55-97-0

Usage

Uses

Used in Autonomic Ganglia Research:
Hexamethonium bromide is used as an autonomic ganglia-blocking agent for studying its effects on whisker movement in rats. This application aids in understanding the role of autonomic ganglia in motor control and neurological functions.
Used in Nicotinic Receptor Research:
In the field of nicotinic receptor research, hexamethonium bromide serves as a nicotinic receptor antagonist, enabling the study of its impact on antigen-induced arthritis (AIA) progression in mice. This helps researchers to explore the potential therapeutic effects of hexamethonium bromide in managing inflammatory conditions.
Used in Cardiovascular Response Studies:
Hexamethonium bromide is utilized as a non-selective ganglionic nicotinic acetylcholine receptor (nAChR) antagonist in studies examining its effects on cytisine-induced autonomic cardiovascular responses in mice. This application is crucial for investigating the drug's influence on the cardiovascular system and its potential use in treating related conditions.

Originator

Bistrium,Squibb,US,1951

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.

InChI:InChI=1/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

Upstream product

• 71655-17-9 (E)-3-hexen-1,6-diol 
• 18715-38-3 trans-1,4-dicyano-2-butene 
• 629-03-8 1 ,6-dibromohexane 
• 75-50-3 trimethylamine 
• 57042-08-7 Diethyl trans-hex-3-enedioate 
• 59533-63-0 1,6-dibromo-trans-3-hexene 
• 66967-77-9 trans-1.6-Bis-trimethylammonio-hexen-⁽³⁾-dibromid 

Relevant academic research and scientific papers

Solid-state synthesis of mixed trihalides via reversible absorption of dihalogens by non porous onium salts

1,6-Bis(trimethylammonium)hexane bis(trihalides) and mixed bis(trihalides) have been synthesized by treating the corresponding dihydrated halides with molecular dihalogens under gas-solid and solution conditions. Despite the starting halides being non-porous, the trihalide syntheses occur homogeneously, in quantitative yields, and reversibly. In all cases halogen bond prevails over hydrogen bond, dihalogens substitute for the hydration water of starting halide anions and trihalides are formed. The stability of the obtained trihalides is mainly due to cooperative halogen bond and cation templation effect. Hexamethonium halides are proven effective solids for the clathration and storage of molecular dihalogens. While the starting salts are not isostructural, all the formed trihalides and mixed trihalides are isostructural.

Microwave-assisted synthesis of a thermally stable Zn-containing aluminophosphate with ERI-zeotype structure templated by diquaternary alkylammonium

Microwave-assisted hydrothermal synthesis of a Zn-containing aluminophosphate with ERI-zeotype structure, was successfully prepared by using N,N,N,N′,N′,N′-hexamethyl-1,6-hexanediammonium (Me6-diquat-6) as the template. The as-synthesized zeolite possesses high thermal stability, large surface area and weak and medium acid sites, which will be potentially interesting for applications in adsorption and catalysis. This journal is

Preparation method of biquaternary ammonium salt compound

The invention belongs to the field of chemistry, and provides a preparation method of a biquaternary ammonium salt compound. The preparation method comprises the following steps: by taking dibromoalkane and a trimethylamine aqueous solution as raw materials and ethanol as a solvent, reacting in a homogeneous system at 25-80 DEG C for 4-48 hours, and after the reaction is finished, distilling and washing to obtain a pure product. The reaction is simple and efficient, the cost is low, and the use of trimethylamine gas and other high-safety-risk raw materials and trimethylamine methanol solution and other high-economic-cost raw materials can be avoided in the preparation process; the defects of heterogeneous reaction and low conversion rate caused by independently using a trimethylamine aqueous solution and dibromoalkane as reaction raw materials are overcome; high-risk organic solvents such as diethyl ether are not used in the post-treatment process, and all the used organic solvents can be recycled.

Double-quaternary ammonium salt compound, synthetic method and use thereof

The invention provides an organic diammonium compound, as well as a synthetic method and use thereof. The organic diammonium compound is n-alkyl hexamethyl ammonium dibromide adopting a Bola type structure, and the carbon number in dienal bases is a positive even number. The synthetic method of the organic diammonium compound comprises the following steps of: step I, mixing a trimethylamine solution and 1, n- dibrom X alkane and performing a reaction on the mixed trimethylamine solution and the mixed 1, n- dibrom X alkane so as to form the n-alkyl hexamethyl ammonium dibromide, wherein n is a numerical value same as X and is a positive even number; and step II, separating and purifying the n-alkyl hexamethyl ammonium dibromide so as to obtain the finished product of the n-alkyl hexamethyl ammonium dibromide. The organic diammonium compound has the functions of scale removal, oil displacement, adsorption and the like, can be used as an organic diammonium compound, a disincrustant and an oil displacement agent adsorbent, and is simple in the synthetic method and easy to operate.

The bisnaphthalimides as new active lead compounds against Plasmodium falciparum

The bisquaternary bisnaphthalimides are a versatile class of compounds being active against the malaria parasite Plasmodium falciparum in the lower nanomolar range of concentration combined with no cytotoxicity. The series of compounds is designed as choline analogues and interfering agents of the phosphatidylcholine biosynthesis. The qualitative analysis of the structure-activity relationships (SAR) revealed the importance of a long methylene middle chain of at least 8 methylene groups between the two bisquaternary naphthalimides or a monoquaternary naphthalimide consisting of a long alkyl chain attached to the positively charged nitrogen atom. Since the SARs are different from reported biscationic antimalarial drugs the mode of action remains to be elucidated.

Porous crystalline material (zeolite ITQ-24), preparation method thereof and use of same in the catalytic conversion of organic compounds

The invention relates to a porous crystalline material (ITQ-24), the preparation method thereof and the use of same in the catalytic conversion of organic compounds. More specifically, the invention relates to a synthetic porous crystalline material which is characterised in that it is formed by tetrahedrally coordinated atoms which are interconnected by means of oxygens. Said material, which comprises a unit cell containing 56 tetrahedrally coordinated atoms, is known as ITQ-24. Moreover, in the calcined anhydrous state, the material has chemical formula nM1/pXO2: YO2, wherein: X is at least one trivalent element, Y is at least one tetravalent element, n is between 0 and 0.2 and M is at least one charge compensation cation in oxidation state p.