51018-28-1

Basic information

• Product Name: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE
• Synonyms: (+)-1S,2S-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYLEPHEDRINE;(+)-1S,2S-N-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYL-PSI-EPHEDRINE;METHYLPSEUDOEPHEDRINE;METHYLPSEUDOEPHEDRINE, (+)-1S,2S-;METHYLPSEUDOEPHEDRINE, (+)-1S,2S-N-
• CAS NO: 51018-28-1
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• EINECS: 209-022-7
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 51018-28-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 29-31 °C(lit.)
• Boiling Point: 145 °C24 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0020 (rough estimate)
• Vapor Pressure: 0.0108mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.88±0.20(Predicted)
• CAS DataBase Reference: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(51018-28-1)
• EPA Substance Registry System: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(51018-28-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 51018-28-1(Hazardous Substances Data)

Usage

Description

(1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE, also known as N-Methylpseudoephedrine, is a N-methylated analogue of the non-selective adrenergic agonist Pseudoephedrine. It is an alkaloid derived from Ephedra species, which are widely used in Chinese medicine. (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE is characterized by its white solid appearance and possesses unique chemical properties that make it valuable in various applications.

Uses

Used in Pharmaceutical Industry:
(1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE is used as an active pharmaceutical ingredient for its adrenergic agonist properties. It is particularly valuable due to its N-methylation, which may enhance its effectiveness in treating certain conditions related to the adrenergic system.
Used in Chinese Medicine:
In the field of Chinese medicine, (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE is used as a key component in various traditional remedies. Its presence in Ephedra species contributes to the therapeutic effects of these plants, which have been utilized for centuries in Chinese medicinal practices.
Used in Chemical Research:
As a unique alkaloid with specific stereochemistry, (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE is also used in chemical research for studying the structure-activity relationships of adrenergic agonists and for developing new drugs with improved pharmacological properties.
Used in Synthesis of Other Compounds:
Due to its chemical structure, (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE can be used as a starting material or intermediate in the synthesis of other related compounds with potential applications in medicine, pharmaceuticals, or other industries.

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+/m0/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 
• 299-42-3 (R,R)-(-)-pseudoephedrine 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 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 
• 942-45-0 (1S,2S)-β-chloro-N,N',α-trimethylbenzeneethanammonium chloride 
• 445298-95-3 (S,S)-N-methylpseudoephedrine α-bromo-α-methylacetate 

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.

1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89 percent. The stereoelectronic effects operating in the reactions are discussed.

Facile inversion of configuration of N-Boc-β-aminoalcohols via S(N)2 cyclization to oxazolidinones

Oxazolidinones are obtained by the cyclization of mesylates derived from N-Boc-β-Aminoalcohols. Hydrolysis of the N-Boc-Oxazolidinones regenerates the protected aminoalcohols with inverted configuration at the hydroxy group. (C) 2000 Elsevier Science Ltd.