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아트로핀

아트로핀
아트로핀 구조식 이미지
카스 번호:
51-55-8
한글명:
아트로핀
동의어(한글):
아트로핀;아트로핀,그염류및유도체
상품명:
Atropine
동의어(영문):
Atropin;ATROPINE;Atropina;Eyesules;Atropinol;Atropisol;HYOSCYAMINE;DL-ATROPINE;t-3-ylester;Atropine,99%
CBNumber:
CB2163178
분자식:
C17H23NO3
포뮬러 무게:
289.37
MOL 파일:
51-55-8.mol

아트로핀 속성

녹는점
115-118 °C
끓는 점
431.53°C (rough estimate)
밀도
1.0470 (rough estimate)
굴절률
1.5200 (estimate)
인화점
2℃
저장 조건
-20°C
용해도
H2O: 2 mg/mL
물리적 상태
powder
산도 계수 (pKa)
9.7(at 21℃)
색상
white
수용성
1.6g/L(18 ºC)
감도
Light Sensitive
Merck
14,875
BRN
91260
InChIKey
RKUNBYITZUJHSG-SPUOUPEWSA-N
CAS 데이터베이스
51-55-8(CAS DataBase Reference)
NIST
Atropine(51-55-8)
EPA
Atropine (51-55-8)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T+,Xn,F
위험 카페고리 넘버 26/28-36/37/38-20/21/22-36-11
안전지침서 25-45-36-26-36/37-16
유엔번호(UN No.) 1544
WGK 독일 3
RTECS 번호 CK0700000
F 고인화성물질 8-10-23
TSCA Yes
위험 등급 6.1
포장분류 III
HS 번호 29399900
유해 물질 데이터 51-55-8(Hazardous Substances Data)
독성 LD50 orally in rats: 750 mg/kg (Cahen, Tvede)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H300 삼키면 치명적임 급성 독성 물질 - 경구 구분 1,2 위험 P264, P270, P301+P310, P321, P330,P405, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H330 흡입하면 치명적임 급성 독성 물질 흡입 구분 1, 2 위험 P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P284 호흡 보호구를 착용하시오.
P310 즉시 의료기관(의사)의 진찰을 받으시오. 삼켰다면 즉시 의료기관(의사)의 도움을 받으시오.
P311 의료기관(의사)의 진찰을 받으시오.
P320 긴급히 (…) 처치를 하시오.
P330 입을 씻어내시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

아트로핀 C화학적 특성, 용도, 생산

개요

Atropine is considered to be the most effective antidote for both OP and CB intoxication. By effectively competing with acetylcholine for the same cellular receptors, it prevents overstimulation of the autonomous parasympathetic system. Most importantly, it helps prevent asphixia, the main cause of death. In human subjects, it is customary to constantly infuse atropine in order to maintain optimal concentration throughout recovery from the “cholinergic crisis.” In wildlife rehabilitation, this is impractical and subjects need to be repeatedly injected with atropine.

개요

Atropine is a naturally occurring tropane alkaloid extracted from plants of the family Solanaceae including deadly nightshade (A. belladonna). It is a non-selective, competitive antagonist of the muscarinic acetylcholine receptor types M1, M2, M3, M4, and M5 (pKBs range from 8.9-9.8). Atropine increases firing of the sinoatrial node and conduction through the atrioventricular node of the heart, opposes the actions of the vagus nerve, blocks acetylcholine receptor sites, and decreases bronchial secretions. It is classified as an anticholinergic (parasympatholytic) drug and commonly used to dilate the pupils, increase heart rate, reduce salivation and other secretions, and as an antidote against organophosphate poisoning.

화학적 성질

Atropine, also known as daturine, C17H23NO3, white, crystalline substance, optically inactive, but usually contains levorotatory hyoscyamine. Compound is soluble in alcohol, ether, chloroform, and glycerol; slightly soluble in water.

화학적 성질

White or almost white, crystalline powder or colourless crystals.

물리적 성질

Appearance: atropine appears as colourless, odourless crystals or a white crystalline powder. Solubility: very soluble in water and soluble in ethanol. Melting point: melting point of atropine isn’t higher than 189?°C (melting time decomposition) (Chinese Pharmacopoeia), 114–118?°C (United States Pharmacopeia) and 115– 119?°C (British Pharmacopoeia). The chemical structure of atropine is made up of amino alcohol esters. It is easy for atropine to be hydrolysed into tropine and despun tropic acid under alkaline condition. Atropine is stable in faintly acid and neutral aqueous solution, most stable at pH 3.5–4.0.

