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H2138

Sigma-Aldrich

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
Beilstein/REAXYS Number:
3714806
EC Number:
200-465-1
MDL number:
MFCD00031563
UNSPSC Code:
12352200
PubChem Substance ID:
24277842
NACRES:
NA.77

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)

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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.

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)

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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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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