Demethylcotinine

Base Information

• Chemical Name: Demethylcotinine
• CAS No.: 5980-06-3
• Molecular Formula: C9H10 N2 O
• Molecular Weight: 162.191
• UNII: 8QA8709E9J
• Nikkaji Number: J419.577I
• Wikidata: Q27270898
• ChEMBL ID: CHEMBL3544719
• Mol file: 5980-06-3.mol

Synonyms:demethylcotinine;5980-06-3;(5S)-5-pyridin-3-ylpyrrolidin-2-one;(S)-5-Pyridin-3-yl-pyrrolidin-2-one;(S)-5-(Pyridin-3-yl)pyrrolidin-2-one;8QA8709E9J;(5s)-5-(pyridin-3-yl)pyrrolidin-2-one;(-)-DEMETHYLCOTININE;UNII-8QA8709E9J;CHEMBL3544719;SCHEMBL13035251;BDBM109775;US8609708, 84 Norcotinine;(S)-5-(3-Pyridinyl)-2-pyrrolidinone;CS-0341752;2-Pyrrolidinone, 5-(3-pyridinyl)-, (S)-;2-Pyrrolidinone, 5-(3-pyridinyl)-, (5S)-;Q27270898

Chemical Property of Demethylcotinine

Chemical Property:

• Vapor Pressure: 1.5E-06mmHg at 25°C
• Boiling Point: 398.2°C at 760 mmHg
• Flash Point: 194.6°C
• PSA: 41.99000
• Density: 1.169g/cm³
• LogP: 1.36150
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.079312947
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

(S)-5-Pyridin-3-yl-pyrrolidin-2-one 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1C2=CN=CC=C2
• Isomeric SMILES: C1CC(=O)N[C@@H]1C2=CN=CC=C2

Technology Process of Demethylcotinine

There total 8 articles about Demethylcotinine 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: 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:

5-(pyridin-3-yl)pyrrolidin-2-one (17708-87-1,17114-40-8) → S-(-)-Norcotinine (5980-06-3,17114-40-8)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1021/ja01524a034

Reference yield:

4-oxo-4-(pyridin-3-yl)butanoic acid (4192-31-8) → S-(-)-Norcotinine (5980-06-3,17114-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Raney nickel; ethanol; NH₃ / 130 °C / 58840.6 Torr / Hydrogenation

2: (1S)-2-oxo-bornane-10-sulfonic acid

With ethanol; camphor-10-sulfonic acid; ammonia; nickel;

DOI:10.1021/ja01524a034

upstream raw materials:

5-(pyridin-3-yl)pyrrolidin-2-one

nicotin

4-oxo-4-(pyridin-3-yl)butanoic acid

dimethyl 2-[(pyridin-3-yl)methylidene]malonate

Refernces

• 1、 Tsai, Mui-Chiung,Sai, Yang,Li, Yan,Aislaitner, George,Gorrod, John W.. "The biosynthesis of [5'-14C]cotinine and other radiolabeled nicotine metabolites". . p. 387 - 407. Retrieved 2007/10/03.