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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
Structure of CONIINE HYDROBROMIDE

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

HIDE SMILES / InChI
Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

Description
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.

Originator

Gieseke, L.
3
Curator's Comment: Originator for (+)-coniine is unknown. 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.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 10.2 µM [EC50]
Agonist
2678
 900.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

20030224033
7
20050038451
5
20050203190
8
20060089525
5
20070021649
3
20070032695
3
20070055095
3
20080081945
3
20080097349
3

Sample Use Guides

In Vivo Use Guide
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
The EC50 values of (+)-coniine HCl was 45 uM at eliciting changes in membrane potential in the human rhabdomyosarcoma cell line TE-671
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:51:14 GMT 2023
Edited
by admin
on Sat Dec 16 14:51:14 GMT 2023
Record UNII
92KKC0S28T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONIINE HYDROBROMIDE
MI  
Common Name English
CONIINE HBR
Common Name English
(2S)-2-PROPYLPIPERIDINE HBR
Common Name English
CONIINUM BROMATUM
HPUS  
Common Name English
CONIINUM BROMATUM [HPUS]
Common Name English
CONIINE HYDROBROMIDE [MI]
Common Name English
CICUTINE HBR
Common Name English
CONICINE HBR
Common Name English
(2S)-2-PROPYLPIPERIDINE HYDROBROMIDE
Systematic Name English
CONICINE HYDROBROMIDE
Common Name English
CICUTINE HYDROBROMIDE
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
PUBCHEM
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
FDA UNII
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
EPA CompTox
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
ECHA (EC/EINECS)
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
NCI_THESAURUS
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
MERCK INDEX
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
CAS
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
Related Record Type Details
Structure of CONIINE
PARENT -> SALT/SOLVATE
NIH
NCATS
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