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에핀에피린

에핀에피린
에핀에피린 구조식 이미지
카스 번호:
51-43-4
한글명:
에핀에피린
동의어(한글):
에피네프린;에핀에피린
상품명:
L(-)-Epinephrine
동의어(영문):
IOP;Adrin;Adrine;Bosmin;Suprel;Tonogen;Corisol;Epifrin;Vasoton;Adrenal
CBNumber:
CB8322199
분자식:
C9H13NO3
포뮬러 무게:
183.2
MOL 파일:
51-43-4.mol

에핀에피린 속성

녹는점
215 °C (dec.)(lit.)
알파
-51.5 º (c=4, 1M HCl, dry sub)
끓는 점
316.88°C (rough estimate)
밀도
1.1967 (rough estimate)
굴절률
-51.5 ° (C=4, 1mol/L HCl)
저장 조건
2-8°C
용해도
Practically insoluble in water, in ethanol (96 per cent) and in methylene chloride. It dissolves in hydrochloric acid.
산도 계수 (pKa)
8.66(at 25℃)
물리적 상태
Fine Crystalline Powder
색상
White to light beige
수용성
<0.01 g/100 mL at 18 ºC
감도
Air & Light Sensitive
분해온도
> 212°C
Merck
14,3619
BRN
2368277
안정성
Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Light sensitive.
CAS 데이터베이스
51-43-4(CAS DataBase Reference)
NIST
L-adrenaline(51-43-4)
EPA
Epinephrine (51-43-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T
위험 카페고리 넘버 23/24/25-52/53-36/37/38-33
안전지침서 36/37/39-45-61-26-23
유엔번호(UN No.) UN 2811 6.1/PG 2
WGK 독일 3
RTECS 번호 DO2625000
F 고인화성물질 8-10-23
TSCA Yes
위험 등급 6.1
포장분류 II
HS 번호 29373100
유해 물질 데이터 51-43-4(Hazardous Substances Data)
독성 LD50 i.p. in mice: 4 mg/kg (Lands)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H300 삼키면 치명적임 급성 독성 물질 - 경구 구분 1,2 위험 P264, P270, P301+P310, P321, P330,P405, P501
H310 피부와 접촉하면 치명적임 급성 독성 물질 - 경피 구분 1,2 위험 P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 흡입하면 치명적임 급성 독성 물질 흡입 구분 1, 2 위험 P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P310 즉시 의료기관(의사)의 진찰을 받으시오. 삼켰다면 즉시 의료기관(의사)의 도움을 받으시오.
P320 긴급히 (…) 처치를 하시오.
P330 입을 씻어내시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P302+P350 피부에 묻은 경우,비눗물로 부드럽게 씻기
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

에핀에피린 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

off-white powder

Originator

Adrenalin,Sopharma,Bulgaria

용도

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

용도

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

용도

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

정의

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

생산 방법

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.

Indications

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.

상표명

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

Vasoconstrictor

World Health Organization (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)

Biological Functions

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

일반 설명

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.

일반 설명

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

공기와 물의 반응

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.

반응 프로필

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 .

화재위험

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.

부작용

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.

Safety Profile

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 .
CB8322199.jpg

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.

신진 대사

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.

Purification Methods

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.

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