2743-90-0

Basic information

• Product Name: (R,S)-ANATABINE
• Synonyms: D,L-ANATABINE;1,2,3,6-TETRAHYDRO-2,3'-BIPYRIDINE;(R,S)-ANATABINE;ANATABINE, (+/-)-(RG);(+/-)-Anatabine, 3-(1,2,3,6-Tetrahydropyridin-2-yl)pyridine, 2-(Pyridin-3-yl)-1,2,3,6-tetrahydropyridine;Anatabine, froM Nicotiana tabacuM L.;Anatabine, 97%, from Nicotiana tabacum L.
• CAS NO: 2743-90-0
• Molecular Formula: C₁₀H₁₂N₂
• Molecular Weight: 160.22
• Product Categories: Metabolites;Nicotine Derivatives;Aromatics;Heterocycles;Metabolites & Impurities
• Mol File: 2743-90-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 136
• Flash Point: 116.5 °C
• Appearance: Light Yellow Oil
• Density: 1.045 g/cm³
• Storage Temp.: Amber Vial, Refrigerator, Under Inert Atmosphere
• Solubility: ≤15mg/ml in DMSO;15mg/ml in dimethyl formamide
• PKA: 8.84±0.40(Predicted)
• Stability: Hygroscopic, Light Sensitive
• CAS DataBase Reference: (R,S)-ANATABINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-ANATABINE(2743-90-0)
• EPA Substance Registry System: (R,S)-ANATABINE(2743-90-0)

Safety Data

• Statements: 25-36
• Safety Statements: 24/25
• RIDADR: 2810
• HazardClass: IRRITANT
• Hazardous Substances Data: 2743-90-0(Hazardous Substances Data)

Usage

Description

(R,S)-Anatabine is a minor alkaloid found in plants of the Solanaceae family, including tobacco. It is a metabolite of nicotine and is used as an indicator of tobacco use when nicotine-containing products are also being used. This light yellow oil has been shown to increase nicotine self-administration and locomotor activity in rats, while also demonstrating potential therapeutic effects by reducing amyloid-β production and inhibiting NF-κB activation.

Uses

Used in Tobacco Use Detection:
(R,S)-Anatabine is used as a biomarker for tobacco use, particularly when individuals are using nicotine-containing products such as gum, patches, inhalers, and medications. The detection of (R,S)-anatabine in urine helps confirm tobacco consumption.
Used in Neurodegenerative Disease Research:
(R,S)-Anatabine is used as a research compound for studying its potential effects on neurodegenerative diseases. It has been shown to diminish amyloid-β production in vitro and in vivo, suggesting a possible role in the treatment or prevention of conditions like Alzheimer's disease.
Used in Pharmaceutical Research:
(R,S)-Anatabine is used as a compound in the development of new pharmaceuticals, particularly those targeting neurodegenerative diseases and tobacco addiction. Its ability to increase nicotine self-administration and inhibit NF-κB activation makes it a promising candidate for further research and development in these areas.

in vitro

anatabine dose-dependently lowered aβ1-40 and aβ1-42 levels and reduced sappβ production without any effects on sappα levels. anatabine lowered aβ production by mainly impacting the β-cleavage of app. anatabine lowered nfκb activation. anatabine inhibited bace-1 transcription and reduced bace-1 protein levels in human neuronal like shsy-5y cells. (r,s)-anatabine also dose dependently inhibits nf-κb activation [1].

in vivo

in a transgenic mouse model of alzheimer's disease, acute treatment with anatabine for 4 days significantly lowered brain soluble aβ1-40 and aβ1-42 levels [1].

references

[1] paris d, beaulieu-abdelahad d, bachmeier c, et al. anatabine lowers alzheimer's aβ production in vitro and in vivo[j]. european journal of pharmacology, 2011, 670(2): 384-391.

Upstream product

• 1027559-83-6 Benzhydrylidene-((Z)-5-chloro-1-pyridin-3-yl-pent-3-enyl)-amine 
• 3731-52-0 3-Aminomethylpyridine 
• 175441-83-5 N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine 
• 1236361-13-9 (+/-)-N-methylanatabine-N-oxide 
• 500-22-1 3-pyridinecarboxaldehyde 
• 1332337-77-5 N,N-(dimethylsulfamoyl)-3-pyridinylaldimine 
• 1332337-78-6 N'-(1-(pyridin-3-yl)-but-3-enyl)-N,N-dimethylsulfonamide 
• 1332337-79-7 N-(prop-2-en-1-yl)-1-(pyridin-3-yl)but-3-en-1-amine 
• 2524-49-4 3-butene-1-amine 
• 1159977-12-4 tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate 
• 1476-11-5 Z-1,4-dichlorobutene 
• 133692-30-5 N-allyl-1-(pyridin-3-yl)methanimine 

Downstream Products

• 581-50-0 2,3'-bipyridine 
• 13078-04-1 anabasine 
• 1159977-12-4 tert-butyl 3,6-dihydro-[2,3'-bipyridine]-1(2H)-carboxylate 

Relevant articles and documents

A Practical and Efficient Synthesis of (±)-Anatabine

A new efficient synthesis of racemic anatabine is reported. The title target was obtained in an excellent overall yield of 70%, by a five-step synthesis, using cheap reagents and mild reaction conditions.

Toward Pyridine-Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine

The formation of pyridine-containing bisheterocycles through a Prins-type cyclisation is described. Pyridine-tetrahydropyran and pyridine-piperidine conjugates could be efficiently obtained using various carbaldehydes including dicarbaldehydes, and either homoallylic alcohols or a homoallylic amine. Selective partial or complete hydrogenation led to new bisheterocycle combinations. A two-step sequence involving an aza-Prins cylisation allowed us to prepare the alkaloid anabasine.

METHODS OF SYNTHESIZING ANATABINE

Anatabine is obtained by reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine. The resulting anatabine is substantially free from contaminants and displays good stability. In an alternative embodiment, the benzylhydrylidene-pyridin-3-yl-methyl-amine may be used in the synthesis of other alkaloids such as anabasine, nornicotine, N-methylanabasine, and anabaseine.