nicotine-1'-N-oxide

Base Information

• Chemical Name: nicotine-1'-N-oxide
• CAS No.: 491-26-9
• Deprecated CAS: 22588-95-0
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.234
• UNII: 9R173T257I
• DSSTox Substance ID: DTXSID70867021
• Nikkaji Number: J124.167B
• Wikidata: Q27272930
• ChEMBL ID: CHEMBL3544718
• Mol file: 491-26-9.mol

Synonyms:nicotine 1-N-oxide;nicotine 1-N-oxide, (1R-cis)-isomer;nicotine 1-N-oxide, (1R-trans)-isomer;nicotine 1-N-oxide, (1S-cis)-isomer;nicotine 1-N-oxide, (1S-trans)-isomer;nicotine 1-N-oxide, (2S)-isomer;nicotine 1-N-oxide, (R)-isomer;nicotine 1-N-oxide, (S)-isomer;nicotine 1-N-oxide, 14C-labeled cpd;nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer;nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer;nicotine 1-N-oxide, dihydrochloride, (S)-isomer;nicotine-1'-N-oxide;nicotine-1'-oxide

Chemical Property of nicotine-1'-N-oxide

Chemical Property:

• PSA: 42.32000
• LogP: 1.81970
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 178.110613074
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

99%, ^*data from raw suppliers

(1'S,2'S)-NICOTINE 1'-OXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(CCCC1C2=CN=CC=C2)[O-]
• Isomeric SMILES: C[N+]1(CCC[C@H]1C2=CN=CC=C2)[O-]
• Uses: Nicotine-N''-oxide is is used as a reactant in the preparation and cyanation of nicotine derivatives and analogs and use in stimulating α7 nAChR and/or α4β2 receptors

Technology Process of nicotine-1'-N-oxide

There total 6 articles about nicotine-1'-N-oxide 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: 97.0%

nicotin (54-11-5) → nicotine-1'-N-oxide (29419-54-3,29419-55-4,51020-67-8,51095-86-4,491-26-9,63551-14-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/jhet.841

Reference yield: 27.5%

nicotin (54-11-5) → nornicotine (494-97-3,13450-58-3) + S-(-)-Norcotinine (5980-06-3,17114-40-8) + cotinine (486-56-6) + Nicotine-N-oxide (491-26-9,29419-54-3,29419-55-4,51020-67-8,51095-86-4,63551-14-4)

Guidance literature:

With air; cofactor solution; phenobarbitone-induced rabbit hepatic homogenate; In phosphate buffer; at 37 ℃; for 1h; pH=7.4; Further byproducts given;

DOI:10.1002/(SICI)1099-1344(199904)42:4<387::AID-JLCR203>3.0.CO;2-5

Reference yield:

3-(1-methyl-pyrrolidin-2-yl)-pyridine (22083-74-5) → Nicotine-N-oxide (491-26-9,29419-54-3,29419-55-4,51020-67-8,51095-86-4,63551-14-4)

Guidance literature:

With dihydrogen peroxide; platinum;

upstream raw materials:

3-(1-methyl-pyrrolidin-2-yl)-pyridine

nicotin

Downstream raw materials:

3-(1-methyl-pyrrolidin-2-yl)-pyridine

nicotin

nicotinic acid

5'-cyanonicotine

Refernces

• 1、 Dickerson, Tobin J.,Yamamoto, Noboru,Janda, Kim D.. "Antibody-catalyzed oxidative degradation of nicotine using riboflavin". . p. 4981 - 4987. Retrieved 2007/10/03.
• 2、 Chaudhary, Shveta,Awasthi, Abha,Chauhan, S. M. S.. "Biomimetic oxidation of nicotine with hydrogen peroxide and 5-ethylflavin mononucleotide perchlorate". . p. 294 - 297. Retrieved 2007/10/03.