CONIINE

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

Structure Search

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

HIDE SMILES / InChI

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
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20116429	Agonist 2678		10.2 µM [EC50]
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20116429	Agonist 2678		900.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesis of (S)-(+)-coniine.	2004 Oct 21	15490002
Enantioselective organocatalytic intramolecular aza-Michael reaction: a concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine.	2007 Dec 6	17985918
Asymmetric synthesis of 6-alkyl- and 6-arylpiperidin-2-ones. Enantioselective synthesis of (S)-(+)-coniine.	2007 Jun 21	17518477
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids.	2008 Aug 15	18642871
Stereoselective potencies and relative toxicities of coniine enantiomers.	2008 Oct	18763813
Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors.	2010 May-Jun	20116429
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	23086230

Patents

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 `Fri Dec 15 15:42:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:42:59 GMT 2023`
Record UNII	C479P32L2D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CONIINE

Common Name

English

CICUTINE

Common Name

English

CONIINE [HSDB]

Common Name

English

(S)-2-PROPYLPIPERIDINE

Systematic Name

English

CONICINE

Common Name

English

(2S)-2-PROPYLPIPERIDINE

Systematic Name

English

CONIINUM

Common Name

English

CONIINUM [HPUS]

Common Name

English

CONIINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C221