Deadly nightshade plant

Atropine is a racemic compound but the (S)-enantiomer occurs in henbane (tfyoscyamus niget ) and was given a different name, hyoscyamine, before the structures were known. In fact, hyoscyamine racemizes very easilyjust on heating in water or on treatment with weak base. This is probably what happens in the deadly nightshade plant. 

Atropine is an alkaloid isolated from Atropa bellactonna, the deadly nightshade plant. In the Renaissance, women used the juice of the berries of