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H0879

Sigma-Aldrich

Hexamethonium bromide

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Synonym(s):
Hexane-1,6-bis(trimethylammonium bromide), N,N,N,N′,N′,N′-Hexamethylhexamethylenediammonium dibromide
Linear Formula:
(CH3)3N(Br)(CH2)6N(Br)(CH3)3
CAS Number:
55-97-0
Molecular Weight:
362.19
Beilstein:
3715749
EC Number:
200-249-7
MDL number:
MFCD00011787
PubChem Substance ID:
24278459
NACRES:
NA.77

Quality Level

200

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

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 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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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
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