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Epinephrin Produkt Beschreibung

L(-)-Epinephrine Struktur
Englisch Name:

Epinephrin Eigenschaften

215 °C (dec.)(lit.)
-51.5 º (c=4, 1M HCl, dry sub)
316.88°C (rough estimate)
1.1967 (rough estimate)
-51.5 ° (C=4, 1mol/L HCl)
storage temp. 
Practically insoluble in water, in ethanol (96 per cent) and in methylene chloride. It dissolves in hydrochloric acid.
8.66(at 25℃)
Fine Crystalline Powder
White to light beige
<0.01 g/100 mL at 18 ºC
Air & Light Sensitive
> 212°C
Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Light sensitive.
CAS Datenbank
51-43-4(CAS DataBase Reference)
NIST chemische Informationen
EPA chemische Informationen
Epinephrine (51-43-4)
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T
R-Sätze: 23/24/25-52/53-36/37/38-33
S-Sätze: 36/37/39-45-61-26-23
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS-Nr. DO2625000
HazardClass  6.1
PackingGroup  II
HS Code  29373100
Giftige Stoffe Daten 51-43-4(Hazardous Substances Data)
Toxizität LD50 i.p. in mice: 4 mg/kg (Lands)
Bildanzeige (GHS)
Alarmwort Achtung
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H300 Lebensgefahr bei Verschlucken. Akute Toxizität oral Kategorie 2 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H310 Lebensgefahr bei Hautkontakt. Acute toxicity,dermal Category 1, 2 Achtung P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 Lebensgefahr bei Einatmen. Akute Toxizität inhalativ Kategorie 1 Achtung P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
P261 Einatmen von Staub vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P320 Besondere Behandlung dringend erforderlich
P330 Mund ausspülen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P405 Unter Verschluss aufbewahren.
P403+P233 An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.

Epinephrin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R33:Gefahr kumulativer Wirkungen.

S-Sätze Betriebsanweisung:

S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).


The combination of the catechol nucleus, the β-hydroxyl group, and the N-methyl give EPI a direct action and a strong affinity for all adrenergic receptors. Epinephrine and all other catechols are chemically susceptible to oxygen and other oxidizing agents, especially in the presence of bases and light, quickly decomposing to inactive quinones. Therefore, all catechol drugs are stabilized with antioxidants and dispensed in air-tight amber containers.

Chemische Eigenschaften

off-white powder




Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.


L-Adrenaline (Epinephrine) belongs to a group of the compounds known as catecholamines, which play an important role in the regulation of physiological process in living organisms. The antioxidant activity and antioxidant mechanism of L-adrenaline was cla


Gibberellic Acid-3 (GA-3) is a plant growth regulator


ChEBI: The R-enantiomer of adrenaline. It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response.

Vorbereitung Methode

Epinephrine is synthesized in the body from the nonessential amino acid tyrosine. Tyrosineundergoes hydroxylation to produce DOPA (3,4-dihydroxyphenylalanine). DOPA decarboxylationproduces dopamine, which is hydroxylated to norepinephrine. Norepinephrine, whichis closely related to epinephrine, performs a number of similar functions in the body. The prefix “nor” associated with a compound is used to denote an alkylated nitrogen in the compoundthat has lost an alkyl group. It comes from the German N-ohne-radical, which means Nitrogenwithout the radical. Therefore norepinephrine is epinephrine minus the methyl, CH3, radicalon the nitrogen. The methylation of norepinephrine gives epinephrine.


Epinephrine administered subcutaneously is used to manage severe acute episodes of bronchospasm and status asthmaticus. In addition to its bronchodilator activity through β-adrenoceptor stimulation, a portion of the therapeutic utility of epinephrine in these acute settings may be due to a reduction in pulmonary edema as a result of pulmonary vasoconstriction, the latter effect resulting from α-adrenoceptor stimulation.

Manufacturing Process

1 part by weight of ω-chloro-3,4-dihydroxyacteophenone in 1 part by weight of ethanol was heated with 60% aqueous solution of methylamine. The crystal of 3,4-dihydroxy-ω-methylaminoacteophenone obtained was transformed in hydrochloride by action of diluted hydrochloric acid. The base of (-)-3,4- dihydroxy-ω-methylaminoacteophenone was prepared by addition of ammonium hydroxide solution.


