Opium poppy Papaver somniferum

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. 

UNTERLINNER, B LENZ, R KUTCHAN, T.M., Molecular cloning and functional heterologous expression of codeinone reductase The penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum, Plant J., 1999,18,465-475. 

Francis PS, Adcock JL, Costin JW et al (2008) Chemiluminescence detection of opium poppy (Papaver somniferum) alkaloids. J Pharm Biomed Anal 48 508-518... 

Before delving into ways the living world uses its special chemicals, we should note that these compounds touch our own lives in important ways. For millennia, humans have been borrowing natural chemicals for their own purposes, most often as drugs. Our oldest medicine is opium, which we prepare from the opium poppy (Papaver somniferum) today much as Mediterranean peoples did four thousand years ago. Just as we do, these early communities valued opium for its ability to kill pain and impart a sense of well-being. The principal constituent responsible for these effects is a chemical compound called morphine, which remains unsurpassed in its ability to control severe pain. In poppies, morphine s toxicity and bitterness presumably repel herbivores looking for a tasty meal. 

The opium poppy (Papaver somniferum) is a blue-grey annual plant growing 30 to 150 cm in height (Robbers et al. 1996 Gruenwald et al. 

The opium poppy (Papaver somniferum). Reprinted from Culbreth DMR. (1927). Materia Medica and Pharmacognosy, 7th ed. Philadelphia Lea 8i Febiger. 

Morphine is the major alkaloid in opium, the dried latex obtained from the opium poppy, Papaver somniferum. About 25% of the mass of opium is composed of alkaloids, with morphine constituting about 12-15%. Morphine is a powerful analgesic, and remains one of the most valuable for relief of severe pain. However, most of the morphine extracted from opium is processed further to give a range of semi-synthetic drugs, with enhanced or improved properties. A means of extracting morphine from the other alkaloids in opium is thus desirable. 

Opium is a cmde exudate obtained from the opium poppy Papaver somniferum, and it provides several medicinally useful alkaloids. One of these is codeine, which is widely used as a moderate analgesic. Opium contains only relatively small amounts of codeine (1-2%), however, and most of the codeine for dmg use is obtained by semi-synthesis from morphine, which is the major component (12-20%) in opium. Conversion of morphine into... 

Grothe, T., Lenz, R. and Kutchan, T. M. 2001. Molecular characterization of the salu-taridinol 7-0-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. Journal of Biological Chemistry, 276(33) 30717-30 723. 

Morphine and cocaine Morphine is medically the most important alkaloid present in opium. Opium itself consists of the dried milky exudate extracted from unripe capsules of the opium poppy (Papaver somniferum), which is grown mainly in Asia, but also in some parts of India and China. Morphine is a powerful analgesic and has been used to treat severe pain. However, its addictive properties complicate its long-term medical use and it is also a drug of abuse. In addition to morphine, opium also contains codeine, which has similar, but weaker, actions. 

The word opium comes from the Greek opos (juice) or opion (poppy juice). According to the Oxford English Dictionary, opium is a reddish-brown, strongiy scented addictive drug prepared from the thickened dried iatex of the unripe cap-suies of the opium poppy, Papaver somniferum, used illicitly as a narcotic, and occasionally medicinally as a sedative and analgesic. ... 

The opium is obtained from the opium poppy Papaver somniferum. It contains two type of alkaloids e.g. phenanthrene derivatives (morphine, codeine thebaine) and benzyl isoquinoline derivatives (papaverine and noscapine). 

Unfortunately, to feel pain is an essential condition for survival. Pain-initiated avoidance behavior protects the individual. Morphine, obtained from opium, from the juice of the opium poppy (Papaver somniferum), has been known for millennia to alleviate pain. As mentioned in Chapter 5, endogenous opioids have also been identified. The word opioid is now used to refer to all drugs with morphine-like actions. The structure of morphine is shown in Figure 11.11. Diacetylmorphine (heroin) is made by acetylation at the 3 and 6 positions. 

Isolation of the alkaloids from the latex of the opium poppy, Papaver somniferum, led to the identification of over 20 compounds (Fig. 11.1). The most abundant alkaloids were morphine (1), codeine (2), thebaine (3), noscapine (4), and papaverine (5). 

We switch to a completely different kind of alkaloid made from a different kind of amino acid. The benzyl isoquinoline alkaloids have a benzyl group attached to position 2 of an isoquinoline ring. Usually the alkaloids are oxygenated on the benzene ring and many are found in opium poppies (Papaver somniferum). For all these reasons papaverine is an ideal example. 

The opium poppy Papaver somniferum contains two useful analgesic alkaloids, morphine and codeine, as well as thebaine, which not only may be... 

The medical uses of morphine alkaloids have been known at least since the seventeenth century, when mide extracts of the opium poppy. Papaver somniferum, were used for the relief of pain. Morphine was the first pure alkaloid to be isolated from the poppy, but its clgsc relative, codeine, atso occurs naturally. Codeine, which is simply the rtethyl ether of morphine and is convert to morphine in the body, is ufed in preacription cough medicines and as an analgesic. Heroin, another close relative of morphine, does not occur naturally but is synlhesiiced by dlacotylalioii nf morphine. 

The benzylisoquinolines are formed from two molecules of fhe aromafic amino acid, tyrosine. In the past ten years, this pathway has been probed at the enzyme and gene level. The recent linking of the phloem-specific expression of tyrosine/Dopa decarboxylase (TYDC) genes with the bios)mthesis of the isoquinoline alkaloids in the opium poppy, Papaver somniferum (Facchini and De Luca, 1994, 1995, 2008 Liscombe and Facchini, 2008), and the association with alkaloid accumulation as part of the plant defence mechanism (Wink, 1993 Facchini et al, 1996) are of particular interest in furthering our knowledge of the location of alkaloid biosynthesis. 

Weid, M., Ziegler, J. and Kutchan, T.M. (2004) The role of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum. Proc. Natl. Acad. Sci. USA, 101,13957-4962. 

Use of the opium poppy (Papaver somniferum) to ameliorate pain dates back thousands of years, and the active metabolite morphine (2) was isolated first from its extracts in 1806 followed by codeine (53) in 1832 (27, 28). Morphine and its derivatives are agonists of opiate receptors in the central nervous system and are some of the most effective pain relievers known and prescribed for postoperative pain. Morphine and codeine differ by substitution by methyl ether. Unfortunately, addictive properties of these compounds limit their use. Efforts have been made to reduce the addictive properties of morphine, which resulted in a semisynthetic derivative buprenorphine (54) (29). This compound is 25 to 50 times more potent than morphine with lower addictive potential and has been indicated for use by morphine addicts. 

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