Codeine, Narcotine, Papaverine

Codeine, narcotine, papaverine, papaverrubine D, rhoeadine, thebaine... 

Experiments in the selection of poppies for morphine production have also been made in Germany by Kiissner. The yields from capsules of two selections, over two years, were morphine 0-257 to 0-544 per cent, and codeine 0-011 to 0-029 per cent. From seven commercial varieties grown in plots of 50 square metres, the yields in grammes per square metre were seeds 141 to 200, capsules 65 to 116, morphine 0-123 to 0-471 and non-phenolic bases (codeine, thebaine, papaverine, narcotine, etc.) 0-043 to 0-131. 

The first scheme for the separation of the six chief alkaloids of opium, VIZ., morphine, codeine, thebaine, papaverine, narcotine and narceine, is probably that of Plugge. Much later Kljatschkina investigated for each of these six bases the properties by means of which isolation and estimation could probably be effected and, on the basis of the results, devised a plan for such analyses. More recently Anneler has published a detailed account of a scheme with the same objective. l Attention had already been given to complex, systematic analyses of this kind, in connection with examination of the mixtures of opium alkaloids, which have long been in use in medicine in these at first only morphine and other alkaloids were determined, but in the more recent schemes provision is made for the estimation of each alkaloid. ... 

The processes used in the manufacture of morphine are believed to be still based on that described by the Scottish chemist Gregory,in 1833, with improvements devised by Anderson. A description has been published by Schwyzer, who also deals with the manufactme of codeine, narcotine, cotarnine, and the commercially important morphine derivatives, diamorphine (diacetylmorphine), and ethylmorphine (morphine ethyl ether). More recently Barbier has given an account of processes, based on long experience in the preparation of alkaloids from opium. Kanewskaja has described a process for morphine, narcotine, codeine, thebaine and papaverine, and the same bases are dealt with by Chemnitius, with the addition of narceine, by Busse and Busse, and by Dott. It is of interest to note that a number of processes for the extraction and separation of opium alkaloids have been protected by patent in Soviet Russia. ... 

A characteristic feature of the action of the opium alkaloids is their simultaneous depressing and exciting action on the central nervous system. In this respect there is no clear line of demarcation between the morphine group—morphine, codeine and thebaine—and the papaverine-narcotine group, and as the series is ascended in the order, morphine, papaverine, codeine, narcotine, thebaine, narcotic action diminishes and power of rellex stimulation increases until in thebaine a strychnine-like effect is exhibited. 

Soaking plants parts in alcohol (ethanol) creates a tincture. In this process, pharmacologically active constituents of the plant are extracted by the alcohol. Tinctures do not contain the complete spectrum of substances that exist in the plant or crude drug, only those that are soluble in alcohol. In the case of opium tincture, these ingredients are alkaloids (i.e., basic substances of plant origin) including morphine, codeine, narcotine = noscapine, papaverine, narceine, and others. 

Capillary electrophoresis is suitable for use to separate a wide spectrum of both large and small biological molecules. This method was used for analysis of opium alkaloids such as thebanine, codeine, morphine, papaverine and narcotine. 

Janicot et al. presented the separation of opium alkaloids using sub-critical and supercritical fluid chromatography [20]. Carbon dioxide-meth-anol-triethylamine-water mixtures were used as the mobile phase with packed aminopropyl or bare silica columns. The influence of aminated polar modifiers such as methylamine, ethylamine, and triethylamine was studied. Figure 7.15 shows the separation of six opium alkaloids narcotine, papaverine, thebaine, codeine, cryptopine, and morphine on a Lichrosorb Si-60 column. The method gave comparable results with HPLC. 

Contains more than a score of alkaloids, including morphine, narcotine, papaverine, and codeine, which act to relax smooth muscle, relieve pain, and cause sedation by depressant effect on cerebral cortex, hypothalamus, and medullary centers. It is indicated in the relief of moderate to severe pain associated with ureteral spasm not responsive to nonnarcotic analgesics and to space intervals between injections of opiates. 

