Identification and Related Records
- 【CAS Registry number】
- 【Molecular Formula】
- C9H13NO3 (Products with the same molecular formula)
Chemical and Physical Properties
- Brown (in air)
Minute crystals, gradually browning on exposure to liaght and air
Light brown or nearly white crystalline powder
White to nearly white, microcrystalline powder or granules.
- Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Light sensitive.
- 【Spectral properties】
- Specific optical rotation = -50 deg to -53.3 deg at 25 deg C/D (in 0.6N HCl)
Specific optical rotation = -53 deg at 20 deg C/D (aqueous HCl)
Absorption spectrum in 0.1M HCl: lambda max 221 nm (epsilon about 6100); lambda max 280 nm (epsilon about 2700)
IR: 1566 (Coblentz Society Spectral Collection)
UV: 1512 (Absorption Spectra in the UV and visible Regions, Academic Press, New York)
MASS: 24257 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 956 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
- 【Computed Properties】
- Molecular Weight:183.20442 [g/mol]
Rotatable Bond Count:3
Topological Polar Surface Area:72.7
Heavy Atom Count:13
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:4
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:13
Safety and Handling
Human poison by subcutaneous route. Experimental poison by ingestion, skin contact, subcutaneous, intraperitoneal, intravenous, and intramuscular routes. Human systemic effects: cardiomyopathy including infarction, arrhythmias. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Risk Statements: 23/24/25-52/53-36/37/38-33?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R33:Danger of cumulative effects.
Safety Statements: 36/37/39-45-61-26-23?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S33:Take precautionary measures against static discharges.
RIDADR: UN 2811 6.1/PG 2
WGK Germany :3
- EpiPen Auto-Injector
Asthma meter mist
Epinephrine injection is available in 1 mg/ml (1:1000), 0.1 mg/ml (1:10,000), and 0.5 mg/ml (1:2,000) solutions.
Epinephrine contains not less than 97.0% and not more than 100.5% of epinephrine, calculated on the dried basis.
Epinephrine Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Ophthalmic Solution 0.5% (of epinephrine) Epifrin (Allergan) Ophthalmic Solution 1% (of epinephrine) Epifrin (Allergan) Ophthalmic Solution 1% (of epinephrine) Glaucon (Alcon) Ophthalmic Solution 2% (of epinephrine) Epifrin (Allergan) Ophthalmic Solution 2% (of epinephrine) Glaucon (Alcon) Parenteral Injection 0.1 mg/mL (1:10,000) (of epinephrine) Epinephrine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 1 mg/mL (0.1% or 1:1000) (of epinephrine) Adrenalin Chloride Solution (Monarch) Parenteral Injection 1 mg/mL (0.1% or 1:1000) (of epinephrine) Epinephrine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name)
Epinephrine Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Nasal Solution 0.1% (1:1000) (of epinephrine) Adrenalin Chloride (Monarch) Parenteral injection 0.1 mg/mL (0.01% or 1:10,000) (of epinephrine) Epinephrine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 1 mg/mL (0.1% or 1:1000) (of epinephrine) Epinephrine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 1 mg/mL (0.1% or 1:1000) (of epinephrine) Adrenalin Chloride Solution (Monarch)
Epinephrine Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Inhalation Solution, for nebulization 1% (1:100) (of epinephrine) Adrenalin Chloride Solution (Monarch) Parenteral Injection 1 mg/mL (1:1000) (of epinephrine) Epinephrine injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 1 mg/mL (1:1000) (of epinephrine) EpiPen Auto-Injector [delivers a single 0.3-mg dose [0.3 mL]] (Dey) Parenteral Injection 0.1 mg/mL (1:10,000) (of epinephrine) Epinephrine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.5 mg/mL (1:2000) (of epinephrine) EpiPen Jr. Auto-Injector (Dey) Parenteral Injection 1 mg/mL (1:1000) (of epinephrine) Adrenalin Chloride Solution (Monarch)
Epinephrine Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Oral Inhalation Aerosol 220 ug/metered spray Epinephrine Mist (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Oral inhalation Aerosol 220 ug/metered spray (with fluorocarbon propellants) Primatene Mist (Wyeth)
- 【Exposure Standards and Regulations】
- Bronchodilator active ingredients. The active ingredients of the product consist of any of the following when used within the dosage limits established for each ingredient: Epinephrine and epinephrine bitartrate are included on this list.
