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Veratridine

HCID 6280
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
71-62-5
Standard 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
Molecular formula
C36H51NO11
Average molar mass
673.8 g/mol
Monoisotopic mass
673.34621144

Overview

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

Names & identifiers

Preferred name
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
English name
VERATRIDINE
Molecular formula
C36H51NO11
Molecular weight
673.79

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
1
Topological polar surface area
179 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
12
Rotatable bonds
5
Heavy atoms
48
Formal charge
0
Complexity
1,340

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
180 ℃ · 180℃
alpha
20 · D20 +8.0° (ethanol)
Boiling point
689.74 °C · 689.74°C (rough estimate)
Density
1.45 · 1.45±0.1 g/cm3 (20 ºC 760 Torr)
refractive index
1.663 · 1.6630 (estimate)
storage temp.
-20 °C · -20°C
solubility
50 mg/mL · ethanol: 50 mg/mL
form
powder
pka
9.54 · 9.54(at 25℃)
color
white to off-white
Merck
13 · 13,10016
BRN
78875 · 78875
Stability
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
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|
EWG's Food Scores
1 · 1
FDA UNII
4 BNP1KR7W · M4BNP1KR7W
EPA Substance Registry System
Veratridine (71-62-5)
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300+H310+H330-H315-H319-H335
Precautionary statements
260 · P260-P262-P280-P302+P352+P310-P304+P340+P310-P305+P351+P338
target organs
Nervous system, Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T+
Risk Statements
26 · 26/27/28-36/37/38-62-52/53-48/20
Safety Statements
26 · 26-36/37/39-45-61-36/37-28
RIDADR
1544 · UN 1544 6.1/PG 1
WGK Germany
2 · 2
RTECS
5600000 · YX5600000
F
10 · 10
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
1 DermalAcute · Acute Tox. 1 DermalAcute Tox. 1 InhalationAcute Tox. 1 OralAquatic Chronic 3Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2 InhalationSTOT SE 3
Hazardous Substances Data
71 · 71-62-5(Hazardous Substances Data)
Toxicity
50 in · LD50 in mice (mg/kg): 1.35 i.p. (Swiss, Bauer); 0.42 i.v. (Krayer); 6.3 s.c. (Tanaka)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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.

Hazard information

Fire PotentialSLIGHT.
Hazards Summary · 1 item

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 · 3 items

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%)

Toxicology

Interactions · 1 item

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 · 1 item

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 · 4 items

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.

Safety data

F
10
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
2
rtecs
YX5600000
ridadr
UN 1544 6.1/PG 1
Toxicity
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
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T+
safety_code
26-36/37/39-45-61-36/37-28
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
target organs
Nervous system, Respiratory system
Hazard statements
H300+H310+H330-H315-H319-H335
Hazard Classifications
Acute Tox. 1 DermalAcute Tox. 1 InhalationAcute Tox. 1 OralAquatic Chronic 3Eye Irrit. 2Repr. 2Skin Irrit. 2STOT RE 2 InhalationSTOT SE 3
Precautionary statements
P260-P262-P280-P302+P352+P310-P304+P340+P310-P305+P351+P338
Hazardous Substances Data
71-62-5(Hazardous Substances Data)

Chemistry & industry

Pharmacology

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.

Uses & manufacturing

Uses · 3 items

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 · 1 item

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)
Applications · 3 items

DescriptionThis 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.

UsesVeratridine 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.

General DescriptionVeratridine 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.

Suppliers61 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海相辉医药科技有限公司13761987713; 13761987713 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
Ascent Scientific4401179829988 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
河南久化生物科技有限公司15738884691 153248764872949584887 237654463 · [email protected]
上海如吉生物科技发展有限公司021-69955236-807 13918189704 · [email protected]
上海跃腾生物技术有限公司021-36031160 13311776681 · [email protected]
陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
成都埃法生物科技有限公司028-85142057, 18030712385 · [email protected]
济南药研药物化学有限公司[email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
成都格利普生物科技有限公司028-87075086 13350802083 · [email protected]
南京美韬医药科技有限公司[email protected] · [email protected]
Aladdin Scientific[email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
上海贝万塔生物科技有限公司021-67187366 19901745723 · [email protected]
上海莫奇生物科技有限公司13341702378 · [email protected]
湖北萃园生物科技有限公司18162795156 18162795156 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海同田生物技术有限公司021-51320588 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]

Additional notes

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

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes