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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H49NO9
Molecular Weight 591.7328
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEVADINE

SMILES

[H][C@@]12CC[C@@]3([H])[C@]4(O)C[C@H](O)[C@@]5(O)[C@@]([H])(CN6C[C@@H](C)CC[C@@]6([H])[C@@]5(C)O)[C@]4(O)C[C@@]37O[C@]1(O)[C@H](CC[C@@]27C)OC(=O)C(\C)=C/C

InChI

InChIKey=DBUCFOVFALNEOO-HWBIYQLFSA-N
InChI=1S/C32H49NO9/c1-6-18(3)25(35)41-24-11-12-26(4)19-8-9-20-28(37)13-23(34)31(39)21(29(28,38)16-30(20,26)42-32(19,24)40)15-33-14-17(2)7-10-22(33)27(31,5)36/h6,17,19-24,34,36-40H,7-16H2,1-5H3/b18-6-/t17-,19-,20-,21-,22-,23-,24-,26-,27+,28+,29+,30+,31-,32-/m0/s1

HIDE SMILES / InChI

Molecular Formula C32H49NO9
Molecular Weight 591.7328
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 1
Optical Activity UNSPECIFIED

Cevadine, veratridine, and related lipophilic ceveratrum alkaloids cause activation of the voltage-sensitive Na+ channels of nerve, heart, and skeletal muscle cell membranes similar to pyrethrins. Both veratridine and cevadine alter the ion selectivity of Na+ channels and cause persistent activation. The receptor for these alkaloids has not been isolated, but experiments indicate it is distinct from that of pyrethrin. Structurally, veratridine and cevadine differ only in their acyl group. Cevadine has been used as an insecticide, acting as a paralytic agent with higher toxicity to insects than to mammals. It has been used to study Na+ channel blockers such as vincamine and vincanol by inducing Na+ channels in the presence and absence of the drugs being tested.

Approval Year

PubMed

PubMed

TitleDatePubMed
Neuroprotective action of a novel compound--M50463--in primary cultured neurons.
1999 Jan 2
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rats: veratrine (0.6 mg/kg, s.c.) significantly increased the plasma concentration of corticosterone, an endogenous biomarker for anxiety, compared to vehicle. https://www.ncbi.nlm.nih.gov/pubmed/26099814
Mouse:LD50 = 300mg/kg; oral Rat: LD50 = 980 mg/kg; oral
Route of Administration: Oral
In Vitro Use Guide
Cevadine sensitivity of sartorius muscles incubated in glutamate Ringer was about five times greater than that of muscles incubated in normal Ringer. Therefore, even 0.005 mmol/l cevadine could induce depolarization and membrane potential oscillations.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:10:32 GMT 2023
Edited
by admin
on Sat Dec 16 02:10:32 GMT 2023
Record UNII
ERQ7M6C50B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEVADINE
MI   WHO-DD  
Common Name English
CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-((2Z)-2-METHYL-2-BUTENOATE), (3.BETA.,4.ALPHA.,16.BETA.)-
Systematic Name English
VERATRINE
Common Name English
CEVANE-3.BETA.,4.BETA.,12,14,16.BETA.,17,20-HEPTOL, 4,9-EPOXY-, 3-(2-METHYLCROTONATE), (Z)-
Common Name English
Cevadine [WHO-DD]
Common Name English
NSC-93767
Code English
(3.BETA.,4.ALPHA.,16.BETA.)-4,9-EPOXYCEVANE-3,4,12,14,16,17,20-HEPTOL 3-((2Z)-2-METHYL-2-BUTENOATE)
Common Name English
CEVADINE [MI]
Common Name English
CEVADIN
Common Name English
CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-(2-METHYL-2-BUTENOATE), (3.BETA.(Z),4.ALPHA.,16.BETA.)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID4058237
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
WIKIPEDIA
Veratrine
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
NSC
93767
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
SMS_ID
100000128752
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-545-6
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
MERCK INDEX
m3302
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY Merck Index
FDA UNII
ERQ7M6C50B
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
PUBCHEM
5380394
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
EVMPD
SUB36232
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
CHEBI
28051
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
CAS
62-59-9
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
EVMPD
SUB13307MIG
Created by admin on Sat Dec 16 02:10:32 GMT 2023 , Edited by admin on Sat Dec 16 02:10:32 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY