Tubocurarine Iodide

Smedslund, T.H. U.S. Patent 2,581,050 January 1,1952 assigned to A.B. Centrallabora-torium Helsinki 

and Gerttula, V.G. U.S. Patent 3,045,051 July 17, 1962 assigned to Crown Zellerbach Corp. 

50 grams of crude, tarry curare as received in commerce and containing about 20% of d-tubocurarine are suspended in 400 cc of 0.5 N methanolic potassium hydroxide, and the mixture is boiled for ten minutes. The dark brown insoluble material is filtered off and the filtrate is treated with 50 cc of methyl iodide and refluxed gently for about 8 hours. 

An additional amount of 25 cc of methyl iodide is added to the reaction mixture and the refluxing is continued for 8 hours. 

The reaction mixture is evaporated to a small volume, whereupon the d-tubocurarine dimethyl ether iodide precipitates. The precipitate is filtered off and dissolved in boiling water. The hot solution is treated with a small amount of decolorizing carbon, the carbon filtered off and the filtrate cooled to about 0°C. The dimethyl ether of d-tubocurarine iodide crystallizes in white crystals which melt at about 267°-270°C with decomposition. 

Chemical Abstracts Registry No. 7601 -55-0 Trade Name Manufacturer 

---

Dimethyl tubocurarine Iodide Cyanacetamid Ethionamide Protionamide Cyanamide Albendazole Butalamine HCl Cimetide Cyanoacetamide Allopurinol Cyanoacetic acid Aminometradine Amisometradine Cyclopentamine HCl Sulindac... 

Synonyms. Dimethyl Tubocurarine Iodide Dimethyltubocura-rine Iodide. 

McCullough LS, Stone WA, Delaunois AL, Reier CE, Hamelberg W. The effect of dimethyl tubocurarine iodide on cardiovascular parameters, postganglionic sympathetic activity, and histamine release. Anesth Analg 1972 51(4) 554-9. 

A synthetic route to ( )-0,f>-dimethyltubocurarine iodide (CXXV), via the racemate of 0,0-dimethylbebeerine (CXXIII), was announced in 1959 by Tolkachev and his collaborators (94). It started by the condensation of 3-methoxy-4-hydroxyphenethylamine with 4-benzyloxy-phenylacetic acid to give the amide CXXVI. Reaction of the potassium salt of the latter with the methyl ester of 3-bromo-4-methoxyphenyl-acetic acid in the presence of copper powder gave compound CXXVII. This on condensation with 3-methoxy-4-hydroxy-5-bromophenethyl-amine afforded compound CXXVIII, which was methylated to CXXIX. The latter compound was cyclized with phosphorous oxychloride to the dihydroisoquinoline derivative CXXX. Debenzylation of CXXX followed by intramolecular Ullmann condensation yielded compound CXXXI. The latter was converted to racemic dimethylbebeerine (CXXIII) by reduction with zinc dust in acetic acid followed by methyla-tion. Finally, treatment of ( + )-CXXIII with methyl iodide furnished the dimethyl ether of ( + )-tubocurarine iodide, identified by comparison of its UV-spectrum with that of the dimethyl ether of natural tubo-curarine iodide and by melting-point determination of a mixture of the two specimens. 

Tubocurarine iodide and its isomers have been prepared from the amide-ester... 

Intocostrin is standardized so that one unit is equivalent to 0.15 mg. d-Tubocurarine iodide. 

O -Dimethylchondrocmarine diiodide Tubocmaranimn, 6,6, T, 12-tetramethoxy-2,2,2, 2 -tetramethyl-, diiodide Dimethyl Tubocurarine Iodide U.S.P., Dimethyl Tubocurarine IodideN.F. ... 

Dihydrostreptomycin sulfate Dihydrotachysterol Dihydroxyanthraquinone Dimethisoquin Dimethisoquin hydrochloride Dimethyl tubocurarine iodide Diphenadione Diphenhydramine Diphenhydramine hydrochloride Diprotrizoic acid Doxylamine Doxylamine succinate... 

---