H0879
Hexamethonium bromide
nAChR antagonist
Synonym(s):
Hexane-1,6-bis(trimethylammonium bromide), N,N,N,N′,N′,N′-Hexamethylhexamethylenediammonium dibromide
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About This Item
Linear Formula:
(CH3)3N(Br)(CH2)6N(Br)(CH3)3
CAS Number:
Molecular Weight:
362.19
Beilstein:
3715749
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
Hexamethonium bromide,
Quality Level
mp
282-285 °C (dec.)
SMILES string
[Br-].[Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C
InChI
1S/C12H30N2.2BrH/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
FAPSXSAPXXJTOU-UHFFFAOYSA-L
Gene Information
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Application
Hexamethonium bromide has been used:
- as an autonomic ganglia-blocking agent to study its effects on whisker movement in rats
- as a nicotinic receptor antagonist to study its effects on antigen-induced arthritis (AIA) progression in mice
- as a non-selective ganglionic nicotinic acetylcholine receptor (nAChR) antagonist to study its effects on cytisine-induced autonomic cardiovascular responses in mice
Biochem/physiol Actions
Hexamethonium bromide is a nicotinic acetylcholine receptor (nAChR) antagonist. It preferentially blocks nicotinic receptors at autonomic ganglia. It can cross the blood-brain barrier only at high doses.
Features and Benefits
This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Piyali Dasgupta et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(16), 6332-6337 (2006-04-08)
Non-small cell lung cancer (NSCLC) demonstrates a strong etiologic association with smoking. Although nicotine is not carcinogenic, it can induce cell proliferation and angiogenesis and suppress apoptosis induced by certain agents. Here we show that nicotine inhibits apoptosis induced by
Yi-Fan Li et al.
Autonomic neuroscience : basic & clinical, 154(1-2), 14-19 (2009-11-06)
Nicotinic cholinergic receptors mediate autonomic transmission at ganglia. However, whether different subtypes of nicotinic cholinergic receptors expressed in autonomic ganglia elicit distinct roles in mediating sympathetic and parasympathetic regulations remain to be defined. In this study, we observed that different
Alexandre Kanashiro et al.
Basic & clinical pharmacology & toxicology, 119(5), 453-457 (2016-04-22)
The cholinergic anti-inflammatory pathway (CAP) is a complex neuroimmune mechanism triggered by the central nervous system to regulate peripheral inflammatory responses. Understanding the role of CAP in the pathogenesis of rheumatoid arthritis (RA) could help develop new therapeutic strategies for
James T Heaton et al.
Neuroscience, 265, 9-20 (2014-02-01)
Vibrissal whisking is often employed to track facial nerve regeneration in rats; however, we have observed similar degrees of whisking recovery after facial nerve transection with or without repair. We hypothesized that the source of non-facial nerve-mediated whisker movement after
Kamila Shakarchi et al.
The Journal of experimental biology, 216(Pt 5), 869-880 (2012-11-17)
The chemosensory roles of gill neuroepithelial cells (NECs) in mediating the hyperventilatory response to hypoxia are not clearly defined in fish. While serotonin (5-HT) is the predominant neurotransmitter in O(2)-sensitive gill NECs, acetylcholine (ACh) plays a more prominent role in
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