Cotinine

Base Information

• Chemical Name: Cotinine
• CAS No.: 486-56-6
• Molecular Formula: C10H12 N2 O
• Molecular Weight: 176.218
• Hs Code.: 29333990
• European Community (EC) Number: 207-634-9
• NSC Number: 756704
• UNII: K5161X06LL
• DSSTox Substance ID: DTXSID1047576
• Nikkaji Number: J6.013E
• Wikipedia: Cotinine
• Wikidata: Q421177
• NCI Thesaurus Code: C70941
• Metabolomics Workbench ID: 65144
• ChEMBL ID: CHEMBL578211
• Mol file: 486-56-6.mol

Synonyms:Cotinine;Scotine

Chemical Property of Cotinine

Chemical Property:

• Vapor Pressure: 0.000421mmHg at 25°C
• Melting Point: 40-42 °C(lit.)
• Refractive Index: 1.7110 (estimate)
• Boiling Point: 250 °C150 mm Hg(lit.)
• PKA: 4.72±0.12(Predicted)
• Flash Point: >230 °F
• PSA: 33.20000
• Density: 1.146g/cm³
• LogP: 1.31280
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)
• Water Solubility.: Not miscible or difficult to mix in water. Soluble in dimethyl sulfoxide (100 mM), ethanol (50 mg/ml, yielding a clear, faint ye
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 176.094963011
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cotinine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(CCC1=O)C2=CN=CC=C2
• Isomeric SMILES: CN1[C@@H](CCC1=O)C2=CN=CC=C2
• Recent NIPH Clinical Trials: Intervention study to decrease the environmental exposure to tobacco smoke in children
• Description: Cotinine is the major metabolite of nicotine. In the liver, nicotine is rapidly metabolized to cotinine (70–80%) by CYP2A6 and to nornicotine (5%) by CYP2A6 and CYP2B6. With a half-life about 10-fold longer than that of nicotine (15–19 h for cotinine versus 2–3 h for nicotine), cotinine induces plasma concentrations of 1–3 mM in smokers. After administration to rats, cotinine levels in the brain reach fourfold those of nicotine at 4 h following injection. Cotinine is not biotransformed in the brain, allowing accumulation of this substance to levels greater than that of nicotine. Like nicotine, cotinine is able to induce dopamine release in smokers and in superfused rat striatal slices in a dose- and calcium-dependent manner via the nicotinic receptors, but only at concentrations higher than those normally seen in smokers. Indeed, administration of cotinine to smokers at levels 10-fold that is seen following smoking had no observable effect, suggesting that cotinine is not neuroactive at doses found in smokers. However, cotinine also acts as an inhibitor for nicotine binding in rat brain via desensitization of the nicotinic receptor.
• Uses: antidepressant (-)-Cotinine is used to activate a subpopulation of α3/ α6β2 nAChRs in monkey striatum. It binds nicotinic- and muscarinic-type acetylcholine receptors with minimal receptor desensitization and demonstrates antipsychotic drug-like properties in behavioral models, neuroprotective properties in neurodegenerative disease models, and enhances attention in a delayed matching-to-sample task.

Technology Process of Cotinine

There total 21 articles about Cotinine 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: 98.4%

(S)-5‐(3‐pyridyl)tetrahydrofuran‐2‐one + methylammonium bromide (6876-37-5) → cotinine (486-56-6)

Guidance literature:

With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 100 ℃; for 12h; Temperature; Time; Reagent/catalyst;

Reference yield: 66.0%

2-Fluorobenzaldehyde (446-52-6) + nicotin (54-11-5) → C17H15FN2O + cotinine (486-56-6)

Guidance literature:

With Na₂Hg(II)edta; In water; for 1h; Inert atmosphere; Reflux;

DOI:10.1691/ph.2009.8785

Reference yield: 54.0%

4-nitrobenzaldehdye (555-16-8) + nicotin (54-11-5) → C17H15N3O3 + cotinine (486-56-6)

Guidance literature:

With Na₂Hg(II)edta; In ethanol; water; for 1h; Inert atmosphere; Reflux;

DOI:10.1691/ph.2009.8785

upstream raw materials:

(S)-3,3-dibromocotinine

3,3-dibromo-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one

nicotin

carbon monoxide

Downstream raw materials:

(3RS,5S)-1-Methyl-3-(phenylseleno)-5-(3-pyridyl)-2-pyrrolidinone

trans-3'-Hydroxycotinine

cis-(3'S,5'S)-3'-hydroxycotinine

nicotin

Refernces

• 1、 Yamamiya, Ikuo,Yoshisue, Kunihiro,Ishii, Yuji,Yamada, Hideyuki,Chiba, Masato. "Effect of CYP2A6 genetic polymorphism on the metabolic conversion of tegafur to 5-fluorouracil and its enantioselectivity". . p. 1485 - 1492. Retrieved 2014.
• 2、 Hosono, Hiroki,Kumondai, Masaki,Maekawa, Masamitsu,Yamaguchi, Hiroaki,Mano, Nariyasu,Oda, Akifumi,Hirasawa, Noriyasu,Hiratsuka, Masahiro. "Functional characterization of 34 CYP2A6 allelic variants by assessment of nicotine C-oxidation and coumarin 7-hydroxylation activities". . p. 279 - 285. Retrieved 2017.
• 3、 Moldoveanu, Serban C.. "Interconversion of nicotine enantiomers during heating and implications for smoke from combustible cigarettes, heated tobacco products, and electronic cigarettes". . p. 667 - 677. Retrieved 2022/02/02.
• 4、 -. "Preparation method of artificially synthesized nicotine". Paragraph 0078; 0083-0084. . Retrieved 2019/10/04.