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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H49NO9.ClH
Molecular Weight 628.194
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEVADINE HYDROCHLORIDE

SMILES

Cl.[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=VSARLHXBMYVYSM-ZLVREPKBSA-N
InChI=1S/C32H49NO9.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 09:03:46 GMT 2023
Edited
by admin
on Sat Dec 16 09:03:46 GMT 2023
Record UNII
75GK03249U
Record Status Validated (UNII)
Record Version
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Name Type Language
CEVADINE HYDROCHLORIDE
Common Name English
CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-(2-METHYL-2-BUTENOATE), HYDROCHLORIDE, (3.BETA.(Z),4.ALPHA.,16.BETA.)-
Systematic Name English
CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-((2Z)-2-METHYL-2-BUTENOATE), HYDROCHLORIDE (1:1), (3.BETA.,4.ALPHA.,16.BETA.)-
Systematic Name English
CEVANE-3.BETA.,4.BETA.,12,14,16.BETA.,17,20-HEPTOL, 4,9-EPOXY-, 3-ANGELATE, HYDROCHLORIDE, (Z)-
Systematic Name English
Code System Code Type Description
FDA UNII
75GK03249U
Created by admin on Sat Dec 16 09:03:46 GMT 2023 , Edited by admin on Sat Dec 16 09:03:46 GMT 2023
PRIMARY
CAS
17666-25-0
Created by admin on Sat Dec 16 09:03:46 GMT 2023 , Edited by admin on Sat Dec 16 09:03:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID30657581
Created by admin on Sat Dec 16 09:03:46 GMT 2023 , Edited by admin on Sat Dec 16 09:03:46 GMT 2023
PRIMARY
PUBCHEM
16220094
Created by admin on Sat Dec 16 09:03:46 GMT 2023 , Edited by admin on Sat Dec 16 09:03:46 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY