L-(-)-Ephedrine

Base Information

• Chemical Name: L-(-)-Ephedrine
• CAS No.: 492-41-1
• Deprecated CAS: 134-60-1,36393-57-4,700-65-2
• Molecular Formula: C9H13NO
• Molecular Weight: 151.208
• Hs Code.: 2939440000
• European Community (EC) Number: 207-755-7,238-900-2,211-850-9
• NSC Number: 17704
• UNII: 33RU150WUN,57B9YG5Y1E
• DSSTox Substance ID: DTXSID10889348
• Nikkaji Number: J22.046I
• Wikipedia: Phenylpropanolamine
• Wikidata: Q26840801
• NCI Thesaurus Code: C29364
• Pharos Ligand ID: HKTM6W2NXZZH
• Metabolomics Workbench ID: 123369
• ChEMBL ID: CHEMBL136560
• Mol file: 492-41-1.mol

Synonyms:Benzenemethanol,a-(1-aminoethyl)-, [R-(R*,S*)]-;(-)-Norephedrin;(-)-Norephedrine;(-)-Phenylpropanolamine;(-)-erythro-2-Amino-2-methyl-1-phenylethanol;(1R,2S)-(-)-Norephedrine;(1R,2S)-2-Amino-1-phenyl-1-propanol;(1R,2S)-Norephedrine;(1S,2R)-2-Hydroxy-2-phenyl-1-methyl-1-aminoethane;(R,S)-(-)-Norephedrine;L-Norephedrine;NSC 17704;Norephedrine, (-)-;erythro-(1R,2S)-Norephedrine;

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Chemical Property of L-(-)-Ephedrine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.0011mmHg at 25°C
• Melting Point: 51-53 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 288.1 °C at 760 mmHg
• PKA: 9.958(at 10℃)
• Flash Point: 128.1 °C
• PSA: 46.25000
• Density: 1.071 g/cm³
• LogP: 1.76750
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 151.099714038
• Heavy Atom Count: 11
• Complexity: 110

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)N
• Isomeric SMILES: C[C@@H]([C@@H](C1=CC=CC=C1)O)N
• Description: This alkaloid was first isolated by Kanao from the Chinese drug 'Ma-Huang' (Ephedra sinica Stapf.) and later by Wolfes from E. helvetica C. A. Meyer and E. distachya Linn. It forms a crystalline mass and has [α] 20 D - 14.56° (EtOH). Several crystalline salts and derivatives are known: the hydrochloride has m.p. 171-2°C; [α] 20 D- 33.27° (H20); the sulphate dihydrate, m.p. 285-6°C (dry, dec.); [α] 28 D- 31.99° (H20); the aurichloride, m.p. 188°C; platinichloride, m.p. 221°C (dec.); (-)-hydrogen tartrate, m.p. about 160° after sintering at 130°C; oxalate, m.p. 245°C (dec.) and the p-nitrobenzoyl derivative, m.p. 175-6°C; [α] 28 D- 49.58° (CHCI3).The (+)-form has m.p. 52°C; [α] 27 D + 14.76° (EtOH), yielding a hydro_x0002_chloride, m.p. 171-2°C; [α] 27 D + 33.4° (EtOH); sulphate dihydrate, m.p. 285- 6°C (dry, dec.); [α] 27 D+ 31.51 0 C (H20); aurichloride, m.p. 188°C (dec.) and platinichloride, m.p. 221.5°C (dec.). The (±)-form crystallizes as colourless plates from Et20, m.p. 104-5°C and also furnishes a series of crystalline salts and derivatives.
• Uses: A metabolite of Phenmetrazine.

Technology Process of L-(-)-Ephedrine

There total 78 articles about L-(-)-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: 75.0%

(1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol (154170-05-5) → (1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; at 35 ℃; for 144h; under 2280.15 Torr; Product distribution / selectivity;

Reference yield: 72.0%

tert-butyl ((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)carbamate (113322-99-9) → (1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

Reference yield: 71.5%

(4S,5R)-4-methyl-5-phenyl-[1,2,3]oxathiazolidine 2,2-dioxide (1380313-45-0) → (1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h; optical yield given as %ee;

DOI:10.1021/jo300867y

upstream raw materials:

u-2-amino-1-phenylpropan-1-ol

(R)-1-hydroxy-1-phenyl-2-propanone

(R)-1-hydroxy-1-phenylpropan-2-one oxime

3-phenyl-propionaldehyde

Downstream raw materials:

4-nitro-benzoic acid-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethylamide); N-(4-nitro-benzoyl)-(-)-norephedrine

phenylacetic acid-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethylamide)

(1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol

(1R,2S)-(+)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol

Refernces

• 1、 Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.. "Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase". . p. 1067 - 1078. Retrieved 2018/08/01.
• 2、 -. "Method for preparing norephedrine and norpseudoephedrine". Paragraph 0004; 0012; 0013; 0014; 0015. . Retrieved 2017/04/29.