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레세르핀

레세르핀
레세르핀 구조식 이미지
카스 번호:
50-55-5
한글명:
레세르핀
동의어(한글):
레세르핀
상품명:
Reserpine
동의어(영문):
H 520;R-e-s;Kitine;Rausan;reserp;Resine;rezide;Serpen;Anguil;Raucap
CBNumber:
CB4206679
분자식:
C33H40N2O9
포뮬러 무게:
608.68
MOL 파일:
50-55-5.mol

레세르핀 속성

녹는점
~265 °C (dec.)
알파
D23 -118° (CHCl3); D26 -164° (c = 0.96 in pyridine); D26 -168° (c = 0.624 in DMF)
끓는 점
655.12°C (rough estimate)
밀도
1.2336 (rough estimate)
굴절률
177 ° (C=1, DMF)
인화점
22℃
저장 조건
2-8°C
용해도
Practically insoluble in water, very slightly soluble in ethanol (96 per cent).
산도 계수 (pKa)
6.6(at 25℃)
물리적 상태
neat
optical activity
[α]20/D 123±3°, c = 1% in chloroform
수용성
Soluble in water.
Merck
14,8145
BRN
102014
안정성
Stable, but darkens slowly in light. Combustible. Incompatible with strong acids, reducing agents, oxidizing agents.
InChIKey
QEVHRUUCFGRFIF-MDEJGZGSSA-N
CAS 데이터베이스
50-55-5
NIST
Reserpine(50-55-5)
EPA
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5- trimethoxybenzoyl)oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha., 18.beta.,20.alpha.)-(50-55-5)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,Xi
위험 카페고리 넘버 22-67-36-10
안전지침서 22-36/37/39-26
유엔번호(UN No.) 3077
WGK 독일 3
RTECS 번호 ZG0350000
F 고인화성물질 10-23
TSCA Yes
포장분류 II
HS 번호 29399990
유해 물질 데이터 50-55-5(Hazardous Substances Data)
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
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
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P330 입을 씻어내시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

레세르핀 C화학적 특성, 용도, 생산

화학적 성질

off-white crystalline powder

화학적 성질

Reserpine is a white to pale buff to slightly yellow crystalline substance that darkens on exposure to light.

용도

Reserpine occurs in the roots of Rauwolfiaserpentina and other Rauwolfia species, suchas R. micrantha, R. canescens, and R. vomitoria Hook. It is used therapeutically as anantihypertensive agent and a tranquilizer. Itsuse has been reduced significantly because oftoxic side effects.

용도

An indole alkaloid found in Rauwolfia serpentina. Inhibits vesicular uptake of catecholamines and serotonin. Reserpine is reasonably anticipated to be a human carcinogen. Antihypertensive.

용도

An inhibitor of transport of biogenic amines into adrenal chromaffin granules

정의

ChEBI: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.

상표명

Rau-Sed (Bristol-Myers Squibb); Sandril (Lilly); Serpasil (Novartis).

Biological Functions

Reserpine (Serpasil) is the prototypical drug interfering with norepinephrine storage. Reserpine lowers blood pressure by reducing norepinephrine concentrations in the noradrenergic nerves in such a way that less norepinephrine is released during neuron activation. Reserpine does not interfere with the release process per se as does guanethidine.
Reserpine also interferes with the neuronal storage of a variety of central transmitter amines such that significant depletion of norepinephrine, dopamine, and 5- hydroxytryptamine (serotonin) occurs. This central transmitter depletion is responsible for the sedation and other CNS side effects associated with reserpine therapy. The depletion of brain amines also may contribute to the antihypertensive effects of reserpine.

일반 설명

Reserpine (Serpasil, Reserpoid, Rau-Sed, Sandril) is a white to light yellow, crystalline alkaloid,practically insoluble in water, obtained from various speciesof Rauwolfia. In common with other compounds with anindole nucleus, it is susceptible to decomposition by lightand oxidation, especially when in solution. In the dry state,discoloration occurs rapidly when reserpine is exposed tolight, but the loss in potency is usually small. In solution,reserpine may break down with no appreciable color changewhen exposed to light, especially in clear glass containers;thus, color change cannot be used as an index of the amountof decomposition.

일반 설명

Reserpine, a prototypicaland historically important drug, is an indole alkaloid obtainedfrom the root of Rauwolfia serpentina found in India.As is typical of many indole alkaloids, reserpine is susceptibleto decomposition by light and oxidation. Reserpine isextensively metabolized through hydrolysis of the esterfunction at position and yields methyl reserpate and3,4,5-trimethoxybenzoic acid. It not only depletes the vesiclestorage of NE in sympathetic neurons in PNS, neuronsof the CNS, and E in the adrenal medulla, but also depletesthe storage of serotonin and DA in their respective neuronsin the brain. Reserpine binds extremely tightly with andblocks VMAT that transports NE and other biogenic aminesfrom the cytoplasm into the storage vesicles. Thus in sympatheticneurons, NE, which normally is transported into thestorage vesicles, is instead metabolized by mitochondrialMAO in the cytoplasm. In addition, there is a gradual loss ofvesicle-stored NE as it is used up by release resulting fromsympathetic nerve activity so that the storage vesicles eventuallybecome dysfunctional. The end result is a depletion ofNE in the sympathetic neuron. Analogous effects are seen inthe adrenal medulla with E and with 5-HT in serotonergicneurons.

일반 설명

White or cream to slightly yellow crystals or crystalline powder. Odorless with a bitter taste.

