3608. Ephedrine

Nomenclature

CAS number: 299-42-3
(αR)-α-[(1S)-1-(Methylamino)ethyl]benzenemethanol; (1R,2S)-2-methylamino-1-phenylpropan-1-ol; l-erythro-2-(methylamino)-1-phenylpropan-1-ol; l-ephedrine.
C10H15NO; mol wt 165.23.
C 72.69%, H 9.15%, N 8.48%, O 9.68%.

Description and references

α- and β-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. Sp"ath, R. G"ohring, 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).

Chemical structure

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.

Derivative

Hydrochloride.

Nomenclature

CAS number: 50-98-6
Caniphedrin (Streuli).
C10H15NO.HCl; mol wt 201.69.
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°. [α]D25 -33 to -35.5° (c = 5). Freely sol in water; sol in alcohol. Practically insol in ether.

Derivative

Sulfate.

Nomenclature

CAS number: 134-72-5
Isofedrol (Boehringer, Mann.).
(C10H15NO)2.H2SO4; mol wt 428.54.
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). [α]D25 -30 to -32.5° (c = 5). Freely sol in water; sparingly sol in alcohol.

Derivative

dl-Form.

Nomenclature

CAS number: 90-81-3
Racemic ephedrine; racephedrine.

Properties

Crystals from chloroform-petr ether, mp 75°. Sol in water, alcohol, ether, chloroform, oils.

Derivative

dl-Form hydrochloride.

Nomenclature

CAS number: 134-71-4
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.

Derivative

(+)-threo-Form see Pseudoephedrine.

Therapeutic Category

Bronchodilator.

Therapeutic Category (Veterinary)

Bronchodilator; in treatment of urinary incontinence.

Keywords

α-Adrenergic Agonist; β-Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Decongestant