Originator

Atromed,Promed Exports,India

역사

Mandragora (mandrake) was described for treatment of wounds, gout and sleeplessness and as a love potion in the fourth century BC by Theophrastus. Atropine extracted from the Egyptian henbane was used by Cleopatra in the last century BC to dilate her pupils in the hope that she would appear more alluring. In the Renaissance, women used the juice of the berries of Atropa belladonna to enlarge the pupils of their eyes for cosmetic reasons. It isn’t until the first century AD that Dioscorides found that wine containing mandrake can be used as an anaesthetic treatment for pain or sleeplessness in surgery or cautery. The combination of extracts containing tropane alkaloids and opium was used to treat diseases, which was popular in the Roman and Islamic Empires and Europe. The combination was replaced by the use of ether, chloroform and other modern anaesthetics about 100?years ago. The mydriatic effects of atropine were studied by the German chemist Friedlieb Ferdinand Runge (1795–1867). In 1831, the German pharmacist Heinrich F.? G. Mein (1799–1864) succeeded in separating pure atropine from plants. The substance was first synthesized by German chemist Richard Willst?tter in 1901. In 1889, Richard Willst?tter first confirmed the chemical structure of atropine. Atropine was first synthesized by A.?Ladenburg. Homatropine, a kind of tropic alkaline ester, is used in the diagnosis and treatment in ophthalmology, and it has a shorter acting time than atropine. Quaternary ammonium compounds of atropine obtained by alkylation of nitrogen atoms have anticonvulsant function, which does not affect the central nervous system, due to their polarity. In 1970, atropine sulphate was synthesized in Hangzhou, the location of the first pharmaceutical factory in China, which increased the yield, reduced the cost and met the requirements of clinics.

용도

anticholinergic, mydriatic

용도

Atropine is used in medicine and is an antidote for cholinesteraseinhibiting compounds, such as organophosphorus insecticides and certain nerve gases. Atropine is commonly offered as the sulfate. Atropine is used in connection with the treatment of disturbances of cardiac rhythm and conductance, notably in the therapy of sinus bradycardia and sick sinus syndrome. Atropine is also used in some cases of heart block. In particularly high doses, atropine may induce ventricular tachycardia in an ischemic myocardium. Atropine is frequently one of several components in brand name prescription drugs.

용도

Scopolamine is found in the leaves of Daturametel L., D. meteloides L., and D. fastuosavar. alba (Cordell 1978). It is used as asedative, a preanesthetic agent, and in thetreatment of motion sickness (Merck 1989).

생산 방법

Atropine is prepared by extraction from Datura stramonium, or synthesized. The compound is toxic and allergenic.

정의

An alkaloid that is the 3(s)-endo isomer of atropine.

정의

atropine: A poisonous crystalline alkaloid,C17H23NO3; m.p. 118–119°C. Itcan be extracted from deadly nightshadeand other solanaceous plantsand is used in medicine to treat colic,to reduce secretions, and to dilatethe pupil of the eye.

Indications

This product was recorded in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the Indian Pharmacopoeia (2010), the European Pharmacopoeia (9.0th ed.), the International Pharmacopoeia (5th ed.) and the Korean Pharmacopoeia (10th ed.). Atropine sulphate is commonly used in clinics. Dosage forms are injection, tablet and eye ointment; atropine sulphate was mainly used to treat toxic shock and organic phosphorus pesticide poisoning, to relieve visceral colic, as preanaesthetic medication and to reduce bronchial mucus secretion. The indications of atropine sulphate eye gel are iridocyclitis, fundus examination and mydriasis.

Manufacturing Process

Atropin was obtained from belladonna roots and by racemisation of Lhyoscyamine with dilute alkali or by heating in chloroform solution. The alkaloid was crystallised from alcohol on addition of water, or from chloroform on addition of light petroleum, or from acetone in long prisms, m.p. 118°C, sublimed unchanged when heated rapidly. It is soluble in alcohol or chloroform, less soluble in ether or hot water, sparingly so in cold water (in 450 L at 25°C) and almost insoluble in light petroleum. Atropine is optically inactive.

상표명

Atrophate [Veterinary] (Schering-Plough Animal Health); Atropisol (Ciba Vision, US Ophthalmics); Isopto Atropine (Alcon).

Therapeutic Function

Anticholinergic

World Health Organization (WHO)

Atropine, an alkaloid with anticholinergic activity extracted from Atropa belladonna, has been widely used in medicines for centuries for its antispasmodic and mydriatic properties. It is also used for premedication prior to anaesthesia. Preparations containing atropine remain available and the substance is included in the WHO Model List of Essential Drugs.

일반 설명

Atropine is the tropine ester of racemictropic acid and is optically inactive. It possibly occurs naturallyin various Solanaceae, although some claim, with justification,that whatever atropine is isolated from naturalsources results from racemization of (-)-hyoscyamine duringthe isolation process. Conventional methods of alkaloidisolation are used to obtain a crude mixture of atropine andhyoscyamine from the plant material. This crude mixture isracemized to atropine by refluxing in chloroform or by treatmentwith cold dilute alkali. Because the racemizationprocess makes atropine, an official limit is set on thehyoscyamine content by restricting atropine to a maximumlevorotation under specified conditions.
Atropine occurs in the form of optically inactive, white,odorless crystals possessing a bitter taste. It is not very solublein water (1:460, 1:90 at 80°C) but is more soluble inalcohol (1:2, 1:1.2 at 60°C). It is soluble in glycerin (1:27),in chloroform (1:1), and in ether (1:25). Saturated aqueoussolutions are alkaline in reaction (pH 9.5). The free baseis useful when nonaqueous solutions are to be made, such asin oily vehicles and ointment bases. Atropine has a plasmahalf-life of about 2 to 3 hours. It is metabolized in the liverto several products, including tropic acid and tropine.