Vasoconstrictor active ingredients. The active ingredient of the product consists of any of the following when used in the concentration or within the concentration range established for each ingredient. Epinephrine and epinephrine hydrochloride are included on this list.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl epinephrine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl epinephrine bitartrate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Epinephrine bitartrate/
?Adrenaline?, its cas register number is 51-43-4. It also can be called?(-)-(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 ; Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)- .It is a?off-white powder.It is a?is a hormone and neurotransmitter.
- 【Disposal Methods】
- SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number p042, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
1. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids. 2. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. 3. A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of Manufacturing
Reaction of pyrocatechol with chloroacetyl chloride, followed by reaction with methylamine, catalytic redn, and separation of racemic mixt with d-tartaric acid.
Isolation from animal adrenal glands.
From the adrenal glands of sheep and cattle or syntehtically from pyrocatecholU.S. Imports
(1977) 5.58X10+5 g (princpl custms dists)
(1979) 6.45X10+5 g (princpl custms dists
(1983) 5.49X10+7 gU.S. Production
(1975) Probably greater than 4.54x10+5 g
Biomedical Effects and Toxicity
- 【Pharmacological Action】
- - Drugs that selectively bind to and activate alpha adrenergic receptors.
- Drugs that selectively bind to and activate beta-adrenergic receptors.
- Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
- Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.
- Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
- Drugs used to cause constriction of the blood vessels.
- 【Therapeutic Uses】
- Adrenergic alpha-Agonists; Adrenergic beta-Agonists; Adrenergic Agonists; Bronchodilator Agents; Mydriatics; Sympathomimetics; Vasoconstrictor Agents
Epinephrine is the drug of choice in the emergency treatment of severe acute anaphylactic reactions including anaphylactic shock. Symptoms such as urticaria, pruritus, angioedema, and swelling of the lips, eyelids, and tongue which may result from reactions to drugs, sera, insect stings, food, or other allergens may be relieved by epinephrine. Epinephrine should be given to all patients with signs of systemic reactions, particularly hypotension, airway swelling, or definite breathing difficulty. Circulatory support during anaphylactic shock requires rapid volume resuscitation and vasopressor therapy to support blood pressure; epinephrine is the drug of choice for the treatment of both vasodilation/hypotension and cardiac arrest associated with anaphylaxis. /Included in US product label/
Epinephrine may be added to solutions of some local anesthetics to decrease the rate of vascular absorption of the anesthetic, thereby localizing anesthesia and prolonging the duration of anesthesia; the risk of systemic toxicity from the local anesthetic is also decreased. Epinephrine may be applied topically to control superficial bleeding from arterioles or capillaries in the skin, mucous membranes, or other tissues. Bleeding from larger vessels is not controllable by topical application of epinephrine. /Included in US product label/
Epinephrine is used for its a-adrenergic stimulatory effects to increase blood flow in advanced cardiovascular life support (ACLS) during cardiopulmonary resuscitation (CPR). The principal beneficial effects of the drug in patients with cardiac arrest result from increases in aortic diastolic blood pressure and in myocardial and cerebral blood flow during resuscitation. The value and safety of the beta-adrenergic effects of epinephrine are controversial because they may increase myocardial work and reduce subendocardial perfusion. Epinephrine remains a drug of choice and a high priority for ACLS in cardiac arrest to facilitate return of spontaneous circulation. /Included in US product label/
Epinephrine has been administered intra-arterially via the celiac artery, inferior mesenteric artery, or superior mesenteric artery to control hemorrhage in patients with severe GI bleeding and via the renal artery to control hemorrhage in patients with renal arterial bleeding. Epinephrine also has been injected into one renal artery prior to and during irradiation of the abdominal area involving both kidneys. The drug may protect the kidney from radiation nephritis by causing vasoconstriction which results in hypoxia. /Use not currently included in US product label/
Epinephrine has been given intra-arterially in conjunction with radiographic contrast media in arteriography. Epinephrine may improve visualization by causing vasoconstriction thereby reducing dilution of the contrast media in the blood. In addition, some tumors (especially if highly vascularized) may be better defined, apparently because epinephrine causes constriction and reduced filling of normal arteries surrounding the tumor while having minimal effect on the tumor vasculature. /Use not currently included in US product label/
Epinephrine and racepinephrine are used, generally as alternatives to inhaled, short-acting beta2-adrenergic agonists, as bronchodilators in the symptomatic treatment of bronchial asthma and reversible bronchospasm that may occur in association with chronic bronchitis, emphysema, and other obstructive pulmonary diseases. /Included in US product label/
Medication (Vet): epinephrine injection (1:1000): anaphylactoid shock, allergic reactions, bronchial asthma, and as a topical hemostat to control epistaxis and hemorrhage from small arterioles and capillaries. Epinephrine is sometimes successful in reinitiating the heart beat following cardiac arrest.
