3619. Epinephrine

Nomenclature

CAS number: 51-43-4
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (-)-3,4-dihydroxy-α-[(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; Anapen (Celltech); EpiPen (Dey); Primatene Mist (Wyeth); Sus-phrine (Forest).
C9H13NO3; mol wt 183.20.
C 59.00%, H 7.15%, N 7.65%, O 26.20%.

Description and references

Endogenous catcholamine with combined α- and β-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: Fl"acher, 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).

Chemical structure

Properties

Minute crystals, gradually browning on exposure to light and air. mp 211-212°. mp ≈215° (dec) when rapidly heated. [α]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).

Derivative

Hydrochloride.

Nomenclature

CAS number: 55-31-2
Adrenalin (Monarch); Epifrin (Allergan); Glaucon (Alcon); Suprarenin (Aventis).
C9H13NO3.HCl; mol wt 219.67.
C 49.21%, H 6.42%, N 6.38%, O 21.85%, Cl 16.14%.

Derivative

d-Bitartrate.

Nomenclature

CAS number: 51-42-3
Asthmahaler (Menley & James); Medihaler-Epi (3M Pharma).
C9H13NO3.C4H6O6; mol wt 333.29.
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.

Derivative

dl-Form.

Nomenclature

CAS number: 329-65-7
Racepinephrine.

Properties

Sparingly sol in water, alcohol.

Derivative

dl-Form hydrochloride.

Nomenclature

CAS number: 329-63-5
Vaponefrin (Novartis).

Properties

Crystals from alcohol, mp 157°. Readily sol in water; sparingly sol in abs alc.

Therapeutic Category

Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.

Therapeutic Category (Veterinary)

Vasoconstrictor; cardiostimulant.

Keywords

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