Anabasine

Base Information

• Chemical Name: Anabasine
• CAS No.: 13078-04-1
• Molecular Formula: C10H14N2
• Molecular Weight: 162.235
• Hs Code.: 29339900
• European Community (EC) Number: 207-791-3,621-972-8
• DSSTox Substance ID: DTXSID50859409
• Nikkaji Number: J849.758C
• Wikipedia: Anabasine
• Wikidata: Q97463797
• NCI Thesaurus Code: C124073
• Pharos Ligand ID: GCWXXBW5XWGK
• Metabolomics Workbench ID: 130016
• ChEMBL ID: CHEMBL280963
• Mol file: 13078-04-1.mol

Synonyms:Anabasine;Neonicotine

Chemical Property of Anabasine

Chemical Property:

• Appearance/Colour: colourless oil
• Vapor Pressure: 0.00662mmHg at 25°C
• Melting Point: 9 °C
• Refractive Index: 1.5440
• Boiling Point: 271 °C at 760 mmHg
• PKA: 8.98±0.10(Predicted)
• Flash Point: 93.3 °C
• PSA: 24.92000
• Density: 1.014 g/cm³
• LogP: 2.22500
• Storage Temp.: Refrigerator
• Solubility.: H2O: 10 mg/mL
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.115698455
• Heavy Atom Count: 12
• Complexity: 136

Purity/Quality:

≥98% ^*data from raw suppliers

(R,S)-Anabasine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• Statements: 23/24/25-36/37/38-25-20/21/22-51/53-27/28
• Safety Statements: 36/37/39-45-26-36-57-27/28-23-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CCNC(C1)C2=CN=CC=C2
• General Description: (-)-Anabasine, also known as DL-anabasine or 3-(2-piperidinyl)pyridine, is a tobacco alkaloid structurally related to nicotine. It can be synthesized through various methods, including the Schmidt reaction applied to tertiary alcohols, base-catalyzed condensation of dihydropyridines, or via Barbier-type allylation and ring-closing metathesis. (-)-ANABASINE has been characterized by NMR spectroscopy, with full spectral assignments reported. Anabasine forms as a racemate in some synthetic routes, such as the hydrogenation of anatabine or the reaction of dihydropyridines under oxidative conditions. Its synthesis and structural elucidation contribute to the broader understanding of tobacco alkaloids.

Technology Process of Anabasine

There total 21 articles about Anabasine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-butyl 2-(pyridine-3-yl)piperidine-1-carboxylate (154874-91-6) → anabasine (13078-04-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ol801579r

Reference yield: 95.0%

anabaseine (3471-05-4) → anabasine (13078-04-1)

Guidance literature:

With sodium cyanoborohydride; In methanol; other reagent: H₂ with Pd/C;

DOI:10.1016/S0040-4039(00)81810-9

Reference yield: 83.0%

(+/-)-Anatabine (2743-90-0,126454-22-6) → anabasine (13078-04-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 3h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2011.06.093

upstream raw materials:

pyridine

Anabasine

2,3,4,5-tetrahydropyridine

3-Bromopyridine

Downstream raw materials:

N-Benzoylanabasin

Anabasine

N-Nitrosoanabasine

tert-butyl 2-(pyridine-3-yl)piperidine-1-carboxylate