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
• Mol file: 90-81-3.mol

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*)-(+/-)-

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

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

(1R,2R)-pseudoephedrine

pseudoephedrine

Refernces

• 1、 Schulze, Matthias. "Synthesis of 2-Arylethylamines by the Curtius Rearrangement". experimental part. p. 1461 - 1476. Retrieved 2010/07/08.
• 2、 Bach,Schroder. "Photocycloaddition of N-acyl enamines to aldehydes and its application to the synthesis of diastereomerically pure 1,2-amino alcohols". . p. 1265 - 1273. Retrieved 2007/10/03.