Papaver

The actions of the naturally occurring materials now known as alkaloids were probably utilized by the early Egyptians and/or Sumarians (1). However, the beginnings of recorded, reproducible isolation from plants of substances with certain composition first took place in the early nineteenth century. Then in close succession, narcotine [128-62-1] (1, now called noscopine, C22H23NOy) (2) and morphine (2, R = H) (3) (both from the opium poppy, Papaver somnijerum E.) were obtained. 

Opium is the dried, powdered sap of the unripe seed pod of Papaver somniferum, a poppy plant indigenous to Asia minor. Theophrastus described its medical properties in the third century BC, but the Sumerians, ca BC 4000, probably perceived its utility. Arab physicians knew of the dmg, and Arab traders carried it to the Orient where it was used as a treatment for dysentery. Paracelsus is credited with repopularizing the dmg in western Europe in the early sixteenth century by formulating opium into "laudanum", which is still in use. More than 20 different alkaloids (qv) of two different classes comprise 25% of the weight of dry opium. The benzylisoquinolines, characterized by papaverine [58-74-2] (1.0%), a smooth muscle relaxant, and noscapine [128-62-1] (6.0%), an antitussive agent, do not have any analgesic effects. The phenanthrenes, the second group, are the more common and include 10% morphine (1, = R = H), 0.5% codeine [76-57-3], C gH2 N03, (1, R = H, R = CH3), and 0.2 thebaine [115-37-7], C 2H2 N03, (2). 

In these equations, [L = specific growth rate coefficient, v = specific rate of substrate uptake, t = time, x = biomass concentration, Sj = intracellular substrate, and Cj = concentration of intracellular substrate. Several examples where these equations can be applied include nitrogen hmitations in M. citrifolia cultures and phosphate hmited growth in C. roseus, N. tahacum, a.nd Papaver. somniferum. 

OF THE ALKALOIDS OF PAPAVER SOMNIFERUM IN THE EXPERT-CRIMINAL OBJECTS... 

The reaction between organic cation (OC) of the alkaloids of Papaver Somnifeiaim and heteropoly anion (HPA) was studied by the... 

The influence of factor series to electrode characteristics has been established. Dependency of the potential of ISE from concentration of defined substance is linear in interval of concentration l lO - l lO mol/1 at the pH 2,0-6,5. Slopping of the graduated graph form 55-56 mV/pC for single-chai ge cation. Potentiometric factors of the selectivity K,, ISE for alkaloids of Papaver Somnifemm has been determined. 

A method is proposed of ionometric determination of the alkaloids of Papaver Somnifemm in the expert-criminal objects. This method is express, selective and characteristic of a high sensitivity (10 mole per liter) and good metrological chai acteristics. 

ALKALOIDS OF OTHER PAPAVER SPP. For the following papaveraceous alkaloids neither constitutional formulas nor group relation-... 

Opium (Papaver somniferum) Benzylfsoquinolines Phthalide isoquinolines Morphine Sub-group, Sinomenium acutum Other Papaver spp. Rhoeadine, etc.. ... 

The Apomorphine-derived alkaloid PO-3 (129) was isolated as violet needles after crystallization from acetone and ether from Papaver orientale (66MI2), but was not found in the green solutions of autoxidized apomorhine hydrochloride (62M941, 68HCA683) (Scheme 51). No anion was detected by elemental analysis. The pA"a of PO-3 is 3.88 0.02 in 50% ethanol. The IR spectrum displays no carbonyl absorption between 1650 and 1700 cm (69MI2). The UV absorption maxima of PO-3 are in agreement with the formulation of a mesomeric betaine [T-max (EtOH) = 310... 

