492-41-1

Basic information

• Product Name: L-(-)-Ephedrine
• Synonyms: L-(-)-NOREPHEDRINE;DL-NOREPHEDRINE;AURORA KA-7791;AURORA KA-7792;2-AMINO-1-PHENYL-1-PROPANOL;(1R,2S)-(-)-2-AMINO-1-PHENYL-1-PROPANOL;(1R,2S)-2-AMINO-1-PHENYL-1-PROPANOL;(1R,2S)-2-AMINO-1-PHENYLPROPAN-1-OL
• CAS NO: 492-41-1
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• EINECS: 207-755-7
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 492-41-1.mol
• Article Data: 37

Chemical Properties

• Melting Point: 51-53 °C(lit.)
• Boiling Point: 273.23°C (rough estimate)
• Flash Point: >230 °F
• Appearance: white powder
• Density: 1.0406 (rough estimate)
• Vapor Pressure: 0.0011mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: 2-8°C
• PKA: 9.958(at 10℃)
• Stability: Stable. Incompatible with strong oxidizing agents. May discolour on exposure to light.
• CAS DataBase Reference: L-(-)-Ephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: L-(-)-Ephedrine(492-41-1)
• EPA Substance Registry System: L-(-)-Ephedrine(492-41-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: RC2275000
• F: 3-8-10
• Hazardous Substances Data: 492-41-1(Hazardous Substances Data)

Usage

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.

Chemical Properties

white powder

Uses

A metabolite of Phenmetrazine.

Safety Profile

A human poison by ingestion. Poison experimentally by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by an unspecified route. Human systemic effects by ingestion: sleep, increased pulse rate without blood pressure decrease, and chronic pulmonary edema or congestion, convulsions, headache, and blood pressure elevation. Used in production of drugs of abuse. When heated to decomposition it emits toxic fumes of NOx.

References

Kanao., Ber., 63,95 (1930) Wolfes., Arch. Pharrn., 268,87 (1930) Hey., J. Chern. Soc., 1232 (1930) Akabori, Momotani., J. Chern. Soc., Japan, 64, 608 (1943) Hoover, Hass., J. Org. Chern., 12,506 (1947)

InChI:InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 93643-58-4 (4S,5R)-2,4-Dimethyl-2,5-diphenyl-oxazolidine 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 132273-10-0 benzostabase of Ala-OMe 
• 123367-08-8 (S)-1-Phenyl-2-pyrrol-1-yl-propan-1-ol 
• 630-19-3 pivalaldehyde 
• 123-72-8 butyraldehyde 
• 113322-99-9 tert-butyl ((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)carbamate 
• 79-24-3 Nitroethane 
• 100-52-7 benzaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 55253-39-9 (R)-1-hydroxy-1-phenylpropan-2-one oxime 
• 104-54-1 3-Phenylpropenol 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 

Downstream Products

• 299-42-3 ephedrine 
• 61347-76-0 NH-benzyl-(1R,2S)-norephedrine 
• 150125-70-5 (2S,4S,5R)-2-<(R)-α-<(tert-butyldimethylsilyl)oxy>benzyl>-2,4-dimethyl-5-phenyloxazolidine 
• 93643-59-5 (4S,5R)-2-tert-Butyl-2,4-dimethyl-5-phenyl-oxazolidine 
• 115651-77-9 (1R,2S)-(+)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol 
• 126517-20-2 D(+)-N-(2-Benzoyl-4-chlorophenyl)-2-(1-hydroxy-1-phenyl-2-propylamino)acetamide 
• 115296-92-9 6-N-tert.-Butyloxycarbonyl-6-amino-capronsaeure-(1'S,2'R)(1'-methyl-2'-hydroxy-2'-phenylethyl)-amid 
• 99285-26-4 N-(E-2,6-heptanedienoyl)-l-ephedrine 
• 144694-12-2 [4-((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethylamino)-5-nitro-pyridin-2-yl]-carbamic acid ethyl ester 
• 144694-27-9 [4-Amino-6-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethylamino)-5-nitro-pyrimidin-2-yl]-carbamic acid methyl ester 
• 144694-13-3 [6-Hydroxy-4-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethylamino)-5-nitro-pyridin-2-yl]-carbamic acid ethyl ester 
• 2153-98-2 (-)-Norpseudoephedrine hydrochloride 
• 1201-74-7 (R)-[1-(naphthalen-2-yl)ethyl]amine 
• 552-79-4 (-)-N-methylephedrine 

Relevant articles and documents

High Regio- and Stereoselective Multi-enzymatic Synthesis of All Phenylpropanolamine Stereoisomers from β-Methylstyrene

We present a one-pot cascade for the synthesis of phenylpropanolamines (PPAs) in high optical purities (er and dr up to >99.5 %) and analytical yields (up to 95 %) by using 1-phenylpropane-1,2-diols as key intermediates. This bioamination entails the combination of an alcohol dehydrogenase (ADH), an ω-transaminase (ωTA) and an alanine dehydrogenase to create a redox-neutral network, which harnesses the exquisite and complementary regio- and stereo-selectivities of the selected ADHs and ωTAs. The requisite 1-phenylpropane-1,2-diol intermediates were obtained from trans- or cis-β-methylstyrene by combining a styrene monooxygenase with epoxide hydrolases. Furthermore, in selected cases, the envisioned cascade enabled to obtain the structural isomer (1S,2R)-1-amino-1-phenylpropan-2-ol in high optical purity (er and dr >99.5 %). This is the first report on an enzymatic method that enables to obtain all of the four possible PPA stereoisomers in great enantio- and diastereo-selectivity.

Selective Nonsteroidal Glucocorticoid Receptor Modulators for the Inhaled Treatment of Pulmonary Diseases

A class of potent, nonsteroidal, selective indazole ether-based glucocorticoid receptor modulators (SGRMs) was developed for the inhaled treatment of respiratory diseases. Starting from an orally available compound with demonstrated anti-inflammatory activity in rat, a soft-drug strategy was implemented to ensure rapid elimination of drug candidates to minimize systemic GR activation. The first clinical candidate 1b (AZD5423) displayed a potent inhibition of lung edema in a rat model of allergic airway inflammation following dry powder inhalation combined with a moderate systemic GR-effect, assessed as thymic involution. Further optimization of inhaled drug properties provided a second, equally potent, candidate, 15m (AZD7594), that demonstrated an improved therapeutic ratio over the benchmark inhaled corticosteroid 3 (fluticasone propionate) and prolonged the inhibition of lung edema, indicating potential for once-daily treatment.

Method for preparing norephedrine and norpseudoephedrine

The invention relates to a method for preparing (1R, 2S)-norephedrine, (1R, 2R)-norpseudoephedrine and a midbody thereof. The method comprises the following steps: in the reaction process in the first step, by taking a carrot as a medium, carrying out bio-transforming on 2-oximido-1-phenylacetone and reducing into (R)-2-oximido-1-phenyl propyl alcohol; in the second step, reducing (R)-2-oximido-1-phenyl propyl alcohol into a mixture of (1R, 2S)-norephedrine and (1R, 2R)-norpseudoephedrine; adding a chiral reliquid reagent (R)-O-acetyl mandelic acid and decomposing, thereby acquiring an optical pure (1R, 2S)-norephedrine and (1R, 2R)-norpseudoephedrine monomeric compound.