d-Ephedrine

Base Information

• Chemical Name: d-Ephedrine
• CAS No.: 90-81-3
• Deprecated CAS: 38732-95-5,90-83-5,4607-45-8
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• European Community (EC) Number: 206-293-3,202-017-0
• UNII: 03VRY66076,72087NSY56
• DSSTox Substance ID: DTXSID20891194,DTXSID60889333
• Nikkaji Number: J59.191B
• Wikidata: Q22330463
• NCI Thesaurus Code: C81363
• ChEMBL ID: CHEMBL2110656

Synonyms:d-Ephedrine;(+)-Ephedrine;L-(+)-Ephedrine;racephedrine;(+)-Ephedrin;321-98-2;90-81-3;(+)-Ephedrine anhydrous;EPHEDRINE, (+)-;(1S,2R)-Ephedrine;D-(-)-Ephedrine;Ephedrine, D-(-)-;2-Methylamino-1-phenylpropan-1-ol;EINECS 206-293-3;(1S,2R)-2-(methylamino)-1-phenylpropan-1-ol;BRN 4231286;NIOSH/KB0650000;UNII-03VRY66076;UNII-72087NSY56;(+-)-Ephedrine;03VRY66076;72087NSY56;( inverted exclamation markA)-Ephedrine;Benzenemethanol, alpha-((1R)-1-(methylamino)ethyl)-, (alphaS)-;Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (S-(R*,S*))-;Racephedrine [INN:BAN];KB06500000;4-13-00-01881 (Beilstein Handbook Reference);(+)-(1s,2r)-ephedrine;alpha-(1-(Methylaminoethyl)benzenemethanol, (S-(R*,S*)-;Ephedrine DL-form;EINECS 202-017-0;Benzenemethanol, .alpha.-[(1R)-1-(methylamino)ethyl]-, (.alpha.S)-;Benzenemethanol, .alpha.-[(1R)-1-(methylamino)ethyl]-, (.alpha.S)-rel-;BRN 3197916;(1R,2S)-(-)-ephedrine;EPHEDRINE, (+-)-;Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [S-(R*,S*)]-;BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,S*))-;.psi.-Ephedrine;.psi.-Ephedrin;BENZENEMETHANOL, .ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-REL-;D-.psi.-Ephedrine;(+/-)-ephedrine;Novafed (Salt/Mix);Sinufed (Salt/Mix);Tussaphed (Salt/Mix);(+)-erythro-ephedrine;Symptom 2 (Salt/Mix);L(+)-.psi.-Ephedrine;RACEPHEDRINE [INN];.psi.-Ephedrine, (+)-;(R*,S*)-(+-)-alpha-(1-(Methylamino)ethyl)benzyl alcohol;(R*,S*)-(+-)-alpha-[1-(methylamino)ethyl]benzyl alcohol;(R*,S*)-(.+-)-alpha-[1-(methylamino)ethyl]benzylalkohol;(1s,2r)-(-)-ephedrine;RACEPHEDRINE [WHO-DD];SCHEMBL420779;Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [S-(R*,R*)]-;Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R*,S*)-(+-)-;EPHEDRINE DL-FORM [MI];Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, (R*,S*)-(.+-.)-;Benzenemethanol, alpha-((1R)-1-(methylamino)ethyl)-, (alphaS)-rel-;CHEMBL2110656;HY-B0980A;DTXSID20891194;DTXSID60889333;PDSP1_001345;PDSP2_001329;PDSP2_001331;AKOS027326694;CS-4471;LS-63961;2-(Methylamino)-1-phenyl-1-propanol, d-.psi.- #;Q22330463;[S-(R*,R*)]-.alpha.-[1-(methylamino)ethyl]benzenemethanol;Benzenemethanol, a-[(1R)-1-(methylamino)ethyl]-, (aS)-rel-;.alpha.-((1S)-1-(Methylamino)ethyl)benzyl alcohol, (.alpha.S)-;.alpha.-[(1S)-1-(Methylamino)ethyl]benzenemethanol, (.alpha.S)-;BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R*,S*)-(+/-)-

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Chemical Property of d-Ephedrine

Chemical Property:

• Melting Point: 75°
• Refractive Index: 1.4820 (estimate)
• Boiling Point: 255 °C at 760 mmHg
• PKA: 13.96±0.20(Predicted)
• Flash Point: 85.6 °C
• PSA: 32.26000
• Density: 1.015 g/cm³
• LogP: 1.71880
• 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: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)NC
• Isomeric SMILES: C[C@H]([C@H](C1=CC=CC=C1)O)NC
• Uses: Medicine (also as hydrochloride and sulfate).

Technology Process of d-Ephedrine

There total 113 articles about d-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:

ephedrine

sodium methylate

pseudoephedrine

(1R,2R)-pseudoephedrine

Downstream raw materials:

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

trans-3,4-dimethyl-5-phenyloxazolidin-2-one

(+/-)-N-methylpseudoephedrine

(+/-)-3,4r-dimethyl-5t-phenyl-oxazolidine

Refernces

Circular dichroism and circularly polarized luminescence triggered by self-assembly of tris(phenylisoxazolyl)benzenes possessing a perylenebisimide moiety

10.1039/c2cc31512b

The research focuses on the self-assembly of chiral tris(phenylisoxazolyl)benzenes containing a perylenebisimide (PBI) moiety, which form helical stacks exhibiting strong circular dichroism (CD) and circularly polarized luminescence (CPL) controlled by external stimuli such as solvent properties, temperature, and concentration. The experiments involved synthesizing the chiral compounds, followed by analyses using 1H NMR and UV–vis absorption spectroscopy to study their self-assembling behavior and the resulting optical properties. The 1H NMR spectra revealed concentration-dependent shifts indicating the formation of stacked assemblies, while UV–vis absorption demonstrated the influence of temperature and solvent on the absorption characteristics. The CD spectra showed a mirror image relationship between the chiral assemblies, and CPL measurements confirmed the emission properties of the assemblies in different solvents, highlighting the unique chiroptical properties induced by the self-assembly process.