Ephedrine

Base Information

• Chemical Name: Ephedrine
• CAS No.: 299-42-3
• Deprecated CAS: 321-96-0,6912-63-6,6912-63-6
• Molecular Formula: C10H15NO
• Molecular Weight: 174.243
• Hs Code.: 29394100
• European Community (EC) Number: 206-080-5
• UNII: GN83C131XS
• DSSTox Substance ID: DTXSID0022985
• Nikkaji Number: J9.314I
• Wikipedia: Ephedrine
• Wikidata: Q219626
• NCI Thesaurus Code: C472
• RXCUI: 3966
• Pharos Ligand ID: 1HFH7FWPVHDF
• Metabolomics Workbench ID: 43520
• ChEMBL ID: CHEMBL211456
• Mol file: 299-42-3.mol

Synonyms:Ephedrine;Ephedrine Erythro Isomer;Ephedrine Hydrochloride;Ephedrine Renaudin;Ephedrine Sulfate;Erythro Isomer of Ephedrine;Hydrochloride, Ephedrine;Renaudin, Ephedrine;Sal Phedrine;Sal-Phedrine;SalPhedrine;Sulfate, Ephedrine

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Ephedrine

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 0.00865mmHg at 25°C
• Melting Point: 37-39 °C(lit.)
• Refractive Index: 1.528
• Boiling Point: 255 °C at 760 mmHg
• PKA: pKa 8.02 (Uncertain);9.5 (Uncertain)
• Flash Point: 85.6 °C
• PSA: 32.26000
• Density: 1.015 g/cm³
• LogP: 1.71880
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: 47.62g/L(25 oC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 165.115364102
• Heavy Atom Count: 12
• Complexity: 121

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)NC
• Isomeric SMILES: C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
• Recent ClinicalTrials: Evaluation of the Early Use of Norepinephrine in Major Abdominal Surgery on Postoperative Organ Dysfunction
• Recent EU Clinical Trials: Influence of vasopressors on brain oxygenation and microcirculation in anesthetized patients with cerebral tumors
• Recent NIPH Clinical Trials: Open lavel single center randomized parallel group trial concerning circulatory dynamics evaluation using PVI (Pleth Variability Index) between preoperative oral rehydration therapy group and prohibited preoperative eating and drinking group targeted at ASA 1or 2 of scheduled cesarean section for previous cesarean section, previous obstetric surgery or plevis position.
• Uses: Ephedrine, 1-phenyl-2-methylaminopropanol, C6H5 CH(OH)CH(NHCH3)CH3, is a white-to-colorless granular substance, unctuous (greasy) to the touch, and hygroscopic. The compound gradually decomposes upon exposure to light. Soluble in water, alcohol, ether, chloroform, and oils, and decomposes above this temperature. Ephedrine is isolated from stems or leaves of Ephedra, especially Ma huang (found in China and India). Medically, it is usually offered as the hydrochloride. In the treatment of bronchial asthma, ephedrine is known as a beta agonist. Compounds of this type reduce obstruction by activating the enzyme adenylate cyclase. This increases intracellular concentrations of cAMP (cyclic 3 5 -adenosine monophosphate) in bronchial smooth muscle and mast cells. Ephedrine is most useful for the treatment of mild asthma. In severe asthma, ephedrine rarely maintains completely normal airway dynamics over long periods. Ephedrine also has been used in the treatment of cerebral transient ischemic attacks, particularly with patients with vertabrobasilar artery insufficiency who have symptoms associated with relatively low blood pressure, or with postural changes in blood pressure. Ephedrine sulfate also has been used in drug therapy in connection with urticaria (hives). Medicine (bronchodilator).
• Therapeutic Function: Sympathomimetic; Bronchodilator
• Biological Functions: Ephedrine is a naturally occurring alkaloid that can cross the blood-brain barrier and thus exert a strong CNS-stimulating effect in addition to its peripheral actions.The latter effects are primarily due to its indirect actions and depend largely on the release of norepinephrine. However, ephedrine may cause some direct receptor stimulation, particularly in its bronchodilating effects. Because it resists metabolism by both COMT and MAO, its duration of action is longer than that of norepinephrine. As is the case with all indirectly acting adrenomimetic amines, ephedrine is much less potent than norepinephrine; in addition, tachyphylaxis develops to its peripheral actions. Unlike epinephrine or norepinephrine, however, ephedrine is effective when administered orally.
• Clinical Use: Ephedrine is useful in relieving bronchoconstriction and mucosal congestion associated with bronchial asthma, asthmatic bronchitis, chronic bronchitis, and bronchial spasms. It is often used prophylactically to prevent asthmatic attacks and is used as a nasal decongestant, as a mydriatic, and in certain allergic disorders. Although its bronchodilator action is weaker than that of isoproterenol, its oral effectiveness and prolonged duration of action make it valuable in the treatment of these conditions. Because of their oral effectiveness and greater bronchiolar selectivity, terbutaline and albuterol are replacing ephedrine for bronchodilation.

Technology Process of Ephedrine

There total 133 articles about Ephedrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(+/-)-erythro-methylephedrine (552-79-4,1201-56-5,14222-20-9,17605-71-9,39263-91-7,42151-56-4,51018-28-1,62560-55-8,87040-40-2) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + ephedrine (90-81-3,90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,7009-81-6,90-83-5,6912-63-6) + benzaldehyde (100-52-7) + acetaldehyde (75-07-0,9002-91-9) + dimethyl amine (124-40-3)

Guidance literature:

With water; at 25 ℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;

Reference yield: 86.0%

(2RS,3RS)-N-(2-phenyloxetan-3-yl)formamide → rac-pseudoephedrine (90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,90-81-3,7009-81-6,90-83-5,6912-63-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(97)00721-1

Reference yield: 79.0%

(+/-)-erythro-methoxyephedrine (2226-33-7,46288-71-5,79297-94-2,79297-97-5,82950-54-7,133161-06-5) → methanol (67-56-1) + ephedrine (90-81-3,90-82-4,299-42-3,321-97-1,321-98-2,4125-58-0,34783-90-9,38732-95-5,53214-57-6,7009-81-6,90-83-5,6912-63-6) + benzaldehyde (100-52-7) + acetaldehyde (75-07-0,9002-91-9) + dimethyl amine (124-40-3) + methylamine (74-89-5)

Guidance literature:

With water; at 25 ℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;

upstream raw materials:

methcathinone

(RS)-1-hydroxy-1-phenylpropan-2-one

methylamine

2-bromo-1-phenyl-1-propanone

Downstream raw materials:

phendimetrazine

(+/-)-3,4r-dimethyl-5t-phenyl-2ξ-[2]pyridyl-oxazolidine

((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-((Ξ)-β-hydroxy-phenethyl)-methyl-amine

(1R,2S)-2-(butyl(methyl)amino)-1-phenylpropan-1-ol

Refernces

• 1、 Navarro-Sánchez, José,Argente-García, Ana I.,Moliner-Martínez, Yolanda,Roca-Sanjuán, Daniel,Antypov, Dmytro,Campíns-Falcó, Pilar,Rosseinsky, Matthew J.,Martí-Gastaldo, Carlos. "Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs". . p. 4294 - 4297. Retrieved 2017.
• 2、 -. "Process for preparing beta-aminoalcohol from terminal olefin". Paragraph 0031; 0032; 0048. . Retrieved 2020/06/17.
• 3、 Alcalde, Miguel,Arends, Isabel W. C. E.,Hollmann, Frank,Paul, Caroline E.,Rauch, Marine C. R.,Tieves, Florian. "Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media". . . Retrieved 2019/08/30.