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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
Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine.
2007 Dec 6
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
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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