Opium Alkaloids

Other Names Opiate, opiates, opium compounds The study of opium and the isolation of its constituents ranks among the most important achievements in the history of pharmacology (cf. Papaver somniferum). In ancient times, opium was already known as the best of all analgesics (cf. soporific sponge). The isolation of morphine from opium revolutionized pain therapy in Europe. No other component of opium has a comparably powerful effect. The potency of morphine would not be exceeded until heroin (diacetylmorphine) was synthesized (Snyder 1989). Subsequent pharmacological research has led to the creation of numerous morphine analogs (fentanyls), some of which are as much as 7,500 times more potent than morphine (Sahihi 1995,31 ff.*). The opium alkaloids codeine and morphine have become culturally significant as psychoactive substances. Papaverine is used in medicine as a treatment for impotence. Some opium alkaloids are also found in other Papaver species (Papaver spp.), although these species usually contain only traces of these substances (Khanna and Sharma 1977; Ktippers et al. 1976; Phillipson et al. 1973; Phillipson et al. 1976). Aporphines, whose structures are analogous to those of the opium alkaloids, occur in Papaver fugax Poir. [syn. Papaver caucasicum M.-B., Papaver floribundum Desf.] and Nymphaea ampla. Other substances related to the opium alkaloids are present in Argemone mexicana, Eschscholzia californica, Nuphar lutea, and Papaver spp.

Literature See also the entries for Argemone mexicana, Papaver somniferum, Papaver spp., codeine, morphine, and papaverine. Khanna, P., and G. 1. Sharma. 1977. Production of opium alkaloids from in vitro tissue culture of Papaver rhoeas 1. Indian Journal ofExperimental Biology 15:951-52. Krikorian, A. D., and M. C. Ledbetter. 1975. Some observations on the cultivation of opium poppy (Papaver somniferum 1.) for its latex. Botanical Review 41:30-103. Ktippers, F. J. E. M., C. A. Salmink, M. Bastart, and M. Paris. 1976. Alkaloids of Papaver bracteatum: Presence of codeine, neopine and alpinine. Phytochemistry 15:444-45. Phillipson, J. D., S. S. Handa, and S. W. EI-Dabbas. 1976. N-oxides of morphine, codeine and thebaine and their occurrence in Papaver species. Phytochemistry 15:1297-1301. Phillipson, J. D., G. Sariyar, and T. Baytop. 1973. Alkaloids from Papaver fugax of Turkish origin. Phytochemistry 12:2431-34. Scully, Rock, with David Dalton. 1996. An American odyssey: Die legendare Reise von Jerry Garcia und den Grateful Dead. St.Andra-Wordern: Hannibal Verlag. Snyder, Solomon H. 1989. Brainstorming: The science and politics ofopiate research. Cambridge and London: Harvard University Press. The Constituents of Opium The composition of the alkaloid mixture can vary greatly, depending upon the strain of poppy, the location of cultivation, and the processing technique (Krikorian and Ledbetter 1975). 1. Isocholine derivates codamine* cryptopine*   gnoscopine*   hydrocotarnine*   laudanindine (= tritopine)*   dl-Iaudanine*   laudanosine*   norlaudanosine*   narceine (= narceinum) 0.1-0.2% 1-narcotine (= narcotine = noscapine) 1-11% oxynarcotine*   papaverine 0.5-10% protopine* (also in Papaver rhoeas,   Argemone mexicana, and   Eschscholzia californica)   reticuline*   xanthaline (= papaveraldine)*       II. Bases that yield phenanthrene derivatives when broken down   codeine 0.2-4% morphine 2.8-23% neopine*   porphyroxine*   pseudomorphine*   thebaine (also in Papaver bracteatum) 0.1-4% III. Other bases   lanthopine*   meconine*   oripavine* (also in Papaver orientale)   papaveramine*   rhoeadine*   Alkaloids marked with * are present in only trace amounts.