Methobromide

B. HAUCI4, separates as an oil, but solidifies on standing and may be recrystallised from water containing hydrochloric acid. The crystals melt at 137-9° or below 100° when heated under water. This salt and the picrate, rectangular plates, m.p. 175-6°, are well adapted for the identification of the alkaloid. The methobromide, m.p. 223-5°, and the inethonitrate, m.p. 166-8°, are now both used in medicine. 

Phenylglycollyltropeine Mandelyltropeine, homatropine), CigHjiOjN. This is largely used as a substitute for atropine. It crystallises in prisms, m.p. 95-5-98-5°. The hydrobromide, the salt usually employed in medicine, is a crystalline powder, m.p. 217-8° (dec.) the hydrochloride, m.p. 224-5°, and the salicylate are also used. All tl ee are freely soluble in water. The methobromide has m.p. 192-6°. The aurichloride, B. HAUCI4, forms prisms and is sparingly soluble in water. Homatropine, unlike atropine, does not give the Vitali colour reaction (p. 70). Its mydriatic effect is more rapid and transient than that of atropine. 

Of the proximate derivatives of atropine, the methobromide and the methonitrate are in use for much the same purposes as atropine, but the methonitrate has received special attention for the treatment of pyloric stenosis. opoAtropine has been found by Mancini to retain the same type of action as atropine but to be less potent in peripheral and more active in central nervous action. ... 

Most of the esters were given as hydrochlorides, but where methobromides were used to ensure solubility they were in some cases less irritant and at least as active as the usual salt. 

Hydrogenation of i-butyl nicotinate methobromide, followed by hydrolysis of the 1-methyl-3-tert-butoxycarbonyl-1,4,5,6-tetrahydro-pyridine product (205) in the presence of indole affords, on decarboxylation, the -substituted derivative (206) (325). The formation of... 

Preparation of the Methyl Bromide To the acetone solution of the free base was added an acetone solution, containing an excess of methyl bromide. Within a few minutes the methobromide started to crystallize. The mixture was allowed to stand for several hours. The crystallized solid was filtered, and additional product was obtained by evaporation of the filtrate. The yield was nearly quantitative. After recrystallization from acetone, the product melted at 329°C. 

Benziloyloxy-1-azabicyclo[2.2.2] octane methobromide was prepared by adding 20 cc of a 30% solution of methyl bromide in ether to a solution of 2.5 g of 3-benziloyloxy-1-azabicyclo[2.2.2] octane in 20 cc of chloroform. After standing for 3 hours at room temperature and 15 hours at -i-5°C, a crystalline precipitate had formed. This was filtered off and recrystallized from a mixture of methanol, acetone, and ether prisms melting at 240° to 241°C. 

Preparation of 4-Phenyl-4-Cyano-N-Methyl Azacydoheptane Methobromide A 0.1 M nitrobenzene solution of 1-dimethylamino-3-cyano-3-phenyl-6-bromohexane was kept at 100°C for 1 hour whereby the quaternary salt precipitated out MP 246 to 247 C. 

Chemical Name 3-[ hydroxydiphenylacetyl)oxy]-1,1-dimethylpiperidinium bromide Common Name N-methyl-3-piperidyl benzilate methobromide... 

Therapeutic Function Anticholinergic bronchodilator Chemical Name (-)-N-Ethylnorscopolamine methobromide... 

Methyl bromide (17 grams) was added to a solution of the bis-piperidinodiacetate (4 grams) in methylene chloride (10 ml) and the resulting solution allowed to stand at room temperature for 4 days. The solution was evaporated to dryness, the residue triturated with ether, and filtered to give the bis-methobromide (5.2 grams), MP 206°C. Recrystallization from acetone-methylene chloride gave material MP 214°-217°C. 

Chemical Name N-Methyl-4-piperidylbenzilate methobromide Common Name —... 

N-methyl-4-piperidyl benzilate methobromide To a suspension of 0.15 mol of freshly prepared silver bromide in 300 ml of anhydrous methanol is added a solution of 0.1 mol of quaternary iodide obtained as above. The mixture is stirred and refluxed for several hours after which time transhalogenation is complete. The mixture is cooled, the insoluble silver... 

The hydrochloride may then be converted to the methobromide by reaction with methyl bromide. 

Common Name Diisopropylaminoethyl xanthene-9-carboxylate methobromide... 

The reaction mixture is chilled, diluted with anhydrous ether and the quaternary salt thus precipitated is collected on a filter and washed with dry ether and then with butanone. (3-Diisopropylaminoethyl xanthene-9-carboxylate methobromide thus obtained melts at 152°-153°C. After recrystallization from isopropanol it melts at 157°-155°C. 

Benzyl cyanide is first reacted with 2-butylbromide in the presence of sodium amide to give 2-phenyl-3-methylvaleronitrile which is hydrolyzed by sulfuric acid to give 3-methyl-2-phenyl-pentanoic acid. 24 g of 2-phenyl-3-methyl-pentanoic acid are heated for one hour at 175° to 185°C with 30 g of 2-diethylaminoethanol and 0.5 g of sodium methylate. The excess diethyl-aminoethanol is removed in vacuo, the residue is dissolved in 300 cc of 2 N-acetic acid, the acid solution is shaken with ether and made alkaline with concentrated potassium carbonate solution and ice. The ether solution Is washed with water, dried with sodium sulfate and evaporated. The residue is distilled under high vacuum, yielding 20 to 21 g of the basic ester (60% of the theoretical) is obtained, the ester boiling at 98° to 100°C at a pressure of 0.03 mm. The hydrochloride of the ester melts at 112° to 113°C and the methobromide at 100° to 101°C. 

C27H29C105 83880-65-3) see Mometasone furoate chloroglyoxylic acid ethyl ester (C4H5CIO3 4755-77-5) see Oxitefonium bromide Penthienate methobromide Tiaprofenic acid... 

CjHijBrMg 33240-34-5) see Cycrimine Glycopyrronium bromide Ketamine Penthienate methobromide... 

Testosterone cypionate cyclopentyl-2-thienylglycolic acid (C11H14O3S 3899-50-1) see Penthienate methobromide cyclopentyl-2-thienylglycolic acid 2-diethylaminoethyl ester... 

C4H4S 110-02-1). see Clopidogrel hydrogensulfate Oxitefonium bromide Penthienate methobromide Suprofen 2-Thiophenecarboxylic acid Tiaprofenic acid Ticlopidine Tiemonium iodide Tienilic acid... 

The diphenolic protoberberine methobromide 285 derived from 283 was refluxed in aqueous ethanolic sodium hydroxide for 12 hr to furnish the quinomethide 287 in 92% yield (Scheme 50). Compound 287 was treated with dimethyl sulfoxide to give rise to the desired diphenolic ochotensimine analog 288 through enolization (150,151). The presence of the phenolic hydroxyl group is essential in this rearrangement because the benzyl ether (284) was recovered unchanged under the same alkaline conditions. 

Antirhine methobromide (12) has been isolated from Strychnos camptoneura Gilg and Busse (20) however, it is not certain that this is the naturally occurring form of the alkaloid. In view of H-NMR evidence, a orientation was suggested for the Ab-methyl group of 12. 

Guay DRP (2009) Methylnaltrexone methobromide The first peripherally active, centrally inactive opioid receptor-antagonist. Consult Pharm 24 210-226. 

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