(-)-Anabasine

Base Information

• Chemical Name: (-)-Anabasine
• CAS No.: 494-52-0
• Molecular Formula: C10H14 N2
• Molecular Weight: 162.235
• Hs Code.: 29333990
• European Community (EC) Number: 207-791-3
• NSC Number: 87504
• UNII: LMS11II2LO
• DSSTox Substance ID: DTXSID9041607
• Nikkaji Number: J3.284K
• Wikipedia: Anabasine
• Wikidata: Q419308
• NCI Thesaurus Code: C124073
• Metabolomics Workbench ID: 52796
• ChEMBL ID: CHEMBL1526229
• Mol file: 494-52-0.mol

Synonyms:Anabasine;Neonicotine

Chemical Property of (-)-Anabasine

Chemical Property:

• Appearance/Colour: White fine crystalline powder
• Vapor Pressure: 0.00662mmHg at 25°C
• Melting Point: 9°C
• Refractive Index: 1.5430
• Boiling Point: 271 °C at 760 mmHg
• PKA: 8.98±0.10(Predicted)
• Flash Point: 93 ºC
• PSA: 24.92000
• Density: 1.054
• LogP: 2.22500
• Storage Temp.: Refrigerator
• 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:

99.9% ^*data from raw suppliers

(S)-Anabasine,>98%ee ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 27/28-51/53-23/24/25
• Safety Statements: 28-36/37-45-61-36/37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CCNC(C1)C2=CN=CC=C2
• Isomeric SMILES: C1CCN[C@@H](C1)C2=CN=CC=C2
• Uses: (S)-ANABASINE is used as a kind of Nicotinic receptor agonist. Anabasine occurs in the tobacco speciesNicotiana glauca, Anabasis aphylla L.,Chenopodiaceae, and Solanaceae. It is usedas an insecticide and as a metal anticorrosiveagent.

Technology Process of (-)-Anabasine

There total 44 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: 95.0%

C10H13BrN2 (1270360-24-1) → Anabasine (494-52-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; Schlenk technique;

DOI:10.1021/ja511422q

Reference yield: 95.0%

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester (121675-95-4) → 2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose (135865-76-8,135865-81-5,144102-44-3,148968-87-0,150737-36-3) + Anabasine (494-52-0)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1021/jo00279a001

Reference yield: 84.0%

(2S)-N-4'-nitrobenzoyl-2-(3-pyridyl)-4-piperidine (40179-50-8) → Anabasine (494-52-0)

Guidance literature:

With hydrogen bromide; acetic acid; at 80 ℃; for 45h;

DOI:10.1023/A:1010335003297

upstream raw materials:

anatabine

anabasine

(2S)-N-benzyl-2-(3-pyridyl)-piperidine

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(Ξ)-1-((S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridyl-1-yl)-propan-2-ol

(2S)-N-benzyl-2-(3-pyridyl)-piperidine

N-(methoxycarbonyl)anabasine

2,3'-bipyridine

Refernces

• 1、 Guo, Cui,Sun, Dong-Wei,Yang, Shuang,Mao, Shen-Jie,Xu, Xiao-Hua,Zhu, Shou-Fei,Zhou, Qi-Lin. "Iridium-catalyzed asymmetric hydrogenation of 2-pyridyl cyclic imines: A highly enantioselective approach to nicotine derivatives". . p. 90 - 93. Retrieved 2015.
• 2、 Bregier-Jarz?bowska, Romualda,Malczewska-Jaskó?a, Karolina,Jankowski, Wojciech,Jasiewicz, Beata,Hoffmann, Marcin,G?sowska, Anna,Jastrz?b, Renata. "Experimental and quantum-chemical studies of anabasine complexes with copper(II) and zinc(II) ions". . p. 841 - 848. Retrieved 2015/02/19.