299-42-3

Basic information

• Product Name: Ephedrine
• Synonyms: [r-(r*,s*)]-alpha-[1-(methylamino)ethyl]-benzenemethanol;1-ALPHA-(1-METHYLAMINOETHYL)BENZYL ALCOHOL;(1R,2S)-2-METHYLAMINO-1-PHENYL-1-PROPANOL;(1R,2S)-(-)-ALPHA-(1-METHYLAMINOETHYL)BENZYL ALCOHOL;(1R,2S)-(-)-EPHEDRINE;(1R,1S)-(-)-2-(METHYLAMINO)-1-PHENYLPROPAN-1-OL;(1R,1S)-(-)-EPHEDRINE;(-)-EPHEDRIN
• CAS NO: 299-42-3
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 206-080-5
• Product Categories: Miscellaneous Natural Products;chiral;pharmaceutical intermediate
• Mol File: 299-42-3.mol

Chemical Properties

• Melting Point: 37-39 °C(lit.)
• Boiling Point: 255 °C(lit.)
• Flash Point: 186 °F
• Appearance: white crystals or powder
• Density: 1.124 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00865mmHg at 25°C
• Refractive Index: 1.4820 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• PKA: pKa 8.02 (Uncertain);9.5 (Uncertain)
• Water Solubility: 47.62g/L(25 oC)
• Stability: Stable. Combustible. Incompatible with strong acids, acid chlorides, acid anhydrides, strong oxidizing agents. May discolour in
• Merck: 13,3639
• BRN: 2208730
• CAS DataBase Reference: Ephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: Ephedrine(299-42-3)
• EPA Substance Registry System: Ephedrine(299-42-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-25
• WGK Germany: 1
• RTECS: KB0700000
• F: 3-10
• Hazardous Substances Data: 299-42-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

Upstream product

• 5650-44-2 methcathinone 
• 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 
• 50-00-0 formaldehyd 
• 492-41-1 (1R,2S)-norephedrine 
• 90-82-4 pseudoephedrine 
• 5650-44-2 (-)-Methcathinone 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 593-51-1 methylamine hydrochloride 
• 90-81-3 ephedrine 
• 16735-30-1 (S)-2-(benzyl-methyl-amino)-1-phenyl-propan-1-one 
• 127-09-3 sodium acetate 

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 
• 74100-88-2 2-[(2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-1-naphtho[1,2-d]oxazol-2-yl-ethanone 
• 62878-42-6 5-[N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-glycyl]-2-phenyl-5H-oxazolo[4,5-b]phenoxazine 
• 17605-71-9 2-dimethylamino-1-phenyl-propan-1-ol 
• 62878-43-7 5-[N-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-glycyl]-2-(4-methoxy-phenyl)-5H-oxazolo[4,5-b]phenoxazine 
• 53214-55-4 C₁₅H₂₇N₂O₄P 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 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 
• 86682-51-1 3',4',5',6'-Tetrahydro-4',5'-dimethyl-6'-phenylspiro<1,3,4>oxaziridin> 
• 67055-59-8 Cefedrin 
• 124497-76-3 4,5-Dimethyl-2,6-diphenyl-morpholin-2-ol; hydrochloride 
• 92490-07-8 CH₃NHCH(CH₃)CH(Ph)OPPh₂ 
• 116851-11-7 (1S,2R)-2-[Methyl-((S)-1-methyl-pyrrolidin-2-ylmethyl)-amino]-1-phenyl-propan-1-ol 

Relevant articles and documents

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.

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.

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.

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.

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.

PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV

A process for preparing [(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or (1R,2S)-(-)- ephedrine, thus preparing the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis- (1R,2S)-(-)-ephedrine salt of [(1S,2S)-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or (1R,2S)-(-)-ephedrine from the precipitated salt obtained in step (b).

Synthesis of 2-Arylethylamines by the Curtius Rearrangement

2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield. Copyright Taylor & Francis Group, LLC.

Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf

Ephedra sinica Stapf (Ephedraceae) is a widely used Chinese medicinal plant (Chinese name: Ma Huang). The main active constituents of E. sinica are the unique and taxonomically restricted adrenergic agonists phenylpropylamino alkaloids, also known as ephedrine alkaloids: (1R,2S)-norephedrine (1S,2S)-norpseudoephedrine, (1R,2S)-ephedrine, (1S,2S)-pseudoephedrine, (1R,2S)-N-methylephedrine and (1S,2S)-N-methylpseudoephedrine. GC-MS analysis of freshly picked young E. sinica stems enabled the detection of 1-phenylpropane-1,2-dione and (S)-cathinone, the first two putative committed biosynthetic precursors to the ephedrine alkaloids. These metabolites are only present in young E. sinica stems and not in mature stems or roots. The related Ephedra foemina and Ephedra foliata also lack ephedrine alkaloids and their metabolic precursors in their aerial parts. A marked diversity in the ephedrine alkaloids content and stereochemical composition in 16 different E. sinica accessions growing under the same environmental conditions was revealed, indicating genetic control of these traits. The accessions can be classified into two groups according to the stereochemistry of the products accumulated: a group that displayed only 1R stereoisomers, and a group that displayed both 1S and 1R stereoisomers. (S)-cathinone reductase activities were detected in E. sinica stems capable of reducing (S)-cathinone to (1R,2S)-norephedrine and (1S,2S)-norpseudoephedrine in the presence of NADH. The proportion of the diastereoisomers formed varied according to the accession tested. A (1R,2S)-norephedrine N-methyltransferase capable of converting (1R,2S)-norephedrine to (1R,2S)-ephedrine in the presence of S-adenosylmethionine (SAM) was also detected in E. sinica stems. Our studies further support the notion that 1-phenylpropane-1,2-dione and (S)-cathinone are biosynthetic precursors of the ephedrine alkaloids in E. sinica stems and that the activity of (S)-cathinone reductases directs and determines the stereochemical branching of the pathway. Further methylations are likely due to N-methyltransferase activities.

The preparation of stable aziridinium ions and their ring-openings

The reaction of enantiomerically pure 2-substituted 1-phenylethyl-aziridine with methyl trifluoromethanesulfonate generated a stable methylaziridinium ion, which was reacted with various external nucleophiles, including nitrile, to yield synthetically valuable and optically pure acyclic amine derivatives in a completely regio- and stereoselective manner. The Royal Society of Chemistry.