyllithium below -40°C gives a stable benzylic
carbanion Image loss of the Image -Image -benzylic proton. Warming
of this anion above -40°C gives (η6-Image -β-methylstyrene)Cr(CO)3
Image an ElcB type elimination whilst trapping with an electrophile
below -40°C gives benzylically functionalised amphetamines with
overall retention of configuration.
The use of oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide as
the electrophile gives optically pure (Image ,Image )-Image -methylpseudoephedrine
after decomplexation.
N-methylpseudoephedrineis a sympathomimetic agent, structurally
similar to ephedrine, used to relieve nasal and sinus congestion and
reduce air-travel-related otalgia in adults.
The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate
are found in many over-the-counter preparations either as
single-ingredient preparations, or more commonly in combination with
antihistamines and/or paracetamol/ibuprofen.
Unlike antihistamines, which modify the systemic histamine-mediated
allergic response, pseudoephedrine only serves to relieve nasal
congestion commonly associated with colds or allergies.
The advantage of oral pseudoephedrine over topical nasal
preparations, such as oxymetazoline, is that it does not cause
rebound congestion.
N-methylpseudoephedrineis acts directly on both alpha- and, to a
lesser degree, beta-adrenergic receptors.
Through direct action on alpha-adrenergic receptors in the mucosa of
the respiratory tract, pseudoephedrine produces vasoconstriction.
Pseudoephedrine relaxes bronchial smooth muscle by stimulating
beta2-adrenergic receptors.
Like ephedrine, pseudoephedrine releasing norepinephrine from its
storage sites, an indirect effect.
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