Papaver somniferum, morphine from

Opium, the sun-dried latex of the unripe fruit of Papaver somniferum, cultivated from early times for this drug, contains at least 23 alkaloids. Of the major alkaloids three—morphine, codeine, and thebaine—contain the morphinan ring system. 

Opiates are a group of naturally occurring compounds derived from the juice of the poppy Papaver somniferum. Morphine is the classic opiate derivative used widely in medicine heroin (diacetylmorphine) is a well-known, highly addictive street narcotic. 

An example of this are the concentrations of the isoquinoline alkaloids morphine, codeine, and thebaine (D 22.1.2) in the latex of Papaver somniferum. Morphine concentrations peak in the morning codeine, at noon and thebaine gradually increases from 6 am until the late evening... 

Morphine (5) and codeine (methylmorphine) (6), two major morphinan-type alkaloids with an isoqninoline skeleton, are extracted from opium, the dried milky sap released from the immature finits of poppies (Papaver somniferum). Morphine and codeine can interact with opioid receptors distribnted in brain tissnes and the periphery, and are most widely nsed as narcotic analgesics, with codeine also having an antitussive effect [4, 25, 32]. 

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. 

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. 

Opium The extract from Papaver somniferum containing morphine and codeine. 

Morphine (10) and codeine (11), constituents of opium, are the most interesting alkaloids found in nature. Morphine is also the oldest alkaloid isolated, in 1805, by the German pharmacist Sertiimer from opium, the sun dried latex of Papaver somniferum. The structure of morphine with its so-called morphinan skeleton, once called the acrobat under the alkaloids, was finally elucidated in 1952 by the first total synthesis performed by Gates and Tschudi. Many syntheses would follow [26], but all morphine used today, whether legal or illicit, originates in the natural source P. somniferum or its extract, opium. The latex may contain up to 20% morphine. Most legal morphine is converted into the anticough medicine codeine (Table 5.1) by treatment with trimethylanilinium methoxide, whereas almost all illicit morphine is acetylated to the diacetate heroin. 

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. 

Apomorphine hydrochloride (44 Apokyn Bertek, 2004), is a semisynthetic derivative of opium alkaloid morphine (43) isolated from poppy (Papaver somniferum), and it has long been known for its erectile activity at the effective dose of 2-6 mg physicians discovered the effect over 100 years ago, but found the drug, at a much higher dose (ca. 200 mg), to be more suitable for poison victims as an emetic because it also causes serious nausea and vomiting. Apomorphine exerts its erectile effect at the central nervous system the drug has been found to be a non-selective dopamine agonist which activates both Di-like and D2-like... 

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... 

In the past, a number of discoveries have been made in the absence of any knowledge about the receptors or ligands. One of the earliest examples of this kind is morphine (65) which was used for many years as an analgesic agent (as a constituent of opium, extracted from the poppy plant, Papaver somniferum) without... 

Morphine (13), from Papaver somniferum L., is an excellent example of a lead compound from which numerous synthetic derivatives have been... 

The above mentioned reactions are widely used in alkaloid modification. A good example of alkaloid modifications for clinical curation purposes are opioides. Morphine and codeine are natural products of Papaver somniferum. However, the codeine is naturally produced in small amounts. This is one reason why it is produced synthetically from morphine by modification. As codeine is the 3-0-methyl ether of morphine, the mono-O-methylation occurs in the acidic phenolic hydroxyl. Pholcodine is obtained by modification of morphine through alkylation with A-(chloroethyl)morpholine. Moreover, dihydrocodeine, hydro-morphone and heroine are also obtained from morphine through modifications. 

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. 

For centuries opium was used for both medicinal and recreational purposes. Derived from the poppy Papaver somniferum, it contains numerous opiates, the primary one of which is morphine. The term opiate has largely been replaced by opioid, which represents all compounds with morphinelike activity and includes morphine, morphine derivatives, and peptides. Opiate is used to refer to morphinelike drugs derived from the plant and structurally similar analogues. These drugs are frequently referred to as narcotics, a Greek term for stupor, which is scientifically obsolete. Even in its early history, opium presented a problem when it was smoked or taken orally. The introduction of the hypodermic needle and syringe, however, drastically enhanced the euphoric properties of opioids and thereby altered their abuse liability. In addition, the synthesis of heroin resulted in an opioid that was more potent than morphine and ideally suited for intravenous administration. 

Like morphine, codeine is extracted from natural opium, obtained from the poppy plant (Papaver somniferum). Only when it was first discovered and tested was codeine purified directly from opium (see Chapter 1). Today pharmaceutical-grade codeine is synthesized from morphine through the relatively simple chemical modification process of methylation, whereby CHj replaces a hydrogen atom on the morphine molecule. The chemical substitution reaction that takes place (H for CHj) does so at a specific location on the morphine molecule (Figure 3.1) if the substitution were to occur elsewhere on... 

Opium alkaloids are nonpeptide agonists for the opioid peptide hormone receptors. The dried latex of Papaver somniferum (opium), or the seed capsule of the plant itself, are the sources of almost 25 alkaloids. Some simple isoquinolines from opium, like papaverine (5.86), are antispasmodics. The principal alkaloid ( 10% of the total) is morphine (3.11), which is also an isoquinoline (rings C and E) but can addihonally be considered a phenanthrene derivahve (rings A, B, and C). 

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). 

Nature has been a potential source of therapeutic agents for thousands of years. An impressive number of modem dmgs have been derived from natural sources. Over the last century, a number of top selling dmgs have been developed from natural products. Anticancer dmg vincristine from Vinca rosea, narcotic analgesic morphine from Papaver somniferum, antimalarial dmg artemisinin from Artemisia annua, anticancer dmg Taxol from Taxus brevifolia and antibiotic peniciUins from Penicillium ssp. are just a few examples. 

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