Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H17N |
| Molecular Weight | 127.2273 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC[C@H]1CCCCN1
InChI
InChIKey=NDNUANOUGZGEPO-QMMMGPOBSA-N
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m0/s1
| Molecular Formula | C8H17N |
| Molecular Weight | 127.2273 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesis of (S)-(+)-coniine. | 2004 Oct 21 |
|
| Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine. | 2007 Dec 6 |
|
| Asymmetric synthesis of 6-alkyl- and 6-arylpiperidin-2-ones. Enantioselective synthesis of (S)-(+)-coniine. | 2007 Jun 21 |
|
| 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
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:42:59 UTC 2023
by
admin
on
Fri Dec 15 15:42:59 UTC 2023
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| Record UNII |
C479P32L2D
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C221
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EPA PESTICIDE CODE |
70702
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207-282-6
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28322
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C479P32L2D
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1313334
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441072
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3474
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CONIINE
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m3759
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C479P32L2D
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C87476
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DTXSID8041795
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C007112
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458-88-8
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