위험도

Extremely toxic, poison, paralyzes the parasympathetic nervous system by blocking the action of acetylcholine at nerve endings.

건강위험

The toxic effects are similar to atropine. Thesymptoms at toxic doses are dilation of the pupils, palpitation, blurred vision, irritation,confusion, distorted perceptions, hallucinations,and delirium. However, the mydriaticeffect is stronger than that of many othertropane alkaloids. Scopolamine is about threeand five times more active than hyocyamineand atropine, respectively, in causing dilationof the pupils. Its stimulating effect on thecentral nervous system, however, is weakerthan that of cocaine but greater than thatof atropine. The oral LD50 value in mice iswithin the range of 1200 mg/kg.
The histidine reversion–Ames test formutagenicity gave inconclusive results.

Pharmacology

Atropine is a blocker of typical M-choline receptor. In addition to terminating the gastrointestinal smooth muscle spasm, inhibiting glands, dilating pupils, increasing intraocular tension, adjusting vision through paralysis, accelerating heart rate and dilating bronchi, large doses of atropine dilate blood vessels, terminating the spasmodic contraction and improving minicirculation. Atropine can excite or inhibit the central nervous system in a dose-dependent manner. Atropine exerts longer and stronger effect on heart, intestine and bronchial smooth muscle than other belladonna alkaloids. Atropine also relaxes the pupillary sphincter and the ciliary muscle and dilates the pupils by blocking M-choline receptor in ocular tissue. Blockers of M-choline receptor included atropine, scopolamine, anisodamine and anisodine. Belladonnas not only block M-choline receptor in internal organ cells but also in the central nervous system. Compared with atropine, scopolamine has an oxygen bridge, which increases central nervous system function. The oxygen bridge of scopolamine is partially broken and then becomes anisodamine, which is difficult to pass through the blood-brain barrier, and symptoms caused by atropine in the central nervous system were less than that caused by atropine. Peak concentration of plasma can be reached at 15–20?min after intramuscular injection of atropine and at 1–2?h after oral administration and can last for 4–6?h. Most of the atropine can be absorbed by the gastrointestinal tract and other mucous membranes, and a little of the atropine can be absorbed by the eyes and skin. The t1/2 is 3.7–4.3?h. Binding rate of plasma protein is 14–22%. Volume of distribution is 1.7?L/kg after oral administration. Atropine can rapidly distribute to different organ systems and pass the blood-brain barrier and the placenta. After absorption by the eye’s conjunctiva, 30% of the products are excreted unchanged via the kidneys; the others become metabolites by hydrolysis and glucuronidation or glucosidation. After 1% gel eye drop, enlarged pupil function lasts for 7–10?days, and regulatory paralysis lasts for 7–12?days.

Clinical Use

The best known of the muscarinic blocking drugs are the belladonna alkaloids, atropine (Atropine) and scopolamine (Scopolamine).They are tertiary amines that contain an ester linkage. Atropine is a racemic mixture of DL-hyoscyamine, of which only the levorotatory isomer is pharmacologically active.Atropine and scopolamine are parent compounds for several semisynthetic derivatives, and some synthetic compounds with little structural similarity to the belladonna alkaloids are also in use.All of the antimuscarinic compounds are amino alcohol esters with a tertiary amine or quaternary ammonium group.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion and intramuscular routes: visual field changes, mydriasis @updlary dtlation), and muscle weakness. An experimental teratogen. Other experimental reproductive effects. An alkaloid. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Atropine, the D,L-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester of α-hydroxymethyl phenylacetic acid (14.1.4), can be synthesized by a standard scheme of synthesizing of tropane alkaloids. Condensation of maleyl aldehyde with methylamine and acetonedicarboxylic acid gives tropenone (14.1.1), which is the main starting material for the synthesis of both atropine and scopolamine. The carbonyl group of tropenone is reduced, thus forming tropenol (14.1.2), after which the double bond between C6 and C7 of the tropane ring is hydrogenated, giving tropine (14.1.3). Esterification of the tropenol gives the desired atropine (14.1.4) [1–6].

환경귀착

Atropine competitively antagonizes acetylcholine at the neuroreceptor site. Atropine prevents acetylcholine from exhibiting its usual action but does not decrease acetylcholine production. Cardiac muscle, smooth muscle, and the central nervous system are most affected by the antagonism of acetylcholine.

Purification Methods

Atropine crystallises from acetone or hot water, and sublimes at ~ 100o/high vacuum. [Beilstein 21/1 V 235.]

Toxicity evaluation

Free atropine is only slightly soluble in cold water. It melts at 115°C but decomposes upon boiling.
Environmental monitoring of atropine is not routinely performed by regulatory bodies. Hazardous short-term degradation products are not likely to occur. Accidental environmental exposure may occur through unintentional ingestion of toxic plants of the Solanaceae family, such as the deadly nightshade.

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