Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H17N.BrH |
Molecular Weight | 208.139 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.CCC[C@H]1CCCCN1
InChI
InChIKey=BWMPAYPMHXMUAF-QRPNPIFTSA-N
InChI=1S/C8H17N.BrH/c1-2-5-8-6-3-4-7-9-8;/h8-9H,2-7H2,1H3;1H/t8-;/m0./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20116429Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18763813 | https://www.ncbi.nlm.nih.gov/pubmed/23086230 |
https://books.google.ru/books?id=FK2FCAAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false | http://casopisi.junis.ni.ac.rs/index.php/FUPhysChemTech/article/view/681
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20116429
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18763813 | https://www.ncbi.nlm.nih.gov/pubmed/23086230 |
https://books.google.ru/books?id=FK2FCAAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false | http://casopisi.junis.ni.ac.rs/index.php/FUPhysChemTech/article/view/681
Coniine is a neurotoxic piperidine alkaloid found in poison hemlock (Conium maculatum L.). Coniine which is considered to be racemic mixture first described by Gieseke in 1827; von Hoffman confirmed the structure in 1881; Ladenburg perfermed synthesis in 1886. Coniine enantiomers are nicotinic acetylcholine receptor (nAChR) agonists. The relative potencies of these enantiomers on TE-671 cells expressing human fetal nicotinic neuromuscular receptors had the rank order of (-)-coniine > (+/-)-coniine > (+)-coniine.
The rank order potency in SH-SY5Y cells which predominately express autonomic nAChRs was: (-)-coniine>(+)-coniine>
(+/-)-coniine.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20116429 |
10.2 µM [EC50] | ||
Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20116429 |
900.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids. | 2008 Aug 15 |
|
Stereoselective potencies and relative toxicities of coniine enantiomers. | 2008 Oct |
|
Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. | 2010 May-Jun |
|
Fetal muscle-type nicotinic acetylcholine receptor activation in TE-671 cells and inhibition of fetal movement in a day 40 pregnant goat model by optical isomers of the piperidine alkaloid coniine. | 2013 Jan |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18763813
The LD50 concentrations for coniine enantiomers in mice were 7.0 and 12.1 mg/kg i.v. for (–)- and (+)-coniine respectively
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23086230
The EC50 values of (+)-coniine HCl
was 45 uM at eliciting changes in membrane potential in the human rhabdomyosarcoma cell line TE-671
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C221
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
23617188
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | |||
|
92KKC0S28T
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | |||
|
DTXSID00980015
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | |||
|
211-286-3
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | |||
|
C87477
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | |||
|
m3759
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY | Merck Index | ||
|
637-49-0
Created by
admin on Sat Dec 16 14:51:14 GMT 2023 , Edited by admin on Sat Dec 16 14:51:14 GMT 2023
|
PRIMARY |
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD