Product Introduction
| HEXAMETHONIUM BROMIDE Basic information |
| Product Name: | HEXAMETHONIUM BROMIDE |
| Synonyms: | gangliostat;hexamethioniumbromide;hexamethylenebis(trimethyl-ammoniudibromide;hexameton;hexoniumdibromide;simpatoblock;Methobromine;Hexamethonium bromide,Hexane-1,6-bis(trimethylammonium bromide), N,N,N,N′,N′,N′-Hexamethylhexamethylenediammonium dibromide |
| CAS: | 55-97-0 |
| MF: | C12H30Br2N2 |
| MW: | 362.19 |
| EINECS: | 200-249-7 |
| Product Categories: | Ammonium Bromides (Quaternary);Quaternary Ammonium Compounds |
| Mol File: | 55-97-0.mol |
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| HEXAMETHONIUM BROMIDE Chemical Properties |
| 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 |
| Merck | 14,4688 |
| BRN | 3715749 |
| InChIKey | FAPSXSAPXXJTOU-UHFFFAOYSA-L |
| 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 Information |
| Safety Statements | 22-24/25 |
| WGK Germany | 2 |
| RTECS | BQ8575000 |
| TSCA | Yes |
| HS Code | 29239000 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| HEXAMETHONIUM BROMIDE Usage And Synthesis |
| Description | Hexamethonium is a peripherally-acting nondepolarizing neuromuscular blocking agent that acts as an antagonist of nicotinic acetylcholine receptors (nAChRs). It decreases acetylcholine release induced by carbamoylcholine in isolated cat superior cervical ganglion when used at concentrations of 27.4 and 54.8 μg/ml. It also decreases mean arterial pressure in unanesthetized rats when administered at a dose of 40 mg/kg. Intraventricular administration of hexamethonium (18 ng, i.c.v.) induces signs of nicotine abstinence, including shaking, writhing, and chewing in nicotine-dependent rats. 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. |
| HEXAMETHONIUM BROMIDE Preparation Products And Raw materials |
| Raw materials | Ethanol-->Ethyl acetate-->Hydrogen bromide-->Calcium hydroxide-->Trimethylamine-->1,6-Hexanediol-->Trimethylamine hydrochloride-->1,6-Dibromohexane-->Dimethyl sulfate-->Sodium hydroxide-->Hexamethylenediamine |
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