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:

ephedrine

L-erythro-2-amino-1-(4-nitro-phenyl)-propanol-⁽¹⁾

NH-benzyl-(1R,2S)-norephedrine

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

Refernces

Discovery of a PCAF Bromodomain Chemical Probe

10.1002/anie.201610816

The study reports the discovery of L-45, also known as L-Moses, which is the first potent, selective, and cell-active chemical probe for the PCAF bromodomain (Brd). The research involved iterative cycles of rational inhibitor design, biophysical characterization, and synthesis to develop L-45 from readily available (1R,2S)-(+)-norephedrine in enantiopure form. The chemical probe serves to disrupt the PCAF-Brd interaction with histone H3.3 in cells, as demonstrated using a nanoBRET assay. The study also presents a co-crystal structure of L-45 with the homologous Brd PfGCN5 from Plasmodium falciparum, which rationalizes the high selectivity for PCAF and GCN5 bromodomains. The chemicals used in the study include triazolopthalazine-based compounds, various amine nucleophiles, and other synthetic intermediates, all of which were employed in the development and testing of L-45 for its potential as a therapeutic target in diseases such as cancer, HIV infection, and neuroinflammation. The purpose of these chemicals was to create a compound that could selectively target and modulate the PCAF Brd, providing a tool for investigating the role of PCAF in disease states and potentially leading to new treatments.

Enantiopure β³-neopentylglycine: synthesis and resolution

10.1016/j.tetasy.2009.01.018

The research aims to develop a large-scale synthesis procedure for enantiopure b3-neopentylglycine and its Cbz-protected derivative. L-(-)-norephedrine is used as a resolving agent to separate the enantiomers of Cbz-b3-neopentylglycine. The study found that L-(-)-norephedrine, compared to other chiral amines tested, provided the best results in terms of yield and enantiopurity. Specifically, it formed diastereomerically pure salts with the Cbz-protected b3-neopentylglycine, allowing for the efficient resolution of the racemic mixture. The use of L-(-)-norephedrine resulted in a diastereomeric ratio of approximately 2.5:97.5 (R:S) and an S-factor of around 0.70–0.74, indicating high enantioselectivity. The study concludes that this resolution method is efficient and represents a unique example of resolving an aliphatic b-amino acid, providing a valuable route for synthesizing enantiomerically pure b3-neopentylglycine for potential applications in pharmaceuticals.