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

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

Uses

Used in Pharmaceutical Industry:
Metanicotine is used as a potential therapeutic agent for the treatment of cognitive deficits in neurodegenerative disorders. Its application is based on its ability to improve cognitive function, as evidenced by its effects in animal models, and its potential to offer a new treatment option for cognitive impairments in humans.
Used in Research and Development:
In the field of scientific research, Metanicotine is used as a subject of study for its dual activity at nicotinic acetylcholine receptors. This dual activity makes it an intriguing candidate for exploring new avenues in the treatment of cognitive disorders, as well as for understanding the underlying mechanisms of these conditions.

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

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

Downstream Products

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

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.

Evaluation of structurally diverse neuronal nicotinic receptor ligands for selectivity at the α6* subtype

Direct comparison of pyridine versus pyrimidine substituents on a small but diverse set of ligands indicates that the pyrimidine substitution has the potential to enhance affinity and/or functional activity at α6 subunit-containing neuronal nicotinic rece

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

Transformations involving the Pyrrolidine Ring of Nicotine

Nicotine was oxidised to cotinine and this successively alkylated and reduced to a series of 4'-mono- and 4',4'-di-alkylnicotines, the mass spectra of which are discussed.The pyrrolidine ring has been opened with ethyl chloroformate and the product both recyclised to S-nicotine without loss of optical activity and converted to metanicotine.The dihydrochloride of the last, on successive treatment with bromine and sodium hydrogencarbonate, yielded 3'-bromonicotine.Cotinine has been converted into various derivatives, and the demethylation of nicotine has been investigated.