Bronkaid (Bayer); Epipen (Meridian); Primatene (Wyeth); Sus-Phrine (Forest); Twinject (Verus);Adrefil;Adrehinal;Adrenalin medihal;Adrenalina ace.p.d.;Adrenalina clorhi;Adrenalina delta;Adrenalina fustery;Adrenalina hormona;Adrenalina p davis;Adrenalina wiener;Bronkaid mistometer;Cetanest;D epinefrin;Dento-caine;Depinefrin;Dysne-inhal;E-caprine;Epiboran ofteno;Epinephrine pediatric;Epineramine;Glaucadrine;Glaucoaicon;Glauconin;Glaucotahil;Isopto epinefrina;Levoreninl-adrenaline;Licothionil;Lidoacton;Lyodrin;Marcaom;Methylaminoethanolcatechol;Neo-rybarex;Niphridine;Orostat;P2e1;Paranephrine;Piladren;Sedo-asmol;Suprarenine;Suprexon 5;Susphrine;Vaponephrine;Xylestesin a.

Therapeutic Function


Weltgesundheitsorganisation (WHO)

Epinephrine, first isolated in 1899, is the main hormone secreted by the adrenal medulla. It is widely used as a vasoconstrictor substance and in the treatment of anaphylactic shock. Its use in combination with local anaesthetics to prolong infiltration anaesthesia has been associated with systemic reactions including serious cardiovascular and cerebrovascular incidents. Regulations restricting the concentrations permitted in such preparations have been introduced in many countries but combination products containing epinephrine or levarterenol in concentrations of 1:80,000 or less remain widely available. Representative preparations are included in the WHO Model List of Essential Drugs. (Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert Committee, 722, , 1985)

Biologische Funktion

Epinephrine is found only in very low concentrations in the mammalian CNS, and it is unlikely to play a major role as a neurotransmitter.

Allgemeine Beschreibung

Epinephrine (E, Adrenalin) differs from NE only bythe addition of an N-methyl group. Like the other CAs, E islight sensitive and easily oxidized on exposure to air becauseof the catechol ring system. The development of apink-to-brown color indicates oxidative breakdown. Tominimize oxidation, solutions of the drug are stabilized bythe addition of reducing agents such as sodium bisulfite. Eis also destroyed readily in alkaline solutions and by metals(e.g., Cu, Fe, Zn) and weak oxidizing agents. It is used inaqueous solution for inhalation as the free amine. Like otheramines, it forms salts with acids, hydrochloride, and thebitartrate being the most common.
Like NE, it lacks oral activity and has short DOA.However, it is much more widely used clinically than NE.E is a potent stimulant of all α1-,α2-,β1-,β2-, and β3-adrenoceptors, and thus it switches on all possible adrenergicreceptors, leading to a whole range of desired and sideeffects. Particularly prominent are the actions on the heartand on vascular and other smooth muscle. It is a very potentvasoconstrictor and cardiac stimulant. NE has, in general,greater β-activity caused by an additional N-methyl group.Therefore, E is used to stimulate the heart in cardiac arrest.Although intravenous infusion of E has pronounced effectson the cardiovascular system, its use in the treatment ofheart block or circulatory collapse is limited because of itstendency to induce cardiac arrhythmias.

Allgemeine Beschreibung

White to nearly-white microcrystalline powder or granules. Odorless. Melting point 211-212°C. Aqueous solutions are slightly alkaline. Slightly bitter, numbing taste.

Air & Water Reaktionen

L(-)-Epinephrine darkens slowly on exposure to air and light. Water insoluble. Readily soluble in aqueous solutions of inorganic acids. Solutions undergo oxidation in the presence of oxygen.

Reaktivität anzeigen

L(-)-Epinephrine is incompatible with oxidizers, alkalis, copper, iron, silver, zinc and other metals; gum and tannin. L(-)-Epinephrine is also incompatible with acids, acid chlorides and acid anhydrides. L(-)-Epinephrine reacts with salts of sulfurous acid .


Flash point data for L(-)-Epinephrine are not available. L(-)-Epinephrine is probably combustible.

Mechanism of action

The effects on pulmonary function are quite rapid, with peak effects occurring within 5 to 15 minutes. Measurable improvement in pulmonary function is maintained for up to 4 hours.The characteristic cardiovascular effects seen at therapeutic doses of epinephrine include increased heart rate, increased cardiac output, increased stroke volume, an elevation of systolic pressure and decrease in diastolic pressure, and a decrease in systemic vascular resistance. The cardiovascular response to epinephrine represents the algebraic sum of both α- and β-adrenoceptor stimulation. A decrease in diastolic blood pressure and a decrease in systemic vascular resistance are reflections of vasodilation, a β2-adrenoceptor response. The increase in heart rate and systolic pressure is the result of either a direct effect of epinephrine on the myocardium, primarily a β1 effect, or a reflex action provoked by a decrease in peripheral resistance, mean arterial pressure, or both. Overt α-adrenoceptor effects, such as systemic vasoconstriction, are not obvious unless large doses are used.

