2272-83-5

Basic information

• Product Name: (1S,2R)-(+)-N-Acetyl Ephedrine
• Synonyms: (1S,2R)-(+)-N-Acetyl Ephedrine;[R-(R*,S*)]-N-(2-Hydroxy-1-Methyl-2-phenylethyl)-N-MethylacetaMide;L-erythro-N-(β-Hydroxy-α-Methylphenethyl)-N-MethylacetaMide;N-[(1S,2R)-2-Hydroxy-1-Methyl-2-phenylethyl]-N-MethylacetaMide;N-Acetylephedrine
• CAS NO: 2272-83-5
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.26888
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2272-83-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 103.5-104 °C
• Boiling Point: 361.2°C at 760 mmHg
• Flash Point: 172.3°C
• Appearance: /
• Density: 1.083g/cm³
• Vapor Pressure: 7.53E-06mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• PKA: 13.52±0.20(Predicted)
• CAS DataBase Reference: (1S,2R)-(+)-N-Acetyl Ephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-(+)-N-Acetyl Ephedrine(2272-83-5)
• EPA Substance Registry System: (1S,2R)-(+)-N-Acetyl Ephedrine(2272-83-5)

Safety Data

• Hazardous Substances Data: 2272-83-5(Hazardous Substances Data)

Usage

Description

(1S,2R)-(+)-N-Acetyl Ephedrine is an acetylated derivative of the αand β-adrenergic agonist Ephedrine, possessing a similar response to the parent drug in terms of the immediate onset and short duration of its effects.

Uses

Used in Pharmaceutical Industry:
(1S,2R)-(+)-N-Acetyl Ephedrine is used as a pharmaceutical agent for its adrenergic agonist properties, which can provide immediate and short-term effects on the body's physiological processes.
Used in Research Applications:
(1S,2R)-(+)-N-Acetyl Ephedrine is used as a research compound to study the effects of adrenergic agonists on various biological systems and to develop new therapeutic agents based on its structure and activity.

InChI:InChI=1/C12H17NO2/c1-9(13(3)10(2)14)12(15)11-7-5-4-6-8-11/h4-9,12,15H,1-3H3/t9-,12-/m0/s1

Upstream product

• 67-56-1 methanol 
• 110-96-3 diisobutylamine 
• 14383-62-1 acetic acid-((1R,2S)-2-methylamino-1-phenyl-propylester); hydrochloride 
• 67-66-3 chloroform 
• 299-42-3 ephedrine 
• 108-24-7 acetic anhydride 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 90-82-4 rac-pseudoephedrine 
• 29724-89-8 N-((1RS,2RS)-2-chloro-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide 
• 90-81-3 ephedrine 
• 1630-34-8 (1RS:2SR)-2-methylamino-1-acetoxy-1-phenyl-propane; hydrochloride 

Downstream Products

• 48141-64-6 (1R,2S)-1-phenyl-2-(ethylmethylamino)propanol 
• 299-42-3 ephedrine 
• 90-82-4 pseudoephedrine 
• 145388-32-5 (2S)-1<2-(2-Dimethylaminoethyl)phenyl>-N-ethyl-N-methyl-2-propanamin 
• 145388-31-4 (2S)-2<2(Ethyl-methyl-amino)propyl>-N,N-dimethylphenylacetamid 
• 89617-55-0 (S)-(+)-N-Acetyl-N-methylamphetamine 
• 1351949-89-7 C₁₉H₂₈N₄O₂ 
• 1351949-56-8 C₁₅H₁₉NO₂ 

Relevant articles and documents

Comparison of diffusion coefficients for matched pairs of macrocyclic and linear molecules over a drug-like molecular weight range

The diffusion coefficients of a series of closely matched pairs of macrocyclic and linear molecules have been compared using NMR spectroscopy. The macrocyclic series was designed both to overlap with and extend beyond the molecular weight range typically employed for drug-like molecules. The linear molecules each represent a carbogenic fission of their macrocyclic counterparts, designed to minimize differences in functionality and physicochemical properties. Each series of molecules was prepared using copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions conducted in a flow using a copper tube. The macrocyclic series exhibited consistently higher diffusion across the entire molecular weight range studied. The fold difference in diffusion coefficients between the macrocyclic and linear analogues appeared to be independent of either solvent viscosity or dielectric environment.

Reactions of (-)-Ephedrine, (+)-Norpseudoephedrine and Derivatives with N,N-Dimethylacetamid-dimethylacetal and N,N-Dimethylformamid-dimethylacetal

The reactivity of (-)-ephedrine (2) and (+)-norpseudoephedrine (3) towards the amid-acetals 1 a/b has been studied.Both 2 and 3 were acetylated resp. formylated at first at the amino group.Nevertheless, derivatives of 2 and 3 possessing a trisubstituted amino group react with 1 a in a sigmatropic rearrangement to ortho substituted dimethylcarbamoylmethyl derivatives.By subsequent reduction with lithiumaluminiumhydride the aromatic compounds 8, 13, and 18 with two aminoethyl groups are easily available.In contrast to these results 1 b did not furnish any rearrangement products. Keywords. (-)-Ephedrine; (+)-Norpseudoephedrine; N,N-Dimethylacetamid-dimethylacetal; N,N-Dimethylformamid-dimethylacetal; Sympathomimetic effects; Sigmatropic rearrangements.