| Identification | More | [Name]
HEXAMETHONIUM BROMIDE | [CAS]
55-97-0 | [Synonyms]
HEXAMETHONIUM BROMIDE
HEXAMETHONIUM DIBROMIDE
HEXAMETHYLENEBIS(TRIMETHYLAMMONIUM BROMIDE)
HEXANE-1,6-BIS(TRIMETHYLAMMONIUM BROMIDE)
N,N,N,N',N',N'-HEXAMETHYLHEXAMETHYLENEDIAMMONIUM DIBROMIDE
6-hexanediaminium,n,n,n,n’,n’,n’-hexamethyl-dibromide
alpha,omega-bis(trimethylammonium)hexanedibromide
esametina
gangliostat
hexamethioniumbromide
hexamethylenebis(trimethyl-ammoniudibromide
hexameton
hexoniumdibromide
simpatoblock
vegolysen
vegolysin
Hexane-1,6-bis(trimethylammonium bromide), N,N,N,Nμ,Nμ,Nμ-Hexamethylhexamethylenediammonium dibromide
Hexamethonium bromide ,98%
HEXAMETHONIUM BROMIDE HYDRATE, 98+%
Methobromine | [EINECS(EC#)]
200-249-7 | [Molecular Formula]
C12H30Br2N2 | [MDL Number]
MFCD00011787 | [Molecular Weight]
362.19 | [MOL File]
55-97-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystalline powder and agglomerates | [Melting point ]
~285 °C (dec.)
| [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Water (Slightly) | [form ]
Crystalline Powder and Agglomerates | [color ]
White | [PH]
pH (20g/l, 25℃) : 4.5～6.5 | [Water Solubility ]
H2O: 100mg/mL | [Detection Methods]
Silver Method | [Merck ]
4688 | [BRN ]
3715749 | [InChI]
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 | [InChIKey]
FAPSXSAPXXJTOU-UHFFFAOYSA-L | [SMILES]
C(CCCCC[N+](C)(C)C)[N+](C)(C)C.[Br-].[Br-] | [CAS DataBase Reference]
55-97-0(CAS DataBase Reference) | [EPA Substance Registry System]
1,6-Hexanediaminium, N1,N1,N1,N6,N6,N6-hexamethyl-, bromide (1:2) (55-97-0) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [RTECS ]
BQ8575000
| [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29239000 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
Hexamethonium is a peripherally-acting nondepolarizing neuromuscular blocking agent that acts as an antagonist of nicotinic acetylcholine receptors (nAChRs).1,2 It decreases acetylcholine release induced by carbamoylcholine (Item No. 14486) in isolated cat superior cervical ganglion when used at concentrations of 27.4 and 54.8 μg/ml.3 It also decreases mean arterial pressure in unanesthetized rats when administered at a dose of 40 mg/kg.4 Intraventricular administration of hexamethonium (18 ng, i.c.v.) induces signs of nicotine abstinence, including shaking, writhing, and chewing in nicotine-dependent rats.5 Formulations containing hexamethonium were previously used in the treatment of hypertension. | [Chemical Properties]
White crystalline powder and agglomerates | [Originator]
Bistrium,Squibb,US,1951 | [Uses]
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
| [Manufacturing Process]
Hexamethylene diamine (116 g), sodium carbonate (466 g), and water (800
ml) were heated to 60°C, and dimethyl sulfate (830 g) added with stirring
over 1% hours keeping the temperature below 90°C. The reaction mixture
was then stirred at 90°C for 2 hours, then cooled to 20°C, acetone (1,200 ml)
added and the whole cooled to 0°C.
The solid formed was removed by filtration and washed with acetone (150
ml). Filtrate and washings were diluted with water to 4 liters and heated to
60°C under reflux. To this was added a solution prepared from embonic acid
(388 g), sodium hydroxide (80 g) and water (5 liters), the whole refluxed for
10 minutes and thereafter allowed to cool overnight.
The resultant embonate (530 g) was filtered off, washed twice with a solution
of acetone (75 ml) in water (425 ml), and dried at 100°C to give an
amorphous yellow powder, MP 290°C to 291°C (with decomp.). 588 g of the
embonate was dissolved in boiling water (4 liters).
Hydrobromic acid 50% w/w (325 g) diluted with water (2 liters) was added
slowly at the boil and the precipitated embonic acid removed by filtering hot
and washing twice with hot water (1 liter). The filtrate and washings were
evaporated to dryness in a steam pan and the residue recrystallized from
ethyl alcohol (1,200 ml), to yield the dibromide (320 g). | [Therapeutic Function]
Antihypertensive | [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. | [References]
[1] J A GOSLING T C L. Uptake and distribution of some quaternary ammonium compounds in the central nervous system of the rat.[J]. Journal of Pharmacology and Experimental Therapeutics, 1969, 167 1: 56-62.
[2] D N MCKINSTRY G B K. Effects of drugs on acetylcholine release from the cat superior cervical ganglion by carbachol and by preganglionic stimulation.[J]. Journal of Pharmacology and Experimental Therapeutics, 1967, 157 2: 328-336.
[3] YASUHIRO NISHIDA. Long-term blood pressure control: is there a set-point in the brain?[J]. Journal of Physiological Sciences, 2012, 62 3: 147-161. DOI: 10.1007/s12576-012-0192-0
[4] DAVID H MALIN . Nicotine Abstinence Syndrome Precipitated by Central But Not Peripheral Hexamethonium[J]. Pharmacology Biochemistry and Behavior, 1997, 58 3: Pages 695-699. DOI: 10.1016/s0091-3057(97)90006-x |
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