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Merck
CN

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

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About This Item

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

Key Documents

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Product Name

Hexamethonium chloride, solid (hygroscopic)

InChI key

PYIHTIJNCRKDBV-UHFFFAOYSA-L

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

SMILES string

[Cl-].[Cl-].C[N+](C)(C)CCCCCC[N+](C)(C)C

form

solid (hygroscopic)

color

white

solubility

H2O: soluble
ethanol: soluble

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)

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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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000501659
0000501658
0000501658
0000501659
0000477074

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Julia Yuen Hang Liu et al.
American journal of physiology. Gastrointestinal and liver physiology, 319(1), G97-G107 (2020-06-02)
The effect of acetylcholine (ACh) on pacemaking and spontaneous contractions in the gastrointestinal tract is not well characterized. The current study aims to profile the effect of several muscarinic and nicotinic receptor agonists and antagonists on pacemaker potentials in the
Animal Models of Cognitive Impairment, 381-394 (2006)
Viscerofugal neurons recorded from guinea-pig colonic nerves after organ culture
Hibberd TJ, et al.
Neurogastroenterology and Motility, 24(11), 1041-e548-1041-e548 (2012)
Pharmacology and Therapeutics for Dentistry, 138-138 (2010)
Abimael González-Hernández et al.
ACS chemical neuroscience, 10(7), 3173-3182 (2019-01-30)
Calcitonin gene-related peptide (α-CGRP) released from perivascular sensory nerves induces decreases in diastolic blood pressure (DBP). Experimentally, this can be shown by spinal thoracic (T9-T12) electrical stimulation of these afferent fibers. Because ergotamine inhibits these neurogenic vascular responses and displays
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