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Substance Name: Epinephrine bitartrate [USP:JAN]
RN: 51-42-3
UNII: 30Q7KI53AK
InChIKey: YLXIPWWIOISBDD-NDAAPVSOSA-N

Note

  • The active sympathomimetic hormone from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics.

Molecular Formula

  • C9-H13-N-O3.C4-H6-O6

Molecular Weight

  • 333.2911
 

Classification Codes

  • Adrenergic (Ophthalmic)
  • Drug / Therapeutic Agent
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Epinephrine bitartrate [USP:JAN]

Synonyms

  • (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol (+)-tartrate (1:1) salt
  • (-)-Adrenaline acid tartrate
  • (-)-Adrenaline bitartrate
  • (-)-Adrenaline hydrogen tartrate
  • (-)-Adrenaline tartrate
  • (-)-Epinephrine (+)-bitartrate
  • (-)-Epinephrine bitartrate
  • (R)-(-)-Epinephrine bitartrate
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:1) (salt)
  • Adrenaline acid tartrate
  • Adrenaline acid tartrate, l-
  • Adrenaline bitartrate
  • Adrenaline hydrogen tartrate
  • Asmatane Mist
  • Bronitin
  • Bronitin Mist
  • Bronkaid Mist Suspension
  • EINECS 200-097-1
  • Epinephrine bitartrate
  • Epinephrine d-bitartrate
  • Epinephrine hydrogen tartrate
  • Epinephrine tartrate
  • Epitrate
  • l-Adrenaline bitartrate
  • l-Adrenaline d-bitartrate
  • l-Adrenaline hydrogen tartrate
  • L-Adrenaline tartrate
  • l-Epinephrine bitartrate
  • l-Epinephrine d-bitartrate
  • l-Epinephrine tartrate
  • Medihaler-Epi
  • Primatene Mist Suspension
  • Suprarenin
  • UNII-30Q7KI53AK

Systematic Names

  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:1) (salt)
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (theta)-, (theta-(theta,theta))-2,3-dihydroxybutanedioate (1:1) (salt)
  • Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-, tartrate (1:1), (+)-
  • Epinephrine hydrogen tartrate

Mixture Names

  • Asthmahaler
  • E-Pilo
  • Vivacaine

Registry Numbers

CAS Registry Number

  • 51-42-3

FDA UNII

  • 30Q7KI53AK

Other Registry Numbers

  • 16536-89-3
  • 3506-10-3
  • 5502-52-3
  • 8028-06-6

System Generated Number

  • 0000051423

Molecular Formulas

Molecular Formula

  • C9-H13-N-O3.C4-H6-O6

Molecular Formula Fragments

  • C4-H6-O6
  • C9-H13-N-O3
  • COMPONENT

Structure Descriptors

InChI

1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1

InChIKey

YLXIPWWIOISBDD-NDAAPVSOSA-N

Smiles

CNC[C@@H](c1ccc(c(c1)O)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 800mg/kg (800mg/kg) CARDIAC: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

GASTROINTESTINAL: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
mouse LD50 intraperitoneal 7800ug/kg (7.8mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 43, 1972.
mouse LD50 intravenous 1780ug/kg (1.78mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 81, Pg. 269, 1944.
mouse LD50 oral 4mg/kg (4mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 49, 1972.
mouse LD50 subcutaneous 11100ug/kg (11.1mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 55, Pg. 73, 1984.
rat LD50 intravenous 82ug/kg (0.082mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 155, 1962.
rat LD50 subcutaneous 8300ug/kg (8.3mg/kg)   Drugs in Japan Vol. 6, Pg. 122, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 147-154 deg C   EXP
log P (octanol-water) -5.230 (none)   EST
Water Solubility 3.33E+05 mg/L   EXP
Vapor Pressure 1.87E-16 mm Hg 25 EST
Henry's Law Constant 1.96E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.51E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.