Altinicline

Base Information

• Chemical Name: Altinicline
• CAS No.: 179120-92-4
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.257
• UNII: RJ9V9V09VM
• DSSTox Substance ID: DTXSID40870143
• Nikkaji Number: J763.592C
• Wikipedia: Altinicline
• Wikidata: Q4736710
• NCI Thesaurus Code: C77841
• ChEMBL ID: CHEMBL111659
• Mol file: 179120-92-4.mol

Synonyms:5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate;altinicline maleate;SIB 1508Y;SIB-1508Y

Chemical Property of Altinicline

Chemical Property:

• Vapor Pressure: 0.00245mmHg at 25°C
• Boiling Point: 287.7°C at 760 mmHg
• PKA: 7.83±0.70(Predicted)
• Flash Point: 127.8°C
• PSA: 16.13000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 1.76750
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.115698455
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

98% ^*data from raw suppliers

5-EthynylNicotine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCC1C2=CN=CC(=C2)C#C
• Isomeric SMILES: CN1CCC[C@H]1C2=CN=CC(=C2)C#C
• Uses: An intermediate of nicotinic acetylcholine receptor agonist SIB-1508Y. Used for the treatment of neurological disorders 5-Ethynylnicotine is an intermediate of nicotinic acetylcholine receptor agonist SIB-1508Y. 5-Ethynylnicotine is used for the treatment of neurological disorders. SIB 1508Y is a neuronal nicotinic acetylcholine receptor agonist. In rat studies, SIB 1508Y increased dopamine release and showed antidepressant activity. SIB 1508Y is an anti-Parkinson''s agent.

Technology Process of Altinicline

There total 22 articles about Altinicline 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%

(S)-5-[(triisopropylsilyl)ethynyl]nicotine (916046-39-4) → altinicline (179120-92-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1021/jo0616052

Reference yield: 97.0%

2-Methyl-4-[5-((S)-1-methyl-pyrrolidin-2-yl)-pyridin-3-yl]-but-3-yn-2-ol (179120-91-3) → altinicline (179120-92-4)

Guidance literature:

With sodium hydride; In toluene;

DOI:10.1021/jm960328w

Reference yield: 51.0%

(S)-nicotine-5-carboxaldehyde (852238-97-2) → altinicline (179120-92-4)

Guidance literature:

dimethyl diazomethylphosphonate; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

(S)-nicotine-5-carboxaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 18h;

upstream raw materials:

2-Methyl-4-[5-((S)-1-methyl-pyrrolidin-2-yl)-pyridin-3-yl]-but-3-yn-2-ol

(S)-nicotine-5-carboxaldehyde

dimethyl diazomethylphosphonate

(S)-5-[(triisopropylsilyl)ethynyl]nicotine

Refernces

• 1、 Barker, Graeme,McGrath, Julia L.,Klapars, Artis,Stead, Darren,Zhou, George,Campos, Kevin R.,O'Brien, Peter. "Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: In situ react IR spectroscopic monitoring, scope, and synthetic applications". experimental part. p. 5936 - 5953. Retrieved 2011/10/09.
• 2、 -. "Synthesis of nicotine derivatives from nicotine". Page/Page column 8; 10. . Retrieved 2008/06/13.