Section 1: Identification
Name: EPINEPHRINE
Uses:
- Epinephrine may be applied topically to control superficial bleeding from arterioles or capillaries in the skin, mucous membrane, or other tissues. Bleeding from larger vessels is not controllable by topical application of epinephrine.[McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 626]
- Epinephrine has been used to relax uterine musculature and inhibit uterine contractions in premature labor; however the cardiovascular effects and other adverse effects limit the usefullness of the drug for this purpose. Some manufacturers state that epinephrine injection is contraindicated during the second stage of labor.[McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 626]
- Drug of choice for emergency treatment of severe allergic reactions to insect stings or bites, foods, drugs, and other allergens.[Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 1024]
- Used in the treatment of idiopathic or exercise-induced anaphylaxis[Thomson Health Care Inc.; Physicians' Desk Reference 63 ed., Montvale, NJ 2009, p. 1024]
- Medicine (vasoconstrictor).[Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 506]
- Therapeutic Category: Bronchodilator; cardiostimulant; mydriatic; antiglaucoma[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
- Therapeutic Category (VET): Vasoconstrictor; cardiostimulant[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
- MEDICATION
- MEDICATION (VET)
Section 2: Hazard(s) Identification
Signal Word(s):
Warning
EPA Hazardous Waste Number:
- P042; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
Section 3: Composition/Information on Ingredients
Name: EPINEPHRINE
CAS Registry Number: 51-43-4
UNII: YKH834O4BH
Synonyms:
- Adnephrine[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3663]
- Adrenal[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3663]
- 1-Adrenalin[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- Adrenaline
- 1,2-Benzenediol, 4-(1-Hydroxy-2-(methylamino)ethyl)-, (R)-
- benzyl alcohol, 3,4-Dihydroxy-alpha-((methylamino)methyl)-, (-)-
- 3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- Epinefrina (Spanish)[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- Epinephran[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3663]
- (-)-Epinephrine[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- (R)-Epinephrine[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- 1-Epinephrine[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
- 4-((1R)-1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
- (R)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol (9CI)[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3664]
- l-Methylaminoethanolcatechol[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
- Vasoconstrictor[U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/8209]
Section 4: First-Aid Measures
Section 5: Fire-Fighting Measures
Section 6: Accidental Release Measures
Section 7: Handling and Storage
Section 8: Exposure Controls/Personal Protection
Section 9: Physical and Chemical Properties
Brown (in air)[Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-228]
Minute crystals, gradually browning on exposure to liaght and air[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Light brown or nearly white crystalline powder[Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 505]
Colorless microcrystals[Pugsley TA; Kirk-Othmer Encyclopedia of Chemical Technology. (2001). NY, NY: John Wiley & Sons; Epinephrine and Norepinephrine. Online Posting Date: Dec 4, 2000.]
White to nearly white, microcrystalline powder or granules.[McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 625]
Odorless[Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 505]
211.5 deg C[Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-228]
183.20[Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-228]
pKa = 8.28[Volpi A, Toffoli F; Bull Chim Farm 118: 594-609 (1979)]
pKa1 = 9.49 (phenol); pKa2 = 11.28 (amine); pKa3 = 13.07 (phenol) (est)[SPARC; pKa/property server. Ver 4.2 Mar, 2008. Available from, as of Mar 5, 2010: http://ibmlc2.chem.uga.edu/sparc/]
log Kow = -2.59[Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 62]
Very slightly soluble in alcohol. Readily soluble in aqueous solutions of mineral acids, NaOH, and KOH. Insoluble in aqueous solutions of ammonia and of the alkali carbonates. Insoluble in chloroform, ether, acetone, oils.[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Very slightly soluble in alcohol.[McEvoy, G.K. (ed.). AHFS Drug Information 90. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1990 (Plus Supplements 1990)., p. 625]
Insoluble in ethanol; soluble in acetic acid[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
In water, 180 mg/L at 20 deg C[Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 597]
Specific optical rotation = -50 deg to -53.3 deg at 25 deg C/D (in 0.6N HCl)[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Specific optical rotation = -53 deg at 20 deg C/D (aqueous HCl)[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
Absorption spectrum in 0.1M HCl: lambda max 221 nm (epsilon about 6100); lambda max 280 nm (epsilon about 2700)[Pugsley TA; Kirk-Othmer Encyclopedia of Chemical Technology. (2001). NY, NY: John Wiley & Sons; Epinephrine and Norepinephrine. Online Posting Date: Dec 4, 2000.]
IR: 1566 (Coblentz Society Spectral Collection)[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
UV: 1512 (Absorption Spectra in the UV and visible Regions, Academic Press, New York)[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
MASS: 24257 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 956 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
7.37X10-8 mm Hg at 25 deg C (est)[US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of Sept 2, 2009: http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm]
MP: 211-212 deg C, approximately 215 deg C with decomposition when heated rapidly[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Crystals. MP: 147-154 deg C (some decomposition); darkens slowly on exposure to air and light; 1 g dissolves in about 3 mL water; slightly sol in alcohol. /l-form d-Bitartrate/[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Sparingly soluble in water, alcohol /dl-Epinephrine/[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
Crystals from alcohol, mp 157 deg C. Readily soluble in water; sparingly soluble in absolute alcohol /dl-Epinephrine hydrochloride/[O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 618]
IR: 7393 (Sadtler Research Laboratories Spectral Collection) /Adrenaline/[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
MASS: 956 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63). /Adrenaline/[Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 907]
Deteriorates rapidly on expsoure to air, light, heat, and alkalies. Copper, iron, and zinc destroy its activity. Slowly forms and inactive sulfonate in solution with sulfite or bisulfite. The red color that forms when neutral or alkaline solutions are exposed to air is caused by adrenochrome.[Pugsley TA; Kirk-Othmer Encyclopedia of Chemical Technology. (2001). NY, NY: John Wiley & Sons; Epinephrine and Norepinephrine. Online Posting Date: Dec 4, 2000.]
Henry's Law constant = 7.06X10-19 atm-cu m/mol at 25 deg C (est)[US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of Sept 2, 2009: http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm]
Hydroxyl radical reaction rate constant = 1.38X10-10 cu cm/molec-sec at 25 deg C (est)[US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of Sept 2, 2009: http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm]
Section 10: Stability and Reactivity
Chemical stability
- In some commercially available injections, the air has been replaced with nitrogen to avoid oxidation. Withdrawal of doses from multiple-dose vials introduces air into the vials, subjecting the remaining epinephrine to oxidation. Oxidation of the drug imparts first a pink, then a brown color; epinephrine preparations must not be used if they have a pinkish or darker than slightly yellow color or contain a precipitate.[American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 1394]
Other
- When heated to decomposition it emits toxic fumes of /nitrogen oxides/.[Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3664]
Section 11: Toxicological Information
All references are peer reviewed