Vesamicol

Base Information

• Chemical Name: Vesamicol
• CAS No.: 112709-59-8
• Molecular Formula: C17H25 N O
• Molecular Weight: 259.392
• UNII: I1A877466V,3D416V0FLM
• DSSTox Substance ID: DTXSID20920872
• Nikkaji Number: J404.506H
• Wikipedia: Vesamicol
• Pharos Ligand ID: RY2KT1NT8L3W
• ChEMBL ID: CHEMBL20730
• Mol file: 112709-59-8.mol

Synonyms:2-(4-phenyl-1-piperidinyl)cyclohexanol;2-(4-phenylpiperidino)cyclohexanol;AH 5183;AH-5183;methylvesamicol;vesamicol;vesamicol hydrochloride;vesamicol hydrochloride, (+,-)-;vesamicol, (+,-)-

Chemical Property of Vesamicol

Chemical Property:

• Vapor Pressure: 6.73E-07mmHg at 25°C
• Melting Point: 238.5-240.0 °C
• Boiling Point: 393.5°Cat760mmHg
• PKA: 15.16±0.40(Predicted)
• Flash Point: 97°C
• PSA: 23.47000
• Density: 1.086g/cm³
• LogP: 3.90940
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 259.193614421
• Heavy Atom Count: 19
• Complexity: 266

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)N2CCC(CC2)C3=CC=CC=C3)O
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)N2CCC(CC2)C3=CC=CC=C3)O

Technology Process of Vesamicol

There total 4 articles about Vesamicol 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: 97.0%

(1R,2R)-2-(4-phenyl-1,2,5,6-tetrahydropyridin-1-yl)cyclohexanol → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 12h;

DOI:10.1016/j.tetasy.2004.03.002

Reference yield: 43.0%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-(1S,2S)-2-(4-phenylpiperidin-1-yl)cyclohexanol (112709-60-1,22232-64-0) → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0) + (+)-Vesamicol (112709-60-1,22232-64-0) + (1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexyl acetate

Guidance literature:

With Pseudomonas cepacia lipase; In various solvent(s); at 28 ℃; for 29h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2004.03.002

Reference yield:

4-phenylpiperidine (771-99-3) + cyclohexane-1,2-epoxide (286-20-4) → (-)-vesamicol (112709-59-8,112709-60-1,22232-64-0) + (+)-Vesamicol (112709-60-1,22232-64-0)

Guidance literature:

In ethanol; for 22h; Yield given; Heating;

DOI:10.1021/jm00126a013

upstream raw materials:

4-phenylpiperidine

cyclohexane-1,2-epoxide

vinyl acetate

(+/-)-(1S,2S)-2-(4-phenylpiperidin-1-yl)cyclohexanol

Downstream raw materials:

(1R,2R)-2-[4-(4-Amino-phenyl)-piperidin-1-yl]-cyclohexanol

Refernces

3D QSAR study, synthesis, and in vitro evaluation of (+)-5-FBVM as potential PET radioligand for the vesicular acetylcholine transporter (VAChT)

10.1016/j.bmc.2010.08.028

The study focuses on the 3D QSAR (Quantitative Structure-Activity Relationship) analysis, synthesis, and in vitro evaluation of (+)-5-FBVM, a potential PET (Positron Emission Tomography) radioligand for the vesicular acetylcholine transporter (VAChT), which is a significant target for early detection of cholinergic neuron degeneration in Alzheimer's disease. The researchers conducted QSAR studies on vesamicol and benzovesamicol derivatives, considering the stereoselectivity of the VAChT binding site, and identified both enantiomers of 5-FBVM as promising candidates with predicted VAChT affinities between 6.1 and 0.05 nM. They synthesized enantiopure (R,R)- and (S,S)-5-FBVM and their corresponding triazene precursors for future radiofluorination. The in vitro evaluation revealed high affinity and selectivity for VAChT, with (+)-5-FBVM showing particular promise for further investigation as a potential radioligand for in vivo PET imaging of cholinergic nerve terminals.

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