Also analyzed acetaminophen, acetylcodeine, acetylmorphine, aminopyrene, aminopyrine, amobarbital, amphetamine, antipyrine, benzocaine, butabarbital, caffeine, cocaine, codeine, diamorphine, diazepam, diethylpropion, DMT, ephedrine, glutethimide, Lampa, lidocaine, LSD, MDA, mecloqualone, mescaline, methamphetamine, methapyrilene, meth-aqualone, methpyrilene, morphine, narcotine, papaverine, PCP, pentobarbital, phencyclidine, phendimetrazine, phenmetrazine, phenobarbital, phentermine, phenylpropeinolam-ine, procaine, quinidine, quinine, secobarbital, strychnine, TCP, tetracaine, thebaine, theophylline... 

The seasonal variations of the alkaloids and the areas of occurrence of F. officinalis and M. microcarpa have been studied (217, 839). A similar paper was devoted to P. somniferum (513, 840) an analysis revealed that a general accumulation of alkaloids, especially the hydrophenanthrene group, occurred one day after the flower had opened. This coincides with the peak of the pollination period. At that period, besides the principal opium poppy latex alkaloids (morphine, codeine, thebaine, papaverine, and narcotine), several other Dragendorff positive compounds were detected. The lysosomal property and accumulation of the alkaloids in vacuoles of Chelidonium majus have been described (841). 

Colchicum cornigerum on the basis of an X-ray analysis of its methiodide. A review on the opium poppy Papaver somniferum describing its diverse uses and effects has appeared.Apparently the positive identification of morphine, codeine, thebaine, papaverine, and narcotine in unknown resins and powders may be taken as evidence that they are derived from P. somniferum. The yield and alkaloid content of P. somniferum capsules upon fertilization has been determined. ... 

When nitration is carried out under the described conditions, the presence of narcotine, papaverine, or codeine does not interfere. Heroin can be determined after acid hydrolysis of the acetyl group. 

A faster gas-chromatographic method was developed by Furmanec Dmytro (1974) for the simultaneous determination of morphine, codeine, thebaine, papaverine, and narcotine alkaloids based on complete separation on a column packed with a 50 50 mixture of OV-17 phenyl-methylsilicone and SE-30 silicone gum on chromosorb W. Standard deviation for the individual alkaloid was between 0.05 to 0.18%. 

HPLC Analysis. One pi of the aliquot, filtered through a Millipore filter (pore size 0.45 pm) is injected into the LC system. Morphine, codeine, thebaine, papaverine, and narcotine are eluted at the retention times of 12.16, 16.20, 21.09, 25.64, and 29.16min, respectively. Alkaloid percentage is then estimated with the help of linear calibration curves of these alkaloids, obtained by plotting peak area against the quantity of alkaloid injected. Recovery of these alkaloids ranges from 95-100%. 

Fig. 2 Densitogram and videoscan from 2D-TLC of isoquinoline alkaloids separated on silica layer by use of aqueous methanol (8%) with 1% ammonia as the first direction eluent and multicomponent non-aqueous eluent with 0.1 M DBA as the second direction eluent. N—noscapine, Na—narcotine, Nc—narceine, G—glaucine, E—emetine, C—codeine, P—papaverine, Pr— protopine, T— tubocurarine. Source From the effect of chromatographic conditions on the separation of selected alkaloids on silica layers, in J. Planar Chromatogr. ...

Among the numerous families of drugs, in this chapter, we have focused our attention on the most widely used methods of analysis found in the literature for the determination of six of the major alkaloids of the poppy plant (Papaver somniferum) named morphine, codeine, thebaine, papaverine, narcotine, and narceine. The choice of method will depend on the resources and equipment available to the analyst in the forensic laboratories, the legislative system in which the analyst is working, and the different forensic samples where... 

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