L-(-)-Ephedrine

L-(-)-Ephedrine Basic information
Product Name:L-(-)-Ephedrine
Synonyms:Benzyl alcohol,alpha-(1-aminoethyl)-;Fenilpropanolamina;l-phenylpropanolamine;Mydriatin;Norephedrine, (-)-;Propadrine;USAF cs-6;(-)-benzylalcoho
CAS:492-41-1
MF:C9H13NO
MW:151.21
EINECS:207-755-7
Product Categories:Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
Mol File:492-41-1.mol
L-(-)-Ephedrine Structure
L-(-)-Ephedrine Chemical Properties
Melting point 51-53 °C(lit.)
alpha -41 º (c=7, 1M HCl)
Boiling point 273.23°C (rough estimate)
density 1.0406 (rough estimate)
refractive index 1.5380 (estimate)
Fp >230 °F
storage temp. 2-8°C
pka9.958(at 10℃)
form A solid
Stability:Stable. Incompatible with strong oxidizing agents. May discolour on exposure to light.
CAS DataBase Reference492-41-1(CAS DataBase Reference)
NIST Chemistry ReferencePhenylpropanolamine(492-41-1)
EPA Substance Registry SystemBenzenemethanol, .alpha.-[(1S)-1-aminoethyl]-, (.alpha.R)- (492-41-1)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 26
WGK Germany 3
RTECS RC2275000
3-8-10
Hazard Note Harmful
ToxicityLD50 orl-rat: 1538 mg/kg BCFAAI 109,132,70
MSDS Information
ProviderLanguage
SigmaAldrich English
L-(-)-Ephedrine Usage And Synthesis
DescriptionThis 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 Propertieswhite powder
UsesA metabolite of Phenmetrazine.
DefinitionChEBI: (-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid.
Safety ProfileA 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.
ReferencesKanao., 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)
L-(-)-Ephedrine Preparation Products And Raw materials
Raw materialsD-(+)-Norephedrine-->CATHINE HYDROCHLORIDE-->Benzaldehyde-->Nitroethane
Preparation ProductsNorpseudoephedrine hydrochloride
Tag:L-(-)-Ephedrine(492-41-1) Related Product Information
6-Aminocaproic acid ALTRENOGEST Glycine Tris(hydroxymethyl)aminomethane PHENYL VALERATE 1-Propanol (1R,2S)-(-)-EPHEDRINE NITRATE tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE L-N-METHYLEPHEDRINE HYDROCHLORIDE, 99 (-)-BICUCULLINE METHOBROMIDE Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate L-(-)-Ephedrine (-)-EPHEDRINE,EPHEDRINE,EPHEDRINE BASE ANHYDROUS,Ephedrine Hydrochlorid, Ephetonin, sanedrine,(1R,1S)-(-)-EPHEDRINE,(1R,2S)-(-)-EPHEDRINE 1R,2S-(-)-Norephedrine hydrochloride (+)-Bicuculline (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Phenylacetic acid