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Details

Stereochemistry ACHIRAL
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of METANICOTINE

SMILES

CNCCC=CC1=CN=CC=C1

InChI

InChIKey=JUOSGGQXEBBCJB-GORDUTHDSA-N
InChI=1S/C10H14N2/c1-11-7-3-2-5-10-6-4-8-12-9-10/h2,4-6,8-9,11H,3,7H2,1H3/b5-2+

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Rivanicline (also known as RJR-2403 or TC-2403) is a partial neuronal nicotinic acetylcholine receptor agonist. This compound binds primarily to the α4β2 receptor subtype. Rivanicline was originally developed for Alzheimer’s disease and shows pronounced anti-amnesic and increased recognition memory in rats. Because rivanicline also inhibits Interleukin-8 production, it has been further developed as a potential anti-inflammatory treatment for ulcerative colitis (in which nicotine is of therapeutic value but has adverse events). Rivanicline effectively inhibited TNF- and LPS-induced IL-8 production in different cell types, without toxic effects. Rivanicline was also evaluated as a potential compound for the development of nicotinic therapeutics to treat neurological diseases in cases of compromised cholinergic neurotransmission.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [Ki]
46.0 µM [EC50]
PubMed

PubMed

TitleDatePubMed
(E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa.
2007-03
Antiamnestic effect of alpha7-nicotinic receptor agonist RJR-2403 in middle-aged ovariectomized rats with Alzheimer type dementia.
2006-12
3-(4-Aminobutyn-1-yl)pyridines: binding at alpha 4 beta 2 nicotinic cholinergic receptors.
2004-01-19
Nicotinic acetylcholine receptor regulation of spinal norepinephrine release.
2002-06
Synthesis of (+/-)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines.
2001-12
Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia.
1999-11
RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization.
1996-12
RJR-2403: a nicotinic agonist with CNS selectivity I. In vitro characterization.
1996-12
Patents
Substance Class Chemical
Created
by admin
on Wed Apr 02 00:59:55 GMT 2025
Edited
by admin
on Wed Apr 02 00:59:55 GMT 2025
Record UNII
VT98O71A2D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METANICOTINE
Common Name English
3-BUTEN-1-AMINE, N-METHYL-4-(3-PYRIDINYL)-
Preferred Name English
PYRIDINE, 3-(4-(METHYLAMINO)-1-BUTENYL)-
Systematic Name English
NSC-66331
Code English
Code System Code Type Description
CAS
538-79-4
Created by admin on Wed Apr 02 00:59:55 GMT 2025 , Edited by admin on Wed Apr 02 00:59:55 GMT 2025
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NSC
66331
Created by admin on Wed Apr 02 00:59:55 GMT 2025 , Edited by admin on Wed Apr 02 00:59:55 GMT 2025
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PUBCHEM
72928
Created by admin on Wed Apr 02 00:59:55 GMT 2025 , Edited by admin on Wed Apr 02 00:59:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID60864600
Created by admin on Wed Apr 02 00:59:55 GMT 2025 , Edited by admin on Wed Apr 02 00:59:55 GMT 2025
PRIMARY
FDA UNII
VT98O71A2D
Created by admin on Wed Apr 02 00:59:55 GMT 2025 , Edited by admin on Wed Apr 02 00:59:55 GMT 2025
PRIMARY