14222-20-9

Basic information

• Product Name: (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE
• Synonyms: (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE;(-)-N-Methyl-y-ephedrine;(R,R)-N-Methylpseudoephedrine;Benzenemethanol, α-[(1R)-1-(dimethylamino)ethyl]-, (αR)-;Benzenemethanol, α-[1-(dimethylamino)ethyl]-, [R-(R*,R*)]-;Benzyl alcohol, α-[1-(dimethylamino)ethyl]-, (-)- (8CI);D-(-)-threo-Methylephedrine;D-(-)-threo-N-Methylephedrine
• CAS NO: 14222-20-9
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.25878
• Mol File: 14222-20-9.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 251.3°Cat760mmHg
• Flash Point: 96.9°C
• Appearance: /
• Density: 1.009g/cm³
• Vapor Pressure: 0.0108mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE(14222-20-9)
• EPA Substance Registry System: (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE(14222-20-9)

Safety Data

• Hazardous Substances Data: 14222-20-9(Hazardous Substances Data)

Usage

General Description

(1R,2R)-(-)-N-Methylpseudoephedrine is a chiral compound and a diastereomer of ephedrine. It is a psychostimulant and sympathomimetic amine with structural similarities to the neurotransmitter epinephrine. (1R,2R)-(-)-N-METHYLPSEUDOEPHEDRINE has been used as a decongestant and for its stimulant effects, although its use has been largely replaced by other pharmaceuticals due to its potential for abuse and the development of safer alternatives. It is also structurally similar to the banned drug methamphetamine and its use is regulated in many countries. Despite this, it is still used in some over-the-counter medications for the treatment of nasal congestion and is also of interest in the development of novel pharmaceuticals.

InChI:InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11+/m1/s1

Upstream product

• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 17279-39-9 (S)-N,N-dimethyl-α-benzylethylamine 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 
• 66574-19-4 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidine 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 130459-53-9 (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol 
• 15351-09-4 metamfepramone 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 153360-78-2 ((1R,2R)-2-chloro-1-methyl-2-phenyl-ethyl)-dimethyl-amine; hydrochloride 
• 65528-82-7 (R)-2-(dimethylamino)propiophenone 

Downstream Products

• 128510-49-6 ((1R,2S)-2-chloro-1-methyl-2-phenyl-ethyl)-dimethyl-amine 
• 128510-47-4 ((1R,2R)-2-chloro-1-methyl-2-phenyl-ethyl)-dimethyl-amine 
• 57155-63-2 (+)-(1S,2S)-N-dodecyl-N,N-dimethylpseudoephedrinium bromide 
• 158837-63-9 (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane 
• 129216-60-0 lithium N-methylpseudoephedrate 
• 74059-55-5 (1S,2S)-N-methyl-ψ-ephedrine propionate 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 4436-22-0 (2S,3R)-2-methyl-3-phenyloxirane 
• 50-00-0 formaldehyd 
• 90-81-3 ephedrine 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 
• 124-40-3 dimethyl amine 
• 158837-61-7 O-<(1S,2S)-N-Methylephedrine>-N,N'-diisopropylisourea 

Relevant articles and documents

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

Ephedrine- and pseudoephedrine-derived thioureas in asymmetric michael additions of keto esters and diketones to nitroalkenes

Ephedrine-derived bifunctional thioureas have been synthesized and applied as organocatalysts in Michael additions of 1,3-dicarbonyl compounds to nitroalkenes. Georg Thieme Verlag Stuttgart.

Dynamic resolution of α-bromo-α-alkyl esters using N-methyl pseudoephedrine as a chiral auxiliary: Asymmetric syntheses of α-amino acid derivatives

N-Methyl pseudoephedrine mediated dynamic resolution of α-bromo-α-alkyl esters in nucleophilic substitution reaction has been investigated. Best results are obtained when α-bromo-α-alkyl esters 1, 4 and 5 are allowed to equilibrate before the addition of nucleophile. This simple epimerization-substitution sequence provides a practical protocol for asymmetric syntheses of α-amino acid derivatives 2, 7 and 8 up to 98:2 enantiomeric ratio.