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Veratridine

HCID 6280
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
71-62-5
표준 SMILES
COc1ccc(C(=O)O[C@H]2CC[C@@]3(C)[C@@H]4CC[C@H]5[C@]6(O)C[C@H](O)[C@@]7(O)[C@@H](CN8C[C@@H](C)CC[C@H]8[C@@]7(C)O)[C@]6(O)C[C@@]53O[C@]24O)cc1OC
InChIKey
FVECELJHCSPHKY-YFUMOZOISA-N
분자식
C36H51NO11
평균 분자량
673.8 g/mol
단동위원소 질량
673.34621144

개요

Veratridine is a steroid. It has a role as a sodium channel modulator. It is functionally related to a cevane.

이름 및 식별자

우선 이름
Veratridine
IUPAC
[(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] 3,4-dimethoxybenzoate
영어명
VERATRIDINE
분자식
C36H51NO11
분자량
673.79

이름 및 동의어

veratridine71-62-53-VeratroylveracevineVeratrine (amorphous)M4BNP1KR7WCHEBI:28051Cevane-3,4,12,14,16,17,20-heptol, 4,9-epoxy-, 3-(3,4-dimethoxybenzoate), (3beta,4alpha,16beta)-4,9-Epoxycevane-3,4,12,14,16,17,20-heptol 3-(3,4-dimethoxybenzoate)4beta,12,14,16beta,17,20-hexahydroxy-4alpha,9-epoxycevan-3beta-yl 3,4-dimethoxybenzoateDTXSID2058467NSC-7524RefChem:901792
이름 더 보기
NSC 7524ybenzoate)VeratrdineVeratridine-RM,4alpha,16beta)-Veratridine, >=98%veratrine(amorphous)VERATRIDINE FREE BASE
DTXCID801768835(1R,10R,11S,12S,14R,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo(12.12.0.02,11.04,9.015,25.018,23.019,25)hexacosan-22-yl 3,4-dimethoxybenzoate200-758-4veratridin3-VeratroylveracevinNIOSH/FL5630000FL56300000[(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] 3,4-dimethoxybenzoate

데이터베이스 식별자

CAS
71-62-5
PubChem CID
6280
DTXSID
DTXSID2058467
ChEMBL
CHEMBL439496
ChEBI
CHEBI:28051
UNII
M4BNP1KR7W
EC Number
200-758-4
Nikkaji
J192.548B

물성

구조 계산 물성

XLogP
1
극성 표면적
179 Ų
수소 결합 공여자 수
6
수소 결합 수용자 수
12
회전 가능 결합 수
5
무거운 원자 수
48
형식 전하
0
복잡도
1,340

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Plant Toxins
Color/FormYELLOWISH-WHITE, AMORPHOUS POWDER
SolubilitySOL IN WATER; SLIGHTLY SOL IN ETHER
Melting Point180 °C
Optical RotationSPECIFIC OPTICAL ROTATION @ 20 °C/D (ETHANOL)= +8.0 DEG
Physical DescriptionYellowish-white solid; [Merck Index]
Other Experimental PropertiesRETAINS WATER TENACIOUSLY

물리화학적 성질

녹는점
180 ℃ · 180℃
끓는 점
689.74 °C · 689.74°C (rough estimate)
밀도
1.45 · 1.45±0.1 g/cm3 (20 ºC 760 Torr)
굴절률
1.663 · 1.6630 (estimate)
저장 조건
-20 °C · -20°C
용해도
50 mg/mL · 에탄올: 50mg/mL
물리적 상태
가루
산도 계수 (pKa)
9.54 · 9.54(at 25℃)
색상
흰색에서 황백색까지
Merck
13 · 13,10016
BRN
78875 · 78875
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 2개월 동안 보관할 수 있습니다.
InChIKey
FVECELJHCSPHKY-QYUNFSACNA-N
SMILES
[C@]123O[C@]4(O)C(OC(=O)C5=CC=C(OC)C(OC)=C5)CCC1(C)C4CCC2[C@]1([C@](O)(C2CN4C(CCC(C)C4)[C@](O)(C)[C@@]2(O)[C@@H](O)C1)C3)O |&1:0,2,26,27,38,41,43,r|
EPA
Veratridine (71-62-5)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H300+H310+H330 (42%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Fire PotentialSLIGHT.
Hazards Summary · 1건

Emergency treatment: Plants- veratrum alkaloids; Excessive amounts can cause death by central respiratory depression; [HSDB] Veratrum alkaloids (e.g., black snakeroot, false hellebore, and skunk cabbage) cause gastroenteritis, bradycardia, paresthesias, AV block, and syncope;; [Olson, p. 376-92] A strong irritant; May be fatal by all routes of exposure; May cause corrosive injuries to mucous membranes and upper respiratory tract; May cause disturbances to nervous system; A powerful muscle stimulant; Possible reproductive toxin; [Aldrich MSDS]

