Ephedrine
Title: Ephedrine
CAS Registry Number: 299-42-3
CAS Name: (aR)-a-[(1S)-1-(Methylamino)ethyl]benzenemethanol
Additional Names: (1R,2S)-2-methylamino-1-phenylpropan-1-ol; L-erythro-2-(methylamino)-1-phenylpropan-1-ol; l-ephedrine
Molecular Formula: C10H15NO
Molecular Weight: 165.23
Percent Composition: C 72.69%, H 9.15%, N 8.48%, O 9.68%
Literature References: a- and b-Adrenergic agonist. Occurs in plants of the genus Ephedra (Ephedraceae) known in traditional medicine as Ma Huang. Isoln from E. vulgaris: Nagai, Chem. Zentralbl. 59, 130 (1888). Syntheses: E. Späth, R. Göhring, Monatsh. Chem. 41, 319 (1920); R. H. F. Manske, T. B. Johnson, J. Am. Chem. Soc. 51, 580, 1906 (1929). Stereochemistry: K. Freudenberg et al., ibid. 54, 234 (1932); K. Freudenberg, F. Nikolai, Ann. 510, 223 (1934). Properties of crystalline forms: E. E. Moore, D. L. Tabern, J. Am. Pharm. Assoc. 24, 211 (1935). Symposium on sympathomimetic agents: Ind. Eng. Chem. 37, 116-148 (1945). Toxicity: M. D. Fairchild, G. A. Alles, J. Pharmacol. Exp. Ther. 158, 135 (1967). Electrophoretic determn in urine: M. Chicharro et al., J. Chromatogr. 622, 103 (1993). HPLC determn in Ma Huang: B. J. Gurley et al., J. Pharm. Sci. 87, 1547 (1998). Clinical pharmacokinetics of botanical ephedrine: eidem, Ther. Drug Monit. 20, 439 (1998). Review of use as bronchodilator: M. M. Weinberger, Pediatr. Clin. North Am. 22, 121-127 (1975).
Properties: Waxy solid, crystals or granules. Gradually dec on exposure to light. Anhydr material is hygroscopic, mp 38.1°. Also occurs as the hemihydrate, mp 40°. bp745 260°. Sol in water, alcohol, chloroform, ether. Keep well closed in a cool place.
Melting point: mp 38.1°; mp 40°
Boiling point: bp745 260°
 
Derivative Type: Hydrochloride
CAS Registry Number: 50-98-6
Trademarks: Caniphedrin (Streuli)
Molecular Formula: C10H15NO.HCl
Molecular Weight: 201.69
Percent Composition: C 59.55%, H 8.00%, N 6.94%, O 7.93%, Cl 17.58%
Properties: Fine, white, odorless crystals or powder, affected by light, mp 217-220°. [a]D25 -33 to -35.5° (c = 5). Freely sol in water; sol in alcohol. Practically insol in ether.
Melting point: mp 217-220°
Optical Rotation: [a]D25 -33 to -35.5° (c = 5)
 
Derivative Type: Sulfate
CAS Registry Number: 134-72-5
Trademarks: Isofedrol (Boehringer, Mann.)
Molecular Formula: (C10H15NO)2.H2SO4
Molecular Weight: 428.54
Percent Composition: C 56.05%, H 7.53%, N 6.54%, O 22.40%, S 7.48%
Properties: Fine, white, odorless crystals or powder. Darkens on exposure to light. mp 245° (dec). [a]D25 -30 to -32.5° (c = 5). Freely sol in water; sparingly sol in alcohol.
Melting point: mp 245° (dec)
Optical Rotation: [a]D25 -30 to -32.5° (c = 5)
 
Derivative Type: dl-Form
CAS Registry Number: 90-81-3
Additional Names: Racemic ephedrine; racephedrine
Properties: Crystals from chloroform-petr ether, mp 75°. Sol in water, alcohol, ether, chloroform, oils.
Melting point: mp 75°
 
Derivative Type: dl-Form hydrochloride
CAS Registry Number: 134-71-4
Additional Names: Racephedrine hydrochloride
Properties: Crystals from alcohol-acetone, mp 189°. One gram dissolves in 4 ml water, in about 40 ml of 95% alc at 20°. Practically insol in ether. pH about 6.
Melting point: mp 189°
 
Derivative Type: (+)-threo-Form see Pseudoephedrine
 
Therap-Cat: Bronchodilator.
Therap-Cat-Vet: Bronchodilator; in treatment of urinary incontinence.
Keywords: a-Adrenergic Agonist; ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Decongestant.

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