Applied topically to the eye, in ointment or as soln ... The ophthalmic preparations are used to decrease conjunctival and scleral inflammation and edema and to treat primary open-angle glaucoma. /Bitartrate USP/
Medication (Vet): dl-form hydrochloride: vasoconstrictor, cardiostimulant.
Epinephrine may be applied topically to the nasal mucosa as a decongestant; however, the drug has a short duration of action and rebound congestion frequently occurs. Other longer acting sympathomimetic agents such as oxymetazoline are more commonly used for this purpose. Epinephrine has been used as a decongestant when applied topically to the conjunctiva in patients with conjunctivitis resulting from nonspecific chronic irritation or allergy. However, the drug's effects in such cases usually lasted less than 1 hour and may have been followed by reactive hyperemia. /Included in US product label/
Epinephrine may be added to solutions of some local anesthetics such as procaine or lidocaine to decrease the rate of vascular absorption of the local anesthetic, thereby localizing anesthesia and prolonging the duration of anesthesia; the risk of systemic toxicity caused by the local anesthetic is also decreased, and bleeding in the operative field may be reduced. /Included in US product label/
Epinephrine is used locally to control superficial bleeding from arterioles and capillaries in the skin and mucous membranes of the eye, nose, mouth, throat or larynx, mainly during surgery. Bleeding from larger vessels is not controllable by topical application of epinephrine. The drug is especially useful in dental surgery. /Included in US product label/
In normal eyes, epinephrine is less effective than other mydriatics; however, the drug produces effective mydriasis when the permeability of the eye is increased during surgery. Epinephrine may be applied topically to the conjunctiva or injected into the anterior chamber of the eye during surgery to provide rapid mydriasis, especially in patients undergoing cataract extraction. Although generally contraindicated in patients with angle-closure glaucoma, epinephrine may be used to produce mydriasis for ophthalmoscopy in patients predisposed to angle closure. /Included in US product label/
In ophthalmology, topical epinephrine is used principally to reduce elevated IOP in the treatment of open-angle (chronic simple) glaucoma, generally as an adjunct to topical miotics, topical beta-adrenergic blocking agents, osmotic agents, and/or systemically administered carbonic anhydrase inhibitors. When used in conjunction with these agents, the effect of epinephrine in lowering IOP may be additive. Use of epinephrine in conjunction with miotics may reduce miosis and ciliary spasm that often occur when miotics are used alone. /Included in US product label/
- 【Biomedical Effects and Toxicity】
- Following topical application of radiolabeled epinephrine to the eye in rabbits, highest concentrations of the drug in tissues and fluids other than the eye occurred in the pituitary gland, with lower concentrations in the intestine, fat, adrenal gland, kidney, heart, lung, spleen, ovary, pancreas, liver, uterus, muscle, brain, and serum. In humans, systemically absorbed epinephrine crosses the placenta but not the blood-brain barrier. Systemically absorbed epinephrine distributes into milk.
