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M1559

Sigma-Aldrich

Moxonidine hydrochloride

≥98%

Synonym(s):

4-Chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)aminopyrimidine hydrochloride, BDF-5895

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About This Item

Empirical Formula (Hill Notation):
C9H12ClN5O · HCl
CAS Number:
75438-58-3
Molecular Weight:
278.14
MDL number:
MFCD06795643
UNSPSC Code:
12352200
PubChem Substance ID:
24278537
NACRES:
NA.77

Quality Level

100

Assay

≥98%

originator

Solvay

SMILES string

Cl.COc1nc(C)nc(Cl)c1NC2=NCCN2

InChI

1S/C9H12ClN5O.ClH/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9;/h3-4H2,1-2H3,(H2,11,12,15);1H

InChI key

ZZPAWQYZQVUVHX-UHFFFAOYSA-N

Gene Information

human ... ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , NISCH(11188)

Application

Moxonidine hydrochloride has been used:
  • as a standard to study its blood-brain barrier (BBB) permeability in porcine brain lipid extract by parallel artificial membrane permeability assay (PAMPA) method
  • as a standard to study the chromatographic behavior and lipophilicity by reversed-phase thin-layer chromatography (RP-TLC)
  • as an imidazoline I1 receptor agonist to study its effects on excitatory inputs in airway vagal preganglionic neuron (AVPN)

Biochem/physiol Actions

Moxonidine is a selective high-affinity imidazoline I1-receptor agonist and a selectively low-affinity α2-adrenoceptor agonist. It exhibits anti-hypertensive properties by reducing blood pressure efficiently. Moxonidine also exhibits spinal analgesic activity through the α2C-adrenoceptor component.

Features and Benefits

This compound is featured on the Imidazoline Binding Sites page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Solvay. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using RP-TLC
Mohamed S, et al.
Journal of Liquid Chromatography and Related Technologies, 37(20), 2829-2845 (2014)
Xujiao Zhou et al.
Brain research, 1732, 146695-146695 (2020-02-03)
As an imidazoline I1 receptor agonist with very weak binding affinity for α2-adrenoceptors, moxonidine is commonly used in the treatment of hypertension. Moxonidine also has been implicated to act centrally to reduce airway vagal outflow. However, it is unknown at
Jelica Vucicevic et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 68, 94-105 (2014-12-30)
Imidazoline receptor ligands are a numerous family of biologically active compounds known to produce central hypotensive effect by interaction with both α2-adrenoreceptors (α2-AR) and imidazoline receptors (IRs). Recent hypotheses connect those ligands with several neurological disorders. Therefore some IRs ligands
Caroline Fenton et al.
Drugs, 66(4), 477-496 (2006-04-07)
Moxonidine (Physiotens, Moxon, Cynt) is an orally administered imidazoline compound with selective agonist activity at imidazoline I1 receptors and only minor activity at alpha2-adrenoceptors. Moxonidine acts centrally to reduce peripheral sympathetic activity, thus decreasing peripheral vascular resistance. In patients with
Laura S Stone et al.
Annals of the New York Academy of Sciences, 1009, 378-385 (2004-03-19)
Moxonidine is a mixed alpha(2)-adrenergic and imidazoline receptor agonist with an improved side effect profile compared to clonidine. Intrathecal (i.t.) moxonidine has been found to possess analgesic activity that, in contrast to the majority of alpha(2)-adrenoceptor (alpha(2)AR) agonists, does not
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