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Substance Name: Epinephrine [USP:INN:BAN:JAN]
RN: 51-43-4
UNII: YKH834O4BH
InChIKey: UCTWMZQNUQWSLP-VIFPVBQESA-N

Note

  • The active sympathomimetic hormone from the ADRENAL MEDULLA. 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

Molecular Weight

  • 183.206
 

Classification Codes

Classification Codes

  • Adrenergic (Vasoconstrictor)
  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-Agonists
  • Adrenergic beta-Agonists
  • Anti-Asthmatic Agents
  • Autonomic Agents
  • Bronchodilator Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Mydriatics
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Respiratory System Agents
  • Sympathomimetics
  • Vasoconstrictor Agents

Superlist Classification Code

  • Reportable Quantity (RQ) = 1000 lb

Names and Synonyms

Name of Substance

  • Epinephrine
  • Epinephrine [USP:INN:BAN:JAN]

MeSH Heading

  • Epinephrine

Synonyms

  • (-)-(R)-Epinephrine
  • (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
  • (R)-Adrenaline
  • (R)-Epinephrine
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-
  • 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
  • 1-Adrenalin
  • 1-Epinephrine
  • 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
  • Adnephrine
  • Adrenaclick
  • Adrenal
  • Adrenalin
  • Adrenalin in Oil
  • Adrenalin-Medihaler
  • Adrenalina
  • Adrenalina [DCIT]
  • Adrenaline
  • Adrenalinum
  • Adrenamine
  • Adrenapax
  • Adrenasol
  • Adrenine
  • Adrenodis
  • Adrenohorma
  • Adrenosan
  • Adrenutol
  • Adrin
  • AI3-19015
  • Antiasthmatique
  • Asmatane Mist
  • Asthma meter mist
  • Asthma-nefrin
  • Astmahalin
  • Astminhal
  • Auvi-Q
  • Auvi-Q auto-injector
  • Balmadren
  • Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-
  • Bernarenin
  • Biorenine
  • Bosmin
  • Brevirenin
  • Bronkaid
  • Bronkaid Mist
  • CCRIS 4812
  • Chelafrin
  • Corisol
  • Drenamist
  • Dylephrin
  • Dyspne-inhal
  • EINECS 200-098-7
  • Epi E Z Pen jr
  • Epifrin
  • Epinefrin
  • Epinefrin [Czech]
  • Epinefrina
  • Epinefrina [INN-Spanish]
  • Epinephran
  • Epinephrine
  • Epinephrinum
  • Epinephrinum [INN-Latin]
  • Epipen
  • Epipen E Z Pen
  • Epipen jr.
  • Epirenan
  • Esphygmogenina
  • Exadrin
  • Glaucon
  • Glaucosan
  • Glycirenan
  • Haemostasin
  • Haemostatin
  • Hektalin
  • Hemisine
  • Hemostasin
  • Hemostatin
  • HSDB 4289
  • Hypernephrin
  • Hyporenin
  • Intranefrin
  • Isoptoepinal
  • Kidoline
  • l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
  • l-Adrenaline
  • l-Epinephrine
  • l-Epinephrine (synthetic)
  • l-Epirenamine
  • Levoepinephrine
  • Levorenin
  • Levorenine
  • Lyophrin
  • Methylaminoethanolcatechol
  • Methylarterenol
  • Mucidrina
  • Myosthenine
  • Mytrate
  • Nephridine
  • Nieraline
  • NSC 62786
  • Paranephrin
  • Primatene Mist
  • R-(-)-Epinephrine
  • RCRA waste number P042
  • Renaglandin
  • Renaleptine
  • Renalina
  • Renoform
  • Renostypticin
  • Scurenaline
  • Simplene
  • Sindrenina
  • Soladren
  • Sphygmogenin
  • Stryptirenal
  • Styptirenal
  • Supracapsulin
  • Supradin
  • Supranefran
  • Supranephrane
  • Supranephrine
  • Supranol
  • Suprarenaline
  • Suprel
  • Sus-Phrine
  • Sus-phrine sulfite-free
  • Symjepi
  • Sympathin I
  • Takamina
  • Takamine
  • Tokamina
  • Tonogen
  • Twinject
  • Twinject 0.15
  • Twinject 0.3
  • UNII-YKH834O4BH
  • Vaponefrin
  • Vasoconstrictine
  • Vasodrine
  • Vasotonin

Systematic Names

  • 1,2-Benzenediol, 4-((1R)-1-hydroxy-2-(methylamino)ethyl)-
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (theta)-
  • Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-
  • Epinephrine

Superlist Names

  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-
  • Epinephrine
  • RCRA waste no. P042

Mixture Name

  • Citanest forte

Registry Numbers

CAS Registry Number

  • 51-43-4

FDA UNII

  • YKH834O4BH

Other Registry Number

  • 51028-73-0

System Generated Number

  • 0000051434

Structure Descriptors

InChI

1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1

InChIKey

UCTWMZQNUQWSLP-VIFPVBQESA-N

Smiles

c1(cc(c(O)cc1)O)[C@H](CNC)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 500ug/kg (0.5mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
cat LDLo subcutaneous 20mg/kg (20mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
dog LD50 intravenous 100ug/kg (0.1mg/kg)   Drugs in Japan Vol. 6, Pg. 120, 1982.
dog LD50 subcutaneous 5mg/kg (5mg/kg)   Drugs in Japan Vol. 6, Pg. 120, 1982.
dog LDLo parenteral 5ug/kg (0.005mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 1, Pg. 189, 1968.
guinea pig LDLo intravenous 100ug/kg (0.1mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
guinea pig LDLo subcutaneous 800ug/kg (0.8mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
infant TDLo multiple routes 625ug/kg/I (0.625mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Southern Medical Journal. Vol. 78, Pg. 874, 1985.
man LDLo subcutaneous 7ug/kg (0.007mg/kg) CARDIAC: OTHER CHANGES

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
Annals of Emergency Medicine. Vol. 28, Pg. 725, 1996.
man TDLo intramuscular 2ug/kg (0.002mg/kg) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990.
man TDLo intravenous 16ug/kg (0.016mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: CHANGE IN RATE
American Journal of Emergency Medicine. Vol. 5, Pg. 64, 1987.
man TDLo intravenous 285ug/kg (0.285mg/kg)   American Journal of Emergency Medicine. Vol. 7, Pg. 485, 1989.
man TDLo intravenous 285ug/kg (0.285mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE American Journal of Emergency Medicine. Vol. 7, Pg. 485, 1989.
man TDLo intravenous 3mg/kg (3mg/kg) VASCULAR: CONTRACTION (ISOLATED TISSUES) American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990.
man TDLo oral 77mg/kg (77mg/kg) BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Emergency Medicine. Vol. 19, Pg. 671, 1990.
man TDLo subcutaneous 8571ng/kg/80M (0.008571mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION American Heart Journal. Vol. 111, Pg. 1193, 1986.
man TDLo subcutaneous 43ug/kg (0.043mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Annals of Emergency Medicine. Vol. 19, Pg. 680, 1990.
mouse LD50 intraperitoneal 4mg/kg (4mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 110, 1947.
mouse LD50 intravenous 217ug/kg (0.217mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976.
mouse LD50 subcutaneous 1470ug/kg (1.47mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 202, Pg. 658, 1943.
mouse LDLo oral 50mg/kg (50mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
mouse LDLo unreported 10mg/kg (10mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 162, Pg. 46, 1931.
rabbit LD50 intravenous 50ug/kg (0.05mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.
rabbit LD50 subcutaneous 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.
rabbit LDLo oral 30mg/kg (30mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
rat LD50 intramuscular 3500mg/kg (3500mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 105, 1973.
rat LD50 intravenous 150ug/kg (0.15mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 41, Pg. 365, 1931.
rat LD50 skin 62mg/kg (62mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(4), Pg. 30, 1964.
rat LD50 subcutaneous 5mg/kg (5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.
rat LDLo intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 268, 1946.
rat LDLo oral 30mg/kg (30mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948.
women TDLo intravenous 6ug/kg (0.006mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) British Medical Journal. Vol. 286, Pg. 519, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 211.5 deg C   EXP
pKa Dissociation Constant 8.59 (none) 25 EXP
log P (octanol-water) -1.37E+00 (none)   EXP
Water Solubility 180 mg/L 20 EXP
Vapor Pressure 7.37E-07 mm Hg 25 EST
Henry's Law Constant 7.06E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.38E-10 cm3/molecule-sec 25 EST

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