Nicotyrine

Base Information

• Chemical Name: Nicotyrine
• CAS No.: 487-19-4
• Deprecated CAS: 30813-25-3
• Molecular Formula: C10H10 N2
• Molecular Weight: 158.203
• Hs Code.: 2939800000
• European Community (EC) Number: 207-651-1
• NSC Number: 407276,127943
• UNII: XN4R1LH79Y
• DSSTox Substance ID: DTXSID3075048
• Nikkaji Number: J6.018F
• Wikipedia: Nicotyrine
• Wikidata: Q1987338
• Metabolomics Workbench ID: 67593
• ChEMBL ID: CHEMBL1522291
• Mol file: 487-19-4.mol

Synonyms:2-(1-methyl-2-pyrryl)pyridine;alpha-nicotyrine;beta-nicotyrine

Chemical Property of Nicotyrine

Chemical Property:

• Vapor Pressure: 0.00561mmHg at 25°C
• Melting Point: 168-169 °C
• Refractive Index: 1.6057 (estimate)
• Boiling Point: 282.8°Cat760mmHg
• PKA: pK1:4.76(+1) (25°C)
• Flash Point: 124.8°C
• PSA: 17.82000
• Density: 1.04g/cm³
• LogP: 2.08710
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Met
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 158.084398327
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

99%, ^*data from raw suppliers

β-Nicotyrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=CC=C1C2=CN=CC=C2
• Description: The occurrence of this alkaloid in the cigar type of tobacco has been reported by Wenusch and subsequently confirmed by Spath and Kesztler. It forms a colour_x0002_less oil when pure and yields crystalline salts and derivatives, e.g. the p1atinichloride, m.p. 158°C; picrate, m.p. 170-1 °c and the methiodide, m.p. 2l1-3°e. It may also be prepared from nicotine by oxidation with silver oxide, silver acetate or potassium ferricyanide. With Zn and HCI, the base is reduced to nicotine and 4:5-dihydronicotyrine, b.p. 244-6°C, yielding a dipicrate, m.p. l64°e. In the presence of prepared Pt02, the latter may be further reduced to dihydrometanicotine, the dipicrate of which has m.p. 161-2°C. Nicotyrine may be converted directly into nicotine in one operation by controlled hydrogenation in the presence on Pd-e
• Uses: Nicotryrine is an alkaloid derived from the dehydrogenation of nicotine and its analog, nornicotine. An alkaloid occurring in cigaret smoke.

Technology Process of Nicotyrine

There total 62 articles about Nicotyrine 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: 98.0%

methylamine (74-89-5) + 4-Oxo-1-(3-pyridyl)-1-butanone (76014-80-7) → nicotirine (487-19-4)

Guidance literature:

In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/b109482n

Reference yield: 87.0%

bis-1-methyl-2-(3-pyridyl)pyrrol-3-yl disulphide (73671-58-6) → nicotirine (487-19-4)

Guidance literature:

With sodium hydroxide; nickel; In tetrahydrofuran; for 2h; Heating;

Reference yield: 85.0%

3-Bromopyridine (626-55-1,163928-56-1) + 1-Methyl-2-pyrrolecarboxylic acid (6973-60-0) → nicotirine (487-19-4)

Guidance literature:

With tetrabutyl-ammonium chloride; caesium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 170 ℃; for 0.133333h; microwave irradiation;

DOI:10.1021/ja063511f

upstream raw materials:

tetrachloromethane

1-methyl-2-(3-pyridyl)-3-pyrroline

ethylene glycol

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

Downstream raw materials:

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

Refernces

• 1、 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.
• 2、 Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.. "A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry". . p. 12822 - 12828. Retrieved 2020/12/29.