The papaver alkaloid Narcotoline (265) can be converted into the yellow colored Cotarnoline (267) on hydrolysis which adopts a zwitterionic ground state (56MI1, 57MI1) (Scheme 87). The corresponding dihydro derivative was also identified in nature. The UV spectrum of the zwitterionic Tarkonine (268), which forms red crystals from acetone, is shifted bathochromically in comparison to the chloride. Tarkonine is a very weak base (pA b = 9.58), which is well in accord with the formation of an inner salt, and Cotarnoline (267) is a stronger base than Tarkonine (268) (pA b = 9.15). The pK values are larger than 13 (66MI3). The methylated derivative of Narcotoline is Narcotine (266). 

Many alkaloids have pronounced biological properties, and a substantial number of the pharmaceutical agents used today are derived from naturally occurring amines. As a few examples, morphine, an analgesic agent, is obtained from the opium poppy Papaver somnifemm. Cocaine, both an anesthetic and a central nervous system stimulant, is obtained front the coca bush Erythroxylon coca, endemic to upland rain forest areas of Colombia, Ecuador, Peru, Bolivia, and western Brazil. Reserpine, a tranquilizer and antihypertensive, comes from powdered roots of the semitropical plant Rauwolfia serpentina. Ephedrine, a bronchodilator and decongestant, is obtained front the Chinese plant Ephedra sinica. 

Opium is an extract of the juice of the poppy Papaver somnifemm, which contains more than 20 distinct alkaloids, including morphine, codeine and papaverine. 

The term opioid refers to any exogenous substance that acts as an agonist at any of several receptors. Opioid antagonists are drugs that bind to a receptor but produce no actions. The poppy plant, Papaver somniferum, from which opium is obtained, is grown in many areas of the world. Morphine constitutes 10% of opium, and codeine can be obtained direcdy from opium. Semisynthetic opioids such as heroin and oxycodone are obtained directly or indirectly from morphine. There are other distinct chemical classes of drugs with opioid actions, including the methadones. 

Fig. 2.3 Compounds 10-17 fromAloe Compound 18 from Aspalathus linearis. Compound 18.1 from Papaver aculeatum...

The genus Papaver consists of 80 species (Mabberley, 1997, p. 525), nearly all of which are Northern Hemisphere in occnrrence. One species occnrs in the Cape Verde Islands and another, the subject of this entry, is found in South Africa and is naturalized in Australia. Papaver aculeatum Thunb. (P gariepinun Burch, ex DC P. horridum DC) occurs widely in South Africa in areas characterized by summer rainfall and... 

Langlois, A., Mulholland, D. A., Crouch, N. R. and Grace, O. M. 2004. Aporphine alkaloid from Papaver aculeatum (sect. Horrida Papaveraceae) of southern Africa. Biochem. Syst. Ecol. 32 1087-1090... 

The opiate alkaloid, papaverine, from Papaver somniferum is an anti-spasmodic, vasodilator, and smooth muscle relaxant. Its total synthesis has been studied since Pictet and Gams early work in 1909 and has since been followed up by various industrial syntheses up till the early 1950s using important industrial commodities as vanillin, acetovanillone, veratraldehyde (methylvanillin), and homoveratric acid as starting materials (see Figure 4.50). Table 4.23 summarizes the results of the five synthetic plans for this natural product. All are convergent... 

The development of the first effective analgesic drug, opium, was almost certainly adventitious, and occurred in prehistoric times. The use of the dried exudate from slitting the immature capsule of the opium poppy, Papaver somniferum, as an analgesic, sedative and euphoriant, has a long folkloric history. Isolation of the principal active component morphine (1) as a pure crystalline compound represented one of the early landmarks in organic chemistry. 

The starting material for these 14-hydroxy compounds is the opium alkaloid thebaine (9). Although present in only small amounts in the alkaloid fraction from Papaver somniferum, it constitutes the major component (as much as 26% of the dried latex) from a... 

G. Sariyar and M. Shamma [Phytochemistry 25, 2403 (1986)] recently reported the isolation of the corresponding aldehyde macrantaldehyde and macrantoline (6) and macrantoridine (7) from capsules of Papaver... 

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