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%,99%, ^*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
• Description: Anatabine is an alkaloid found in the root, fibrous roots, or bark of Alangium chinense (Lour) Harms. The herb was recorded in “Jianyi Bencao,” “Bencao Gangmu Shiyi,” and “Zhi Wu Ming Shi Tu Kao.” Alangium chinense is widely distributed in the east and south of China. It is also called “Bailongxu” in Shaanxi, Yunnan, and Guizhou provinces, “Baijintiao” in Guangxi province, and “Bajiaowutong,” “Bajiaojinpan,” or “Laolongxu” in Jiangxi and Hubei provinces. This plant is commonly used as a traditional Chinese medicine. The Alangium species includes more than 30 plants which are distributed in Asia, Oceania, and Africa. Nine of these plants are distributed in China. The root and the stem parts of Alangium plants are toxic.
• Physical properties: Appearance: Colorless to yellow liquid. Solubility: Soluble in water and common organic solvents. Boiling point: 110?°C. Refractive index: 1.5418. Density: 1.0516?g cm?3.
• Uses: Anabasine, a tobacco alkaloid, was used as a biomarker of active tobacco use. A nicotinic receptor agonist insecticide
• Clinical Use: The Alangium chinense was used for treating rheumatoid arthritis.

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

Refernces

• 1、 Yang, Chi-Ming,Tanner, Dennis D.. "A simple synthesis of (±)-1,2,3,6-tetrahydro-2,3′-bipyridine (anatabine) and (±)-3-(2-piperidinyl)pyridine (anabasine) from lithium aluminum hydride and pyridine". . p. 616 - 620. Retrieved 1997.
• 2、 Smith. "-". . p. 277,279. Retrieved 1931.
• 3、 Colin, Olivier,Greck, Christine,Prim, Damien,Thomassigny, Christine. "Toward Pyridine-Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine". . p. 7000 - 7005. Retrieved 2016/02/19.