Moxonidine

Base Information

• Chemical Name: Moxonidine
• CAS No.: 75438-57-2
• Molecular Formula: C9H12ClN5O
• Molecular Weight: 241.68
• European Community (EC) Number: 629-833-3
• UNII: CC6X0L40GW
• DSSTox Substance ID: DTXSID5045170
• Nikkaji Number: J32.886C
• Wikipedia: Moxonidine
• Wikidata: Q419944
• NCI Thesaurus Code: C87629
• Pharos Ligand ID: 5F27N1Y5NK8X
• Metabolomics Workbench ID: 49643
• ChEMBL ID: CHEMBL19236
• Mol file: 75438-57-2.mol

Synonyms:4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine;BE 5895;BE-5895;Cynt;Moxon;moxonidin;moxonidine;Normatens;Physiotens

Chemical Property of Moxonidine

Chemical Property:

• Appearance/Colour: crystal
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Melting Point: 217-219 °C
• Refractive Index: 1.68
• Boiling Point: 364.7 °C at 760 mmHg
• PKA: 7.11±0.10(Predicted)
• Flash Point: 174.3 °C
• PSA: 71.43000
• Density: 1.52 g/cm³
• LogP: 0.65550
• Storage Temp.: Desiccate at +4°C
• Solubility.: Very slightly soluble in water, sparingly soluble in methanol, slightly soluble in methylene chloride, very slightly soluble in acetonitrile.
• Water Solubility.: 800.3mg/L(temperature not stated)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 241.0730377
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

99%, ^*data from raw suppliers

Moxonidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=C(C(=N1)Cl)NC2=NCCN2)OC
• Recent ClinicalTrials: Autonomic Determinants of POTS - Pilot1
• Recent EU Clinical Trials: A randomized, placebo-controlled, double blind, 4-period, cross-over trial, to study blood pressure lowering effects of losartan, Moxonidine and Low sodium diet in former pre-eclamptic women
• Description: Moxonidine, also known as Physiotens, is a highly selective imidazoline receptor agonist-Ⅰ by excitement ventrolateral medulla nucleus (RVLM)-Ⅰ type imidazoline receptor in the peripheral sympathetic nerve activity decreased. This receptor subtype is found in both the rostral ventro-lateral pressor and ventromedial depressor areas of the medulla oblongata. Moxonidine therefore causes a decrease in sympathetic nervous system activity and, therefore, a decrease in blood pressure. It is a new type of antihypertensive drug, commonly used in the treatment of essential hypertension. Compared to the older central-acting antihypertensives, moxonidine binds with much greater affinity to the imidazoline I1-receptor than to the α2-receptor. In contrast, clonidine binds to both receptors with equal affinity. It may have a role when thiazides, beta-blockers, ACE inhibitors and calcium channel blockers are not appropriate or have failed to control blood pressure. Moxonidine, which is structurally related to clonidine, is a new centrally acting antihypertensive that acts as a stronger agonist at imidazole receptors and a weaker agonist at α2-adrenergic receptors than clonidine. It is also reported to have less side effects and a much reduced potential to produce a rebound in blood pressure on withdrawal. Clinically, moxonidine appears to have comparable antihypertensive efficacy with the ACE inhibitors and calcium antagonists.
• Uses: Moxonidine is an antihypertensive agent. Antihypertensive;Imidazoline receptor agonist
• Clinical Use: Antihypertensive agent (centrally acting agonist at I1 receptor, imidazoline and alpha2 adrenoceptors)
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Moxonidine

There total 17 articles about Moxonidine 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: 94.0%

mono-Moxonidine oxalate (287099-40-5) → 4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine (352457-35-3) + 4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine (75439-01-9) + moxonidine (75438-57-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 1h; pH=10 - 11; Product distribution / selectivity;

Reference yield: 90.7%

methanol (67-56-1) + 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine (75438-54-9) → 4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine (75439-01-9) + moxonidine (75438-57-2)

Guidance literature:

With potassium carbonate; at 65 ℃; for 3h; Product distribution / selectivity;

Reference yield: 88.3%

methanol (67-56-1) + 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine (75438-54-9) → 4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine (352457-35-3) + 4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine (75439-01-9) + moxonidine (75438-57-2)

Guidance literature:

With sodium hydrogencarbonate; In water; at 65 ℃; for 6h; Product distribution / selectivity;

upstream raw materials:

4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine

sodium methylate

methanol

mono-Moxonidine oxalate

Downstream raw materials:

4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

mono-Moxonidine oxalate

mono-Moxonidine formate

4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine

Refernces

• 1、 -. "SYNTHESIS OF SUBSTITUTED AMINOPYRIMIDINES". Page/Page column 17; 18. . Retrieved 2015/02/19.
• 2、 -. "Method by means of phase transfer catalysis". Paragraph 0080. . Retrieved 2014/06/24.