90-83-5

Usage

Uses

Used in Respiratory Medications:
Racephedrine is used as a bronchodilator and decongestant for the treatment of symptoms related to respiratory conditions such as asthma and bronchitis. Its application is based on its mechanism of action, which involves stimulating the adrenergic receptors in the bronchial smooth muscles, leading to the relaxation and dilation of the airways.
Used in Over-the-Counter Medications:
Racephedrine is commonly found in over-the-counter medications due to its effectiveness in alleviating respiratory symptoms. However, its use is restricted in some countries due to its potential for abuse and side effects, such as increased heart rate and blood pressure.

Upstream product

• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 74-89-5 methylamine 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 90-82-4 pseudoephedrine 
• 90-81-3 ephedrine 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 79219-15-1 (S)-2-<(ethoxycarbonyl)amino>-1-phenyl-1-propanone 
• 72519-00-7 N-(α-phenylethylamino)ephedrine 
• 72519-00-7 (1R,2S,3S,5R)-N-(α-phenylethylamino)ephedrine 
• 77387-33-8 (1R,2S)-(-)-N-formylnorephedrine 
• 917-64-6 methyl magnesium iodide 
• 120443-82-5 (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 

Downstream Products

• 68578-91-6 2,2'-bis-[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-1,1'-benzo[1,2-d;4,5-d']bisoxazole-2,6-diyl-bis-ethanone 
• 117834-26-1 2,4-Di-tert-butyl-6-{[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phenol 
• 104807-68-3 (1R,2S)-2-[(2-Dimethylamino-ethyl)-methyl-amino]-1-phenyl-propan-1-ol 
• 116851-11-7 (1S,2R)-2-[Methyl-((S)-1-methyl-pyrrolidin-2-ylmethyl)-amino]-1-phenyl-propan-1-ol 
• 82485-40-3 ephedrine cyanamide 
• 132141-32-3 C₁₄H₂₀⁽²⁾HNO 
• 133157-43-4 C₁₉H₂₇N₂O₃ 
• 38925-77-8 4-methyl-N-(2-phenylethyl)benzamide 

Relevant academic research and scientific papers

Process for preparing beta-aminoalcohol from terminal olefin

The invention provides a method for preparing beta-aminoalcohol from terminal olefin. The method comprises the following steps: with the terminal olefin as a raw material, adding dibromohydantoin, conducting stirring, and then adding organic amine to obtain corresponding beta-aminoalcohol. The method has the advantages of mild conditions, easy operation, cheap raw materials, and wide application prospect.

BIOCATALYTICAL PROCESS FOR RACEMIZATION OF D-EPHEDRINE

This invention relates to methods for racemization of dextro-rotatory ephedrine via enzymatic kinetic conversion, and is particularly useful for conversion of dextro- rotatory ephedrine (d- ephedrine) to racemic mixture of dextro-rotatory ephedrine (d-ephedrine) and levo-rotatory ephedrine (l-ephedrine) to recover the levo-rotatory ephedrine that exhibit potential bronchodilatory and anti-hypotensive activities. The process provides a suspension of Rhizopus Oryzae fungi pellets in diammonium phosphate buffer having pH in the range of pH 5 to 9 and effective sonication to extract specific enzymes for inversion of functional groups present on the chiral carbon atom of d-ephedrine molecule at low temperature which has advantages of working at lower temperature range (20 to 50 °C), lower energy consumption, lesser formation of by-products.

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines

Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2

In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of C?H groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.

Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs

We report the use of a chiral Cu(II) 3D metal-organic framework (MOF) based on the tripeptide Gly-l-His-Gly (GHG) for the enantioselective separation of metamphetamine and ephedrine. Monte Carlo simulations suggest that chiral recognition is linked to preferential binding of one of the enantiomers as a result of either stronger or additional H-bonds with the framework that lead to energetically more stable diastereomeric adducts. Solid-phase extraction of a racemic mixture by using Cu(GHG) as the extractive phase permits isolating >50% of the (+)-ephedrine enantiomer as target compound in only 4 min. To our knowledge, this represents the first example of a MOF capable of separating chiral polar drugs.

Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids

An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from N-3-(p-tolyl) butanamides gave the respective enantiomerically pure acids.

POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE

Disclosed herein are polymorphic and amorphous forms of anhydrate, hydrate, and solvates of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide and methods of using such compositions for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging. Further disclosed are methods of making such polymorphic and amorphous forms.

A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide

An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions.