Nornicotine

Base Information

• Chemical Name: Nornicotine
• CAS No.: 5746-86-1
• Molecular Formula: C9H12 N2
• Molecular Weight: 148.208
• Hs Code.: 29399990
• European Community (EC) Number: 637-353-0
• DSSTox Substance ID: DTXSID50862034
• Nikkaji Number: J391.269H
• Wikipedia: Nornicotine
• Wikidata: Q907939
• NCI Thesaurus Code: C190692
• Pharos Ligand ID: FMBN452CL42M
• ChEMBL ID: CHEMBL1132
• Mol file: 5746-86-1.mol

Synonyms:3-(2-pyrrolidinyl)pyridine;nornicotine;nornicotine tartrate, (S)-(R-(R*,R*))-isomer;nornicotine, (R)-isomer;nornicotine, (S)-isomer

Chemical Property of Nornicotine

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.00702mmHg at 25°C
• Melting Point: 235-236 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.54
• Boiling Point: 107-108°C 2mm
• PKA: 9.09±0.10(Predicted)
• Flash Point: 101°C
• PSA: 24.92000
• Density: 1,074 g/cm³
• LogP: 1.83490
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: Soluble in acetone, chloroform and water (50mg/ml).
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 148.100048391
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

(R,S)-Nornicotine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:; R36/37/38:
• Hazard Codes: Xn,Xi,T,F
• Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CC(NC1)C2=CN=CC=C2
• Description: (±)-Nornicotine is a metabolite of nicotine that acts as a neuronal nicotinic acetylcholine receptor (nAChR) agonist. The α6 and α7 subunit-containing neuronal nAChRs are particularly responsive to nornicotine with EC50 values of approximately 4 and 17 μM, respectively, when expressed in Xenopus oocytes. Nornicotine promotes cell migration and destabilizes cell-cell junctions in an endothelial cell line. It is generally thought to be free from abuse potential, but it has been self-administered by rats. It can be detected in urine.
• Uses: A metabolite of Nicotine ((N412420). Can catalyze aqueous aldol reactions. 3-(2-Pyrrolidinyl)pyridine is a tobacco alkaloid and the major Nicotine (N412420) metabolite in brain. Nornicotine appears to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than Nicotine. Nornicotine shows a significant analgesic activity. Nicotine USP Related Compound F (3-(pyrrolidine-2-yl)pyridine). A metabolite of Nicotine. Can catalyze aqueous aldol reactions

Technology Process of Nornicotine

There total 51 articles about Nornicotine 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: 84.7%

Myosmine (532-12-7) → rac-nornicotine (5746-86-1,13450-58-3)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; for 5h;

Reference yield: 84.7%

myosmine (1125-96-8) → rac-nornicotine (5746-86-1,13450-58-3)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; for 5h; under 760.051 Torr;

Reference yield: 76.0%

4-oxo-4-(pyridin-3-yl)butanenitrile (36740-10-0) → rac-nornicotine (5746-86-1,13450-58-3)

Guidance literature:

4-oxo-4-(pyridin-3-yl)butanenitrile; With ammonia; In ethanol; at -80 - -75 ℃;

With hydrogen; for 36h; under 1520.1 Torr;

With sodium tetrahydroborate; for 1h; Reflux;

upstream raw materials:

Myosmine

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

3-(1-Hydroxy-2-pyrrolidinyl)pyridine

2,2,5,5-tetrametyl-1-aza-2,5-disilacyclopentane-1-propyl magnesium bromide

Downstream raw materials:

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

nornicotine

(+)-nornicotine

N'-formylnornicotine

Refernces

• 1、 -. "Synthesis method of (R, S-) nicotine". Paragraph 0046-0047. . Retrieved 2021/05/05.
• 2、 -. "ENANTIOMERIC SEPARATION OF RACEMIC NICOTINE BY ADDITION OF AN O,O'-DISUBSTITUTED TARTARIC ACID ENANTIOMER". Page/Page column 8; 17. . Retrieved 2019/07/13.