Clinical Use

The ability of epinephrine to stimulate β2-receptors hasled to its use by injection and by inhalation to relaxbronchial smooth muscle in asthma and in anaphylacticreactions. Several OTC preparations (e.g., Primatene, Bronkaid)used for treating bronchial asthma use E. It is also usedin inhibiting uterine contraction. Because of its α-activity, Eis used to treat hypotensive crises and nasal congestion, toenhance the activity of local anesthetics, and as a constrictorin hemorrhage.
In addition, E is used in the treatment of open-angle glaucoma,where it apparently reduces intraocular pressure byincreasing the rate of outflow of aqueous humor from theanterior chamber of the eye. The irritation often experiencedon instillation of E into the eye has led to the developmentof other preparations of the drug that potentially are not asirritating. One such example is dipivefrin.

Clinical Use

Epinephrine is used in a variety of clinical situations, and although concern has been expressed about the use of epinephrine in asthma, it is still used extensively for the management of acute attacks.


Patients treated with recommended dosages of epinephrine will complain of feeling nervous or anxious. Some will have tremor of the hand or upper extremity and many will complain of palpitations. Epinephrine is dangerous if recommended dosages are exceeded or if the drug is used in patients with coronary artery disease, arrhythmias, or hypertension. The inappropriate use of epinephrine has resulted in extreme hypertension and cerebrovascular accidents, pulmonary edema, angina, and ventricular arrhythmias, including ventricular fibrillation. At recommended dosages, adverse effects from inhaled isoproterenol are infrequent and not serious. When excessive dosages are used, tachycardia, dizziness, and nervousness may occur, and some patients may have arrhythmias.


Human poison by subcutaneous route. Experimental poison by ingestion, skin contact, subcutaneous, intraperitoneal, intravenous, and intramuscular routes. Human systemic effects: cardiomyopathy includmg infarction, arrhythmias. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as an adrenergic, sympathomimetic, vasoconstrictor, bronchodilator, and cardiac stimulant.

Chemical Synthesis

Epinephrine, L-1-(3,4-dihydroxyphenyl)-2-methylaminoethanol (11.1.2), is obtained from the adrenal glands tissue of livestock [1,2] as well as in a synthetic manner. Epinephrine is synthesized from ω-chloro-3,4-dihydroxyacetophenone—chloroacetylpyrocatechine—the reaction of which with excess of methylamine gives ω-methylamino-3,4- dihydroxyacetophenone (11.1.1). Reduction of this using hydrogen over Raney nickel, or action of aluminum amalgam, or electrolytic reduction gives D,L-epinephrine (11.1.2) [3–9], which is separated into isomers using (+) tartaric acid .

Veterinary Drugs and Treatments

Epinephrine is employed primarily in veterinary medicine as a treatment for anaphylaxis or cardiac resuscitation. Because of its vasoconstrictive properties, epinephrine is added to local anesthetics to retard systemic absorption and prolong effect.


Epinephrine is ultimately metabolized by COMT and MAO to 3-methoxy-4-hydroxy-mandelic acid (vanillylmandelic acid), which is excreted as the sulfate or glucuronide in the urine. Only a very small amount is excreted unchanged.

läuterung methode

L-Adrenaline has been recrystallised from EtOH/AcOH/NH3 [Jensen J Am Chem Soc 57 1765 1935]. Itis sparingly soluble in H2O, readily in acidic or basic solutions but insoluble in aqueous NH3, alkali carbonate solutions, EtOH, CHCl3, Et2O or Me2CO. It has also been purified by dissolving in dilute aqueous acid, then precipitating it by adding dilute aqueous ammonia or alkali carbonates. It is readily oxidised in air and turns brown on exposure to light and air. (Epinephrine readily oxidises in neutral alkaline solution. This can be diminished if a little sulfite is added). Store it in the dark under N2. [Lewis Br J Pharmacol Chemother 9 488 1954]. The hydrogen oxalate salt has m 191-192o(dec, evacuated capillary) after recrystallisation from H2O or EtOH [Pickholz J Chem Soc 928 1945]. [Beilstein 13 H 830, 13 III/IV 2927.]

Toxicity evaluation

Epinephrine is available in nebulized racemic dosage form for inhalation.Intoxication from catecholamine usually results from iatrogenic overdoses, accidental intravenous administration, and the injection of solution intended for nebulization. High concentrations of dopamine present inside of a cell than there are vesicles to store it in, oxidative stress can occur and cause damage or death to the cell. It is thought that dopamine overload causes biochemical damage to cellular mitochondria, that provide the cell with all of the energy it requires to function, resulting in death of the cell. Catecholamines produced circulatory changes that reversed propofol anesthesia in animal models.

Epinephrin Upstream-Materialien And Downstream Produkte


Downstream Produkte

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