Epinephrine is not effective after oral admin because it is rapidly conjugated and oxidized in GI mucosa and liver. Absorption from sc tissues occurs slowly because of local vasoconstriction ... Absorption is more rapid after im than after sc injection ... Epinephrine is rapidly inactivated in the body.
In a prospective, randomized, five-way crossover study in rabbits, ... plasma epinephrine concentrations /were measured/ before, and at intervals up to 180 min after epinephrine administration by intramuscular or subcutaneous injection, or by inhalation, with intravenous epinephrine and intramuscular saline as the positive and negative controls, respectively. Maximum plasma epinephrine concentrations were higher, and occurred more rapidly, after intramuscular injection than after subcutaneous injection or inhalation, and were 7719+/-3943 (S.E.M.) pg/mL at 32.5+/-6.6 min, 2692+/-863 pg/mL at 111.7+/-30.8 min and 1196+/-369 pg/mL at 45. 8+/-19.2 min, respectively. Intravenous injection of epinephrine resulted in a plasma concentration of 3544+/-422 pg/mL at 5 min, and an elimination half-life (t(1/2)) of 11.0+/-2.5 min. In the saline control study, the endogenous epinephrine concentration peaked at 518+/-142 pg/mL. CONCLUSION: In this model, absorption of epinephrine was significantly faster after intramuscular injection than after subcutaneous injection or inhalation. The extent of absorption was satisfactory after both intramuscular and subcutaneous injections. Neither the rate nor the extent of absorption was satisfactory after administration by inhalation. [Gu X et al; Biopharm Drug Dispos 20 (8): 401-5 (1999). Available from, as of October 6, 2009:] PubMed Abstract
3 groups of 5 greyhounds received 1.5 ug/kg epinephrine 1:200,000 in either lidocaine 0.5%, bupivacaine 0.5% or 0.9% saline. Dogs were anesthetized and 40% of the allocated epinephrine solution was infiltrated beneath the perianal skin and each of the 4 quadrants of the rectal mucosa was injected with the remainder of the solution. Plasma epinephrine, lidocaine, bupivacaine, lactate, glucose and potassium concn were measured at 1, 2, 5, 10 and 30 min following infiltration. Peak plasma epinephrine concn were recorded 2 min following rectal mucosal infiltration in all 3 groups. Plasma epinephrine concn were significantly higher (p PubMed Abstract
Epinephrine is well absorbed after subcutaneous or IM injection; absorption can be hastened by massaging the injection site. Both rapid and prolonged absorption occur after subcutaneous injection of the longer-acting aqueous suspension (no longer commercially available in the US). Epinephrine also is absorbed following endotracheal administration, although serum concentrations achieved may be only 10% of those with an equivalent IV dose.. After oral inhalation of epinephrine in the usual dosage, absorption is slight and the effects of the drug are restricted mainly to the respiratory tract. Absorption increases somewhat when larger doses are inhaled, and systemic effects may occur.
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a structure estimation method(2), indicates that epinephrine is expected to have high mobility in soil(SRC). The pKa1 of epinephrine, a catecholamine(7), is 8.28(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because epinephrine partially exists as a cation and cations do not volatilize. Volatilization of the neutral species of epinephrine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-19 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Epinephrine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.4X10-8 mm Hg at 25 deg C(SRC), determined from a fragment constant method(6). Epinephrine deteriorates rapidly on exposure to air or light, turning red from oxidation to adrenochrome(7). Biodegradation data were not available(SRC, 2009); however, the compound was not affected by various strains of Mycobacterium(8).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a structure estimation method(2), indicates that epinephrine is not expected to adsorb to suspended solids and sediment(SRC). A pKa1 of 8.28(3) indicates epinephrine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3.162(SRC), from its log Kow of -2.59(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Epinephrine deteriorates rapidly on exposure to air or light, turning red from oxidation to adrenochrome(8). Biodegradation data were not available(SRC, 2009); however, the compound was not affected by various strains of Mycobacterium(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), epinephrine, which has an estimated vapor pressure of 7.4X10-8 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase epinephrine may be removed from the air by wet or dry deposition(SRC). Epinephrine deteriorates rapidly on exposure to air or light, turning red from oxidation to adrenochrome(3).