Laudanine Laudanosine

Codeine, coptisine, cryptopine, laudanine, laudanosine, morphine, narceine, narcotine, narcotoline, papaverine, papaverrubine A, B, D, E, protopine, sanguinarine, thebaine... 

Benzylisoquinoline Derivatives. Papaverine, C20H21O4N Xanthaline, C20H19O5N dZ-Laudanine, C20H25O4N Laudanidine, C20H25O4N Codamine, C20H25O4N Laudanosine, C21H27O4N... 

Special Reactions of Papaverine. Papaverine undergoes a number of reactions, which are of interest as providing methods of synthesis for other alkaloids, of which examples will be found under laudanosine, laudanine, laudanidine, codamine (pp. 187-195), berberine (p. 331), corydaline (p. 284), and glaucine (p. 311). 

Reviews of recent work on spasmolytic drugs have been published by Raymond and by Blicke, and a detailed account of the action of papaverine and its derivatives, including laudanosine and laudanine with numerous references to literature is given by Krueger, Eddy and bumwalt. ... 

Laudanosine (= Laudanine Papaver somniferum (opium poppy) GABA-R antagonist (100)... 

Isothebaine (= 1-Hydroxy-2,1 1-dimethoxyaporphine) (aporphine isoquinoline) Laudanosine (= Laudanine methyl ether) (benzylisoquinoline)... 

The same treatment with hydrochloric acid when applied to (—)-laudan-osine gave again mixtures of phenolic bases from which a product identical with the opium alkaloid laudanidine [(—)-laudanine, LII] could be isolated. (- -)-Laudanosine furnished the optical isomer of the natural alkaloid under analogous conditions (29). 

Laudanine is also formed in low yields by heating DL-laudanosine with... 

Laudanine was also obtained by Spath and Burger (29) by heating dl-laudanosine with concentrated hydrochloric acid at 100° for twenty minutes. It was the first substance to separate from the mixture of phenolic bases thus obtained. Heating of DL-laudanosine with a nitrobenzene solution of 4.5 moles of anhydrous aluminum chloride (84) gave an 8 % yield of laudanine. 

The synthesis of laudanidine by Spath and Burger (29) followed the pattern used by them in their synthesis of laudanine. Zero-Laudanosine, pre-... 

Under analogous conditions, (+)-laudanosine was cleaved to the enantiomer of natural laudanidine. When the two optical isomers were mixed in solution, laudanine crystallized out, thus confirming the relationship of these three forms. 

The base LIII was also found by Burger (83) in the mother liquors of laudanine obtained by partial demethylation of DL-laudanosine (29). Vice versa, pseudolaudanine can be methylated to laudanosine (33, 42). 

The second proposed pafhway, involving several A-methylated intermediates, begins with the N-methylation of (5)-coclaurine and continues with a hydroxi-lation and an 0-methylation steps to afford (5)-reticuline, which is converted to (5)-laudanine catalyzed by reticuline 7-OMT. 3 -OMT, laudanosine A-demethylase (LNdeMT), and dehydrogenase (deHase) enzymes catalyze the three latest steps, leading to the formation of papaverine [113]. 

Isoquinolines Cotamine, eupaverine, hydrocotamine, laudanosine, laudanine, noscapine (narcotine), papaverine, papaveraldine, xanthaline... 

The 0-demethylation of laudanosine has been employed to obtain phenolic bases of the benzylisoquinoline group. Racemic laudanosine, treated with lithium in liquid ammonia with dioxane as a solvent, gave laudanine (LXXIII) when tetrahydrofuran was employed, it afforded 4, 7-di-O-methyllaudanosoline (protosinomenine) 140) (Section IV, B, 2). When the first method was applied to d-( —)- and L-( + )-laudanosine, D-( —)- and L-( + )-laudanidine were obtained 10). 

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