Guvacine

Base Information

• Chemical Name: Guvacine
• CAS No.: 498-96-4
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.143
• UNII: 41538P325K
• DSSTox Substance ID: DTXSID50871702
• Nikkaji Number: J11.591F
• Wikipedia: Guvacine
• Wikidata: Q15322708
• Metabolomics Workbench ID: 67456
• ChEMBL ID: CHEMBL76768
• Mol file: 498-96-4.mol

Synonyms:guvacine;guvacine hydrobromide;guvacine hydrochloride

Chemical Property of Guvacine

Chemical Property:

• Vapor Pressure: 0.000983mmHg at 25°C
• Melting Point: 295°C (rough estimate)
• Refractive Index: 1.4645 (estimate)
• Boiling Point: 280.8°Cat760mmHg
• PKA: 3.61±0.20(Predicted)
• Flash Point: 123.6°C
• PSA: 49.33000
• Density: 1.199g/cm³
• LogP: 1.12150
• Storage Temp.: Store at RT
• Solubility.: H2O: soluble
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 151

Purity/Quality:

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

Guvacine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC(=C1)C(=O)O
• Uses: Guvacine Hydrochloride is a GABA uptake inhibitor (hGABA T-1, rGABA T-2, hGABA T-3 and hBGT-1) (1,2,3). Gamma-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian brain (4). Guvacine Hydrochloride may be useful for treating neuropsychiatric disorders.

Technology Process of Guvacine

There total 17 articles about Guvacine 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: 72.0%

norarecoline (495-19-2) → guvacine (498-96-4)

Guidance literature:

In water; for 3h; Reflux;

DOI:10.1002/anie.201301341

Reference yield:

1-benzoyl-4-hydroxy-piperidine-3-carboxylic acid ethyl ester (5435-00-7) → guvacine (498-96-4)

Guidance literature:

With hydrogenchloride; at 180 - 200 ℃;

DOI:10.1021/ja01210a040

Reference yield:

1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide (17210-51-4) → guvacine (498-96-4)

Guidance literature:

With barium dihydroxide; In water; at 40 ℃; for 0.5h;

upstream raw materials:

nicotinic acid

3-pyridinecarboxylic acid ethyl ester

1-benzoyl-4-hydroxy-piperidine-3-carboxylic acid ethyl ester

1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrobromide

Downstream raw materials:

(R)-nipecotic acid

(R)-tert-butyl 3-(phenylcarbamoyl)piperidine-1-carboxylate

5-Bromomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Song, Song,Zhu, Shou-Fei,Pu, Liu-Yang,Zhou, Qi-Lin. "Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids". . p. 6072 - 6075. Retrieved 2013/07/05.
• 2、 Wolf-Pflugmann,Lambrecht,Wess,Mutschler. "Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester". . p. 539 - 544. Retrieved 2007/10/02.