538-79-4

Basic information

• Product Name: metanicotine
• Synonyms: 3-[4-(Methylamino)-1-butenyl]pyridine;3-Buten-1-amine, N-methyl-4-(3-pyridinyl)- (9ci);Ai3-18211;Nsc 66331;Pyridine, 3-(4-(methylamino)-1-butenyl)-;N-Methyl-4-(3-pyridinyl)-3-buten-1-amine;TC-2403;TC-2403-12
• CAS NO: 538-79-4
• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.26
• Mol File: 538-79-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 292℃
• Flash Point: 130℃
• Appearance: /
• Density: 0.980
• Vapor Pressure: 0.0019mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• CAS DataBase Reference: metanicotine(CAS DataBase Reference)
• NIST Chemistry Reference: metanicotine(538-79-4)
• EPA Substance Registry System: metanicotine(538-79-4)

Safety Data

• Hazardous Substances Data: 538-79-4(Hazardous Substances Data)

Usage

General Description

Metanicotine is a chemical compound that is a partial agonist at both the α7 nicotinic acetylcholine receptor and the α3β4 nicotinic acetylcholine receptor. It is being studied for its potential use in treating cognitive deficits associated with neurodegenerative disorders such as Alzheimer's disease and schizophrenia. Metanicotine has been shown to improve cognitive function in animal models and is being considered as a potential therapeutic option for treating cognitive impairments in humans. Its dual activity at nicotinic acetylcholine receptors makes it an interesting candidate for further research and development.

InChI:InChI=1/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+

Upstream product

• 312728-39-5 (3E)-N-methyl-N-(tert-butoxycarbonyl)-4-(3-pyridinyl)-3-buten-1-amine 
• 3156-52-3 3-(2-nitroethenyl)pyridine 
• 212332-33-7 (E)-4-(3-pyridinyl)-3-butene-1-amine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 73130-52-6 ethyl N-methyl-N-<4-chloro-4-(3-pyridyl)butnyl>carbamate 
• 7647-01-0 hydrogenchloride 
• 7782-99-2 sulphurous acid 
• 54002-25-4 ethyl N-methyl-N-<4-(3-pyridyl)but-3-enyl>carbamate 
• 23158-10-3 N-methyl-N-(4-pyridin-3-yl-but-3-enyl)-benzamide 
• 2055-27-8 4-methylamino-1-[3]pyridyl-butan-1-ol 

Downstream Products

• 539-32-2 3-butylpyridine 
• 887250-41-1 E-metanicotine 3,5-dihydroxybenzoate 
• 887250-40-0 E-metanicotine 2,5-dihydroxybenzoate 
• 74-89-5 methylamine 
• 3000-74-6 dihydrometanicotine 

Relevant articles and documents

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.

Radiosynthesis and PET studies of [11C]RJR-2403, a nicotinic agonist

(E)-N-methyl-4-(3-pyridinyl)-3-butene-1-amine (RJR-2403, or metanicotine), a nicotinic agonist developed as a cognitive-enhancing drug for Alzheimer's disease, was labeled with carbon-11 using [11C]methyl iodide via a simple and efficient one-step procedure. Regioselectivity of [11C]methylation on the aliphatic nitrogen versus pyridine nitrogen is strongly dependent on the reaction solvent. The reaction in acetonitrile exclusively yields aliphatic N-[11C-methyl]alkylation ([11C]RJR-2403), while only a byproduct is formed when DMF is used as a solvent. Positron emission tomographic (PET) studies in baboon showed a homogeneous distribution of radioactivity within baboon brain with a slow clearance. [11C]RJR-2403 was metabolized very rapidly as evidenced by the fact that at 2 min after intravenous injection only 50% of the total carbon-11 in plasma is parent compound. Copyright