공기와 물의 반응

Insoluble in water. Reacts slowly with air and water. Darkens slowly on exposure to light.

반응 프로필

Reserpine is a weak base and can form salts with strong acids. Incompatible with oxidizing agents and reducing agents.

위험도

Questionable carcinogen.

건강위험

Reserpine produces sedative, hypotensive,
LD50 value, intraperitoneal (mice): 5 mg/kg
LD50 value, oral (mice): 200 mg/kgand tranquilizing effects. This is due to itsactions of causing depletion of monoaminesfrom presynaptic nerve terminals in central and peripheral nervous systems. Theadverse side effects are drowsiness, nightmare, depression, excessive salivation, nausea, diarrhea, increased gastric secretion,abdominal cramps, and hypotension.

화재위험

Flash point data for Reserpine are not available; however, Reserpine is probably combustible.

생물학적 활성

Binds the vesicular monoamine transporter (VMAT2) and inhibits transport of biogenic amines into adrenal chromaffin granules and synaptic vesicles. Causes depletion of biogenic amine stores. Antihypertensive and antipsychotic.

Clinical Use

Reserpine is effective orally and parenterally for thetreatment of hypertension. After a single intravenous dose,the onset of antihypertensive action usually begins in about1 hour. After intramuscular injection, the maximumeffect occurs within approximately 4 hours and lasts about10 hours. When it is given orally, the maximum effectoccurs within about 2 weeks and may persist up to 4 weeksafter the final dose. When used in conjunction with otherhypotensive drugs in the treatment of severe hypertension,the daily dose varies from 100 to 250μg.

Clinical Use

When reserpine is given orally, its maximum effect is seenafter a couple of weeks. A sustained effect up to severalweeks is seen after the last dose has been given. This isbecause the tight binding of reserpine to storage vesicles continuesfor a prolonged time, and recovery of sympatheticfunction requires synthesis of new vesicles over a period ofdays to weeks after discontinuation of the drug. Most adverseeffects of reserpine (log P=4.37) are caused by CNS effectsbecause it readily enters the CNS. Sedation and inability toconcentrate or perform complex tasks are the most commonadverse effects. More serious is the occasional psychoticdepression that can lead to suicide, which support monoaminetheory of pathology of depression. Agents with fewer sideeffects have largely replaced reserpine in clinical use.

부작용

The most troublesome untoward effects of treatment with reserpine involve the CNS. Sedation and depression are the most common, although nightmares and thoughts of suicide also occur. Reserpine treatment, therefore, is contraindicated in patients with a history of severe depression. The occasional report of reserpine- induced extrapyramidal symptoms, which are similar to those seen in patients with Parkinson’ s disease, is believed to be a result of dopamine depletion from neurons in the CNS.
Peripheral nervous system side effects are the result of a reserpine-induced reduction of sympathetic function and unopposed parasympathetic activity; symptoms include nasal congestion, postural hypotension, diarrhea, bradycardia, increased gastric secretion, and occasionally impotence. Because of the increased gastric secretion, reserpine is contraindicated for patients with peptic ulcer. In patients with little cardiac reserve, reserpine must be administered with caution because of its ability to interfere with sympathetic stimulation of the heart.

Safety Profile

Confirmed human carcinogen producing tumors of the sh and brain. Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Mutation data reported. An experimental teratogen. Human and experimental reproductive effects by ingestion: sullbirth, reduced viability, and other neonatal measures or effects. In humans, 0.014 mg/kg causes psychotropic effects. A medicine with side effects. Used as an addltive permitted in the feed and drinking water of animals and/or for the treatment of food-producing animals. Also permitted in food for human consumption. A sedative. When heated to decomposition it emits toxic fumes of NOx.

잠재적 노출

Reserpine, a pharmaceutical, is a natu- rally occurring substance that is isolated from the roots of the plant rauwolfia serpentina. Insoluble in water. Reserpine is used as a hypertensive for humans and ani- mals; tranquilizer, and sedative. Permitted for use as an additive in food for human consumption, and the feed and drinking water of food-producing animals.

Carcinogenicity

Reserpine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

운송 방법

UN1544 Alkaloids, solid, n.o.s. or Alkaloid salts, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally haz- ardous substances, solid, n.o.s., Hazard class: 9; Labels: 9- Miscellaneous hazardous material, Technical Name Required.

Purification Methods

Crystallise reserpine from aqueous Me2CO or Et2O. [Woodward et al. Tertrahedron 2 155 1958, Beilstein 25 III/IV 1319.]

비 호환성

A weak acid; keep away from bases. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoa- cids, epoxides, and strong reducing agents such as hydri- deds and active metals. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithio- carbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases),thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur).

폐기물 처리

It is inappropriate and possi- bly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quanti- ties of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. 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. Consult with environmental regula- tory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/ mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

법규

Consumer Product Safety Commission (CPSC)
Any orally administered prescription drug for human use requires child-resistant packaging.
Environmental Protection Agency (EPA)
Comprehensive Environmental Response, Compensation, and Liability Act
Reportable quantity (RQ) = 5,000 lb.
Resource Conservation and Recovery Act
Listed Hazardous Waste: Waste code for which the listing is based wholly or partly on the presence of reserpine = U200.
Listed as a hazardous constituent of waste.
Food and Drug Administration (FDA)
Resperine is a prescription drug subject to labeling and other requirements.
All oral dosage drug products containing more than 1 mg of reserpine have been withdrawn from the market and may not be compounded, because such drug products were found to be unsafe or not effective.

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