Structural Formula Vector Image
Title: Epinephrine
CAS Registry Number: 51-43-4
CAS Name: 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
Additional Names: (-)-3,4-dihydroxy-a-[(methylamino)methyl]benzyl alcohol; l-1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanol; l-3,4-dihydroxy-1-[1-hydroxy-2-(methylamino)ethyl]benzene; l-methylaminoethanolcatechol; adrenaline; levorenin
Trademarks: Anapen (Celltech); EpiPen (Dey); Primatene Mist (Wyeth); Sus-phrine (Forest)
Molecular Formula: C9H13NO3
Molecular Weight: 183.20
Percent Composition: C 59.00%, H 7.15%, N 7.65%, O 26.20%
Literature References: Endogenous catcholamine with combined a- and b-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Isoln from animal adrenal glands: Takamine, J. Soc. Chem. Ind. 20, 746 (1901); Aldrich, Am. J. Physiol. 5, 457 (1901). Synthesis of dl-form: Stolz, Ber. 37, 4149 (1904); Payne, Ind. Chem. 37, 523 (1961). Historic review of syntheses: Loewe, Arzneim.-Forsch. 4, 583 (1954). Resolution of dl-form: Flächer, Z. Physiol. Chem. 58, 189 (1908). Configuration: Pratesi et al., J. Chem. Soc. 1958, 2069. Acute toxicity: A. M. Lands et al., J. Pharmacol. Exp. Ther. 90, 110 (1947). HPLC determn in plasma and urine: C. R. Benedict, J. Chromatogr. 385, 369 (1987). Comprehensive description: D. H. Szulczewski, W.-H. Hong, Anal. Profiles Drug Subs. 7, 193-229 (1978). Physiologic review: Malmejac, Physiol. Rev. 44, 186 (1964). Review of biosynthesis: L. A. Pohorecky, R. J. Wurtman, Pharmacol. Rev. 23, 1-35 (1971); of pharmacology and clinical use in cardiopulmonary resuscitation: N. A. Paradis, E. M. Koscove, Ann. Emerg. Med. 19, 1288-1301 (1990); P. Hebert et al., J. Emerg. Med. 9, 487-495 (1991). Review of use in anaphylaxis: A. P. C. McLean-Tooke et al., Br. Med. J. 327, 1332-1335 (2003).
Properties: Minute crystals, gradually browning on exposure to light and air. mp 211-212°. mp ~215° (dec) when rapidly heated. [a]D25 -50.0° to -53.5° (in 0.6N HCl). Very slightly sol in water, alc. Readily sol in aq solns of mineral acids, NaOH, and KOH. Insol in aq solns of ammonia and of the alkali carbonates. Insol in chloroform, ether, acetone, oils. LD50 i.p. in mice: 4 mg/kg (Lands).
Melting point: mp 211-212°; mp ~215° (dec) when rapidly heated
Optical Rotation: [a]D25 -50.0° to -53.5° (in 0.6N HCl)
Toxicity data: LD50 i.p. in mice: 4 mg/kg (Lands)
Derivative Type: Hydrochloride
CAS Registry Number: 55-31-2
Trademarks: Adrenalin (Monarch); Epifrin (Allergan); Glaucon (Alcon); Suprarenin (Aventis)
Molecular Formula: C9H13NO3.HCl
Molecular Weight: 219.67
Percent Composition: C 49.21%, H 6.42%, N 6.38%, O 21.85%, Cl 16.14%
Derivative Type: d-Bitartrate
CAS Registry Number: 51-42-3
Trademarks: Asthmahaler (Menley & James); Medihaler-Epi (3M Pharma)
Molecular Formula: C9H13NO3.C4H6O6
Molecular Weight: 333.29
Percent Composition: C 46.85%, H 5.75%, N 4.20%, O 43.20%
Properties: Crystals, mp 147-154° (some dec). Darkens slowly on exposure to air and light. One gram dissolves in about 3 ml water. Slightly sol in alc.
Melting point: mp 147-154° (some dec)
Derivative Type: dl-Form
CAS Registry Number: 329-65-7
Additional Names: Racepinephrine
Properties: Sparingly sol in water, alcohol.
Derivative Type: dl-Form hydrochloride
CAS Registry Number: 329-63-5
Trademarks: Vaponefrin (Novartis)
Properties: Crystals from alcohol, mp 157°. Readily sol in water; sparingly sol in abs alc.
Melting point: mp 157°
Therap-Cat: Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.
Therap-Cat-Vet: Vasoconstrictor; cardiostimulant.
Keywords: a-Adrenergic Agonist; ?Adrenergic Agonist; Antiglaucoma; Bronchodilator; Ephedrine Derivatives; Decongestant; Mydriatic.

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