Poppies

Review Problem 4 This compound (TM 78) is an important intermediate in the synthesis of alkaloids Treatment with POCI3 gives the poppy alkaloid papaverine. How would you make TM 78 from simple starting materials ... 

Barnett and colleagues developed a new method for determining the concentration of codeine during its extraction from poppy plants. As part of their study they determined the method s response to codeine relative to that for several potential interferents. For example, the authors found that the method s signal for 6-methoxycodeine was 6 (arbitrary units) when that for an equimolar solution of codeine was 40. 

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. 

Codeiae (2, R = CH3) occurs ia the opium poppy along with morphine (2, R = H) but usually ia much lower concentration. Because it is less toxic than morphine and because its side effects (including depression, etc) are less marked, it has found widespread use ia the treatment of minor pain and much of the morphine found ia cmde opium is converted to codeiae. The commercial coaversioa of morphine to codeiae makes use of a variety of methylating ageats, amoag which the most common are trimethylphenylammonium salts. Ia excess of two huadred toas of codeiae are coasumed anauaHy from productioa faciUties scattered arouad the world. 

Spices and herbs can play an important indirect role in good nutrition. They are not high in nutrient values, but they help to increase the appeal and satisfaction of foods that are highly nutritious. Spices do contain fat, protein and carbohydrates, electrolytic minerals, iron and B vitamins, and others, but even the highest calorie spice, poppy seeds, contains only two to three calories per serving in normal use (12). 

The iaterpretation of forensic toxicology (18) results is often challenging. Courts frequently ask if an amount of dmg detected ia a specimen could cause a specific type of behavior, ie, would someone be under the influence of a dmg at a specific concentration, would a particular dmg concentration cause diminished capacity, or was the dmg the cause of death In a random employee dmg testing case, a worker screened positive for opiates by EMIT and gc/ms analysis of the urine specimen showed low levels of morphine. Although one possibiUty was that the iadividual was a heroia user, a review of foods eaten ia the prior 24 hours suggested a more innocent cause a poppy-seed bagel. 

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). 

Codeine, like morphine, is isolated from the opium poppy. However, the low yield of 0.7—2.5% does not provide sufficient material to meet commercial demands. The majority of marketed codeine is prepared by methylating the phenolic hydroxyl group of morphine. Morphine yields from opium poppy are 4—21%. When prescribed for cough, the usual oral dose is 10—20 mg, three to four times daily. At these doses, adverse side effects are very few. Although the abuse potential for codeine is relatively low, the compound can substitute for morphine in addicts (47). 

More interesting, as regards future developments, are the eiforts now being made to dispense with opium as an intermediate in the production of morphine. The early history of experiments in the direct extraction of the alkaloid from poppy capsules and poppy straw has been recounted by Goris and by Wiiest and Frey. ... 

Wiiest and Frey have pointed out that poppy straw has disadvantages in low yield of morphine and in bulkiness, and prefer poppy heads as a primary material. Many samples of capsules from seven countries were examined by them and found to yield from 0-18 to 0-9 per cent, of morphine, and they conclude that it should be possible to get ripe, dry capsules containing on the average 0-3 to 0-5 per cent, of morphine. Their paper includes a description of a process of analysis, which was found speedy and accurate. 

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. 

In the experiments in Australia, described by Barnard and Finnemore, the average yield of morphine from capsules of two varieties of poppy, ranged from 0- 29 to 0- 39 and from 0- 26 to 0- 30 and from the whole plant from 0-09 to 0-16 and from 0-12 to 0-18 per cent. 

Karrer and Schmid have examined the water-soluble constituents in poppy straw after extraction of the alkaloids, and have recorded the presence of -hydroxybenzaldehyde, vanillin, -hydroxystyrene, meconin and the following acids fumaric, dZ-lactic, benzoic, -hydroxycinnamic, p-hydroxybenzoic, 2-hydroxycinchoninic, vanillic, phthalic, hemipinic and m-hemipinic, with a more highly unsaturated, carboxylic acid J, b.p. 170-570-02 mm., and three unidentified substances Fa , m.p. 271-2° Wx, m.p. 310° (dec.) and Q, m.p. 260° the two latter are free from nitrogen and contain no methoxyl. 

Narcotoline, This alkaloid, isolated from opium-poppy... 

Although morphine has been prepared by total synthesis, the complexity of the molecule makes such an approach unattractive on a commercial scale. The drug in fact is obtained by fractionation of opium obtained from the poppy morphine in turn is used as starting material for various derivatives. If it were not for the importance of these drugs in the clinic, some progress might have been made in eradication of the plant. 

Hom-klee, m. bird s-foot trefoil (Lotus corni-culatus). -kobalt, n. asbolite. -Ibffel, m. horn spoon, -mohn, m. horn poppy (Glau-cium). -quecksilber, n. horn quicksilver (native mercurous chloride), -schicht, /. horny layer, specif, epidermis, -silber, n. horn silver (cerargyrite). -spatel, m. horn spatula, -stein, m. homstone (variety of quartz). 

Klatsch-praparat, n. (Micros.) a smear preparation made by pressing the material between two cover glasses and sliding them apart, -rose, /. corn poppy, klauben, v.t. pick, sort (cap., by hand). 

Mohn, m. poppy, -gewachse, n.pl. (Bot.) Pa-paveraceae. -kapsel, /., -kopf, m. poppy capsule, poppy head. -81, n. poppy-seed oil. molmrot, a. poppy-red. 

Mohn-saft, OT. poppy juice, opium, -samen, ot. poppyseed, -saure,/. meconic acid, -stoff, m. narcotine, -stroh, n. lit., poppy straw (residue from extraction of poppy heads and stems). 

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. 

The intensity and color of the poppies in Monet s painting The Poppyfield, near Giverny are influenced by the acidity or basicity of the soil. Of course artistic license could also have something to do with the intensity and color of the poppies in this painting. 

Rowers and unripe seed capsules of the opium poppy. Within the capsule is a milky, gummy substance that contains the alkaloid moiphine. 

Caffeine occurs in tea leaves, coffee beans, and cola nuts. Morphine is obtained from unripe opium poppy seed pods. Coniine, extracted from hemlock, is the alkaloid that killed Socrates. Fie was sentenced to death because of unconventional teaching methods teacher evaluations had teeth in them in ancient Greece. 

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

Opioid analgesics are the narcotic analgesics obtained from the opium plant. More than 20 different alkaloids are obtained from the unripe seed of the opium poppy... 

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