46084-23-5

Basic information

• Product Name: (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol
• Synonyms: (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol
• CAS NO: 46084-23-5
• Molecular Weight: 167.208
• Mol File: 46084-23-5.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol(46084-23-5)
• EPA Substance Registry System: (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol(46084-23-5)

Safety Data

• Hazardous Substances Data: 46084-23-5(Hazardous Substances Data)

Usage

Description

(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol, also known as (R)-(-)-Ephedrine, is a chiral chemical compound with the molecular formula C10H15NO2. It is the naturally occurring enantiomer of the compound and is known for its stimulant, appetite suppressant, decongestant, and bronchodilator properties. Ephedrine works by directly stimulating the alpha and beta adrenergic receptors, which leads to increased heart rate, increased blood pressure, and bronchodilation.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a stimulant for its ability to increase heart rate and blood pressure, making it useful in treating conditions that require stimulation of the central nervous system.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as an appetite suppressant due to its ability to reduce appetite, which can be beneficial for weight management and obesity treatment.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a decongestant for its ability to relieve nasal congestion by constricting blood vessels in the nasal passages.
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a bronchodilator for its ability to widen the airways, which can be helpful in treating conditions like asthma and other respiratory disorders.
Used in Synthesis of Pharmaceuticals:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is used as a precursor in the synthesis of various pharmaceuticals, taking advantage of its chemical properties to create a range of different medications.
Used in Illicit Drug Manufacturing:
(R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol has also been used as a precursor for the illicit manufacturing of drugs, although this use is illegal and highly regulated due to the potential for abuse and adverse effects.
Regulation and Prescription Requirement:
Due to its potential for abuse and adverse effects, (R)-(-)-2-Amino-1-(4-methoxyphenyl)-1-ethanol is regulated in many countries and requires a prescription for medical use. This ensures that the compound is used responsibly and under the supervision of a healthcare professional.

Upstream product

• 637-69-4 4-Methoxystyrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 13603-63-9 (R)-1-(4-methoxyphenyl)ethane-1,2-diol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 67867-35-0 (E)-2-(4-methoxyphenyl)-2-oxoacetaldehyde oxime 
• 1287753-52-9 (E)-2-(4-methoxyphenyl)-2-oxoacetaldehyde O-benzyl oxime 
• 3883-94-1 2-amino-4'-methoxyacetophenone hydrochloride 
• 3755-89-3 N-(2-(4-methoxyphenyl)-2-oxoethyl)acetamide 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 675579-60-9 (2R,6S)-2-[(R)-1-(4-Methoxy-phenyl)-2-nitro-ethoxy]-6-methyl-tetrahydro-pyran 
• 604808-45-9 (S)-2-(diethylphosphoryloxy)-2-(4-methoxyphenyl)acetonitrile 
• 675579-61-0 (R)-1-(4-methoxyphenyl)-2-nitroethanol 
• 341513-45-9 (R)-β-azido-α-(4-methoxyphenyl)ethanol 

Downstream Products

• 1033599-29-9 C₂₇H₂₉NO₆ 
• 1033599-12-0 C₂₇H₂₉NO₆ 
• 37791-56-3 (R)-(-)-N-(2-hydroxy-2-(4-methoxyphenyl)ethyl)benzamide 

Relevant articles and documents

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells

The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalize

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.