Special Reports · 3건

A REVIEW, WITH 37 REFERENCES, OF RELEASE OF CATECHOLAMINE BY VERATRIDINE & SCORPION VENOM & ALTERATIONS IN EXTRACELLULAR K & NA.[PATON DM; RELEASE INDUCED BY ALTERATIONS IN EXTRACELLULAR POTASSIUM AND SODIUM AND BY VERATRIDINE AND SCORPION VENOM; RELEASE CATECHOLAMINES ADRENERGIC NEURONS 323 (1979)]

REVIEW OF NEURONAL SODIUM CHANNEL REGULATION BY NEUROTOXINS, INCLUDING VERATRIDINE.[KRUEGER BK, BLAUSTEIN MP; REGULATION OF NEURONAL SODIUM CHANNELS BY NEURO TOXINS; SHAMOO, AD (ED) ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, VOL 358 2ND INTERNATIONAL CONFERENCE ON CARRIERS AND CHANNELS IN BIOLOGICAL SYSTEMS: TRANSPORT PROTEINS; NEW YORK, NY, USA FEB 4-6, 348 (1980)]

REVIEW OF NEUROTOXINS, INCLUDING VERATRIDINE, THAT ACT ON VOLTAGE SENSITIVE SODIUM CHANNELS IN EXCITABLE MEMBRANES.[CATTERALL NA; NEURO TOXINS THAT ACT ON VOLTAGE SENSITIVE SODIUM CHANNELS IN EXCITABLE MEMBRANES; GEROGE R, OKUN R (ED). ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY 20, 15 (1980)]

Hazard Classes and CategoriesAcute Tox. 1 (100%)

독성 정보

Interactions · 1건

THE ACTION OF VERATRIDINE ON THE RESTING MEMBRANE POTENTIAL OF INTACT CRAYFISH (PROCAMBARUS CLARKI) AXONS IN THE PRESENCE OF DIFFERENT EXTRACELLULAR ALKALINE-EARTH CATIONS WERE STUDIED USING INTRACELLULAR MICROELECTRODES. AT EXTRACELLULAR PH VALUES OF 7, 6, & 5, THE APPARENT BINDING SEQUENCE WAS CA2+ GREATER THAN OR EQUAL TO SR2+ MORE THAN MG2+ APPROX BA2+.

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 1건

Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by abolishing inactivation of sodium ion channels. It binds to intramembrane receptor site 2 and increases intracellular Ca2+ concentration. It acts by preferentially binding to activated Na+ channels causing persistent activation that leads to increased nerve excitability. (Wikipedia) The activation of the action potential Na+ ionophore by veratridine is time- and concentrationdependent and completely reversible. (A15424)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 4건

Eleven alkaloids obtained from Veratrum have been compared for their effects on the membrane potential and conductances of squid and crayfish giant axons. They can be classed in three groups. 1) Veratridine, cevadine and protoveratrines A and B cause the membrane to depolarize. The potency decreases in that order, and the concentrations of veratridine and cevadine required for 50% maximum depolarization are estimated to be 3.3 x 10-5 M and 3.7 x 10-3 M, respectively. The depolarization by veratridine is due primarily to a selective increase in resting sodium permeability of time membrane and is antagonized by tetrodotoxin. All of them are effective in augmenting and prolonging the negative (depolarizing) afterpotential. 2) Veratramin, eisorubijervine, muldaimine (5-veratranine 3-beta, 11-alpha-diol-11-acetate) and 5-veratranine-3alpha-11alpha-diol (1x10-4) re capable of blocking the action potential with little or no depolarization. 5-Veratranine-3-beta, 11-alpha-diol blocks both sodium and potassium conductance increases. 3) Cyclopamine, jervine, rubijervine and veratrosine have no effect on the resting and action potentials. Possible structure-activity relationships for these effects are discussed.

1X10-4 MOLAR VERATRIDINE APPLIED EXTERNALLY TO SQUID AXON CAUSED DEPOLARIZATION OF MEMBRANE. DURING INITIAL DEPOLARIZATION, REPETITIVE AFTERDISCHARGES INITIATED BY SINGLE STIMULUS SUBSIDED AS MEMBRANE FURTHER DEPOLARIZED & ACTION POTENTIAL BLOCKED. DEPOLARIZATION IS DUE PRIMARILY TO INCR IN RESTING SODIUM PERMEABILITY OF MEMBRANE.

