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Details

Stereochemistry RACEMIC
Molecular Formula C8H17N
Molecular Weight 127.2273
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CONIINE, (±)-

SMILES

CCCC1CCCCN1

InChI

InChIKey=NDNUANOUGZGEPO-UHFFFAOYSA-N
InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3

HIDE SMILES / InChI

Molecular Formula C8H17N
Molecular Weight 127.2273
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9001585 https://www.ncbi.nlm.nih.gov/pubmed/27107833

Coniine is a toxic alkaloid contained in the seeds and leaves of Conium maculatum which is a well-known poisonous plant since ancient times. Coniine is a nicotinic acetylcholine receptor (nAChR) agonist. In vivo coniine causes a biphasic response of first stimulation followed by blockade of nicotinic receptors in the central nervous system and periphery. Clinical signs of poisoning include protrusion of the nictitating membrane, excessive salivation, and frequent urination and defecation, loss of coordination, muscle weakness, and tremors followed by collapse and death due to respiratory failure. Coniine is a documented teratogen in many domestic species.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 mM [EC50]
1100.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effects of coniine on peripheral and central synaptic transmission.
1966 May
Comparison of nicotinic receptor binding and biotransformation of coniine in the rat and chick.
1996 Dec 31
Stereoselective potencies and relative toxicities of coniine enantiomers.
2008 Oct
Antinociceptive activity of coniine in mice.
2009 Sep 7
The effect of coniine on presynaptic nicotinic receptors.
2016
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) LESS THAN 5 MG/KG
lethal dose < 5 mg/kg
Route of Administration: Oral
Anococcygeus muscles were first contracted by a submaximal concentration of phenylephrine (0.1 μM). When the contractile response had reached a plateau, nicotine (1–100 μM) was added to the medium. After the response to nicotine was complete and had subsided, tissues were washed several times until tensions returned to resting level. The nicotine-induced noradrenergic contraction response was examined in the presence of the NO-stimulated soluble guanylyl cyclase inhibitor ODQ (oxadiazolo quinoxaline-1-one; 10 μM) in anococcygeus muscle. In the presence of coniin (1–100 μM), a sequential contraction-relaxation procedure with phenylephrine and nicotine applied. Coniine inhibited the noradrenergic contraction response both in 10 and 100 μM concentration (–logIC50  =  4.57 ± 0.12 (M)).
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:02:45 GMT 2023
Edited
by admin
on Sat Dec 16 09:02:45 GMT 2023
Record UNII
04R53ZF48T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONIINE, (±)-
Common Name English
CONIINE, DL-
Common Name English
(±)-CONIINE
Common Name English
PIPERIDINE, 2-PROPYL-, (±)-
Systematic Name English
DL-CONIINE
Common Name English
Code System Code Type Description
CAS
3238-60-6
Created by admin on Sat Dec 16 09:02:45 GMT 2023 , Edited by admin on Sat Dec 16 09:02:45 GMT 2023
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FDA UNII
04R53ZF48T
Created by admin on Sat Dec 16 09:02:45 GMT 2023 , Edited by admin on Sat Dec 16 09:02:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
221-801-3
Created by admin on Sat Dec 16 09:02:45 GMT 2023 , Edited by admin on Sat Dec 16 09:02:45 GMT 2023
PRIMARY
PUBCHEM
9985
Created by admin on Sat Dec 16 09:02:45 GMT 2023 , Edited by admin on Sat Dec 16 09:02:45 GMT 2023
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EPA CompTox
DTXSID3046821
Created by admin on Sat Dec 16 09:02:45 GMT 2023 , Edited by admin on Sat Dec 16 09:02:45 GMT 2023
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