H2138

Hexamethonium chloride

solid (hygroscopic)

• Synonym(s): Hexamethonium dichloride, N,N,N,N′,N′,N′-Hexamethyl-1,6-hexanediaminium dichloride, N,N,N,N′,N′,N′-Hexamethylhexamethylenediammonium dichloride
• Linear Formula: (CH₃)₃N(Cl)(CH₂)₆N(Cl)(CH₃)₃
• CAS Number: 60-25-3
• Molecular Weight: 273.29
• Beilstein/REAXYS Number: 3714806
• EC Number: 200-465-1
• MDL number: MFCD00031563
• UNSPSC Code: 12352200
• PubChem Substance ID: 24277842
• NACRES: NA.77

Properties

• form: solid (hygroscopic)
• color: white
• solubility: H₂O: soluble; ethanol: soluble
• SMILES string: [Cl-].[Cl-].C[N+](C)(C)CCCCCC[N+](C)(C)C
• InChI: 1S/C12H30N2.2ClH/c1-13(2,3)11-9-7-8-10-12-14(4,5)6;;/h7-12H2,1-6H3;2*1H/q+2;;/p-2
• InChI key: PYIHTIJNCRKDBV-UHFFFAOYSA-L
• Gene Information: human ... CHRNA1(1134), CHRNA10(57053), CHRNA2(1135), CHRNA3(1136), CHRNA4(1137), CHRNA5(1138), CHRNA6(8973), CHRNA7(1139), CHRNA9(55584), CHRNB1(1140), CHRNB2(1141), CHRNB3(1142), CHRNB4(1143)

Description

General description

Nicotinic acetylcholine receptor (nAChR) forms a ligand-gated ion channel made up of four different subunits. Each subunit contains an extracellular amino-terminal domain (hydrophilic) and carboxylic terminal domain and four transmembrane domains. nAChR is an allosteric and transmembrane protein localized to the neuromuscular junction.

Application

Hexamethonium chloride has been used to block the responses of nicotinic receptors towards it agonists. It has also been used to study the mechanosensitivity of viscerofugal neurons.

Biochem/physiol Actions

Hexamethonium chloride preferentially blocks nicotinic receptors at autonomic ganglia, crosses blood-brain barrier only at high doses. Nicotinic acetylcholine receptor (nAChR) is responsible for cognitive functions. Blocking this receptor results in cognitive impairment. nAChR antagonist is used to study the effect of loss of receptor function. Hexamethonium has a peripheral action over blocking the nAChR.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)