55-97-0 Usage
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 ratsas a nicotinic receptor antagonist to study its effects on antigen-induced arthritis (AIA) progression in miceas 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.
Check Digit Verification of cas no
The CAS Registry Mumber 55-97-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 55-97:
(4*5)+(3*5)+(2*9)+(1*7)=60
60 % 10 = 0
So 55-97-0 is a valid CAS Registry Number.
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
55-97-0Relevant articles and documents
Solid-state synthesis of mixed trihalides via reversible absorption of dihalogens by non porous onium salts
Meazza, Lorenzo,Marti-Rujas, Javier,Terraneo, Giancarlo,Castiglioni, Chiara,Milani, Alberto,Pilati, Tullio,Metrangolo, Pierangelo,Resnati, Giuseppe
, p. 4427 - 4435 (2011)
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.
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Burger,A.,Bedford,G.R.
, p. 402 - 405 (1963)
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Double-quaternary ammonium salt compound, synthetic method and use thereof
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Paragraph 0059; 0060; 0061, (2017/12/27)
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.
