Epinephrine

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.
Epiquinidine Epiquinine Epirizole Epithiazide EPN

Epinephrine
Epinephrine structure.svg
Systematic (IUPAC) name
(R)-4-(1-hydroxy-
2-(methylamino)ethyl)benzene-1,2-diol
Clinical data
Pregnancy cat. C (US)
Legal status Prescription Only (S4) (AU) POM (UK) OTC (US)
Routes IV, IM, endotracheal, IC, Nasal
Pharmacokinetic data
Bioavailability Nil (oral)
Metabolism adrenergic synapse (MAO and COMT)
Half-life 2 minutes
Excretion Urine
Identifiers
CAS number 51-43-4 YesY
ATC code A01AD01 B02BC09 C01CA24 R01AA14 R03AA01 S01EA01
PubChem CID 5816
IUPHAR ligand 479
DrugBank DB00668
ChemSpider 5611 YesY
UNII YKH834O4BH YesY
KEGG D00095 YesY
ChEBI CHEBI:28918 YesY
ChEMBL CHEMBL679 YesY
Chemical data
Formula C9H13NO3 
Mol. mass 183.204 g/mol
 YesY (what is this?)  (verify)

Epinephrine (also known as adrenaline, adrenalin, or 4,5-β-trihydroxy-N-methylphenethylamine) is a hormone and a neurotransmitter.[1] The investigation of the pharmacology of epinephrine made a major contribution to the understanding of the autonomic system and the function of the sympathetic system. Epinephrine remains a useful medicine for several emergency indications. This is despite its non-specific action on adrenoceptors and the subsequent development of multiple selective medicines that target subtypes of the adrenoceptor. The word adrenaline is used in common parlance to denote increased activation of the sympathetic system associated with the energy and excitement of the flight, fight and fright response, even though this is physiologically inaccurate. [2][3] The influence of adrenaline is mainly limited to a metabolic effect and bronchodilator effect on organs devoid of direct sympathetic innervation.[4][5]

In chemical terms, epinephrine is one of a group of monoamines called the catecholamines. It is produced in some neurons of the central nervous system, and in the chromaffin cells of the adrenal medulla from the amino acids phenylalanine and tyrosine.[6]