VERATRIDINE CAUSED DEPOLARIZATION OF EXCITABLE CELLS & PRODUCED MARKED ELEVATION OF ADENOSINE 3',5'-MONOPHOSPHATE (CYCLIC AMP) & GUANOSINE 3',5'-MONOPHOSPHATE (CYCLIC GMP) LEVELS IN INCUBATED SLICES OF MOUSE CEREBRAL CORTEX.

SIGNS OF POISONING WITH VERATRINE AND RELATED ALKALOIDS ARE SALIVATION, PURGATION, VOMITING (EVEN IN THE COW), DIURESIS, EXCITABILITY FOLLOWED BY PROSTRATION, WEAK AND IRREGULAR PULSE, DEEP AND SLOW RESPIRATIONS, AND DEATH IN CONVULSIONS OR CONSEQUENTLY UPON PARALYSIS. THE LETHAL DOSE OF THE FRESH ROOT IS 1 G/KG IN THE HORSE AND 2 G/KG IN THE COW.

안전 데이터

wgk
2
rtecs
YX5600000
ridadr
UN 1544 6.1/PG 1
독성
LD50 in mice (mg/kg): 1.35 i.p. (Swiss, Bauer); 0.42 i.v. (Krayer); 6.3 s.c. (Tanaka)
risk_code
26/27/28-36/37/38-62-52/53-48/20
hazard_code
T+
safety_code
26-36/37/39-45-61-36/37-28
포장분류
II
위험 등급
6.1(a)
F 고인화성물질
10
Hazard Classifications
Acute Tox. 1 DermalAcute Tox. 1 InhalationAcute Tox. 1 OralAquatic Chronic 3Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2 InhalationSTOT SE 3
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
71-62-5(Hazardous Substances Data)

화학 및 산업

약리 정보

Mechanism of ActionTHE EFFECTS OF VERATRIDINE ON EXCITABLE TISSUES ARE PREDICTABLE, BASED ON ITS ABILITY TO ENHANCE SODIUM PERMEABILITY. EFFECTS INCLUDE, AMONG OTHERS, RELEASE OF NEUROTRANSMITTERS, HORMONES, DRUGS TAKEN UP BY NERVE ENDINGS, ETC.
Absorption, Distribution and ExcretionDATA GIVEN FOR LIPID SOLUBILITY, BINDING TO HUMAN ALBUMIN, & URINARY EXCRETION AFTER ORAL ADMIN TO HUMANS. STRUCTURE-ACTIVITY CORRELATIONS ARE DISCUSSED WITH RESPECT TO LIPID SOLUBILITY & PHARMACOLOGICAL PROPERTIES.

용도 및 제조

Uses · 3건

Isolated from seeds of Schoenocaulon officinale and the rhizome of Veratrum album; [Merck Index] A component of sabadilla (insecticide); [HSDB]

Farming (Pesticides) [Category: Industry]

Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by activating sodium ion channels.

Methods of Manufacturing · 1건

FROM SEED OF SCHOENOCAULON OFFICINALE (SCHLECHT & CHAM) A GRAY & ALSO FROM RHIZOME OF VERATRUM ALBUM L LILIACEAE. ...ISOLATED FROM COMMERCIAL VERATRINE AS SPARINGLY SOL NITRATE: BLOUNT, J CHEM SOC 1935, 122; VEJDELEK ET AL, CHEM LISTY 50, 603 (1956); COLL CZECH CHEM COMMUN 22, 98 (1957).

Formulations/PreparationsCOMPONENT OF SABADILLA (USED AS AN INSECTICIDE)
응용 분야 · 3건

개요This steroidal alkaloid from Veratrum viride was given this name by Bosetti. It is almost certainly identical with the amorphous veratrine isolated by Schmidt and Koppen, Merck, and Wright and Luff. The base is a colourless, amorphous powder which melts over a wide range. It has [α]22D + 8.0° (EtOH) and yields a sulphate nonahydrate which forms colourless silky needles that resinify in air. The nitrate is only sparingly soluble in H2O. The solution of the alkaloid in H2SO4 becomes orange-red and eventually crimson with a blue fluorescence while that in HCI is colourless. Alkaline hydrolysis furnishes veratric acid and cevine.

용도Veratridine causes Na+ channels to stay open during a sustained membrane depolarization by abolishing inactivation.This, in turn, opens voltage-activated calcium channels, thus increasing intracellular calcium content and inducing neurotransmitter release. Alkaloid neurotoxin which depolarizes excitable tissue; used to increase membrane sodium permeability.

일반 설명Veratridine is one of several alkaloids isolated from the seeds of Schoenocaulon officinale and from the rhizome of Veratrum album. The crude extract is called veratrine or sabadilla and contains cevadine, veratridine, cevadilline, sabadine and cevine. It is a neurotoxin, which belongs to the family Liliaceae and genus, Schoenocaulon. Veratridine is soluble in lipid.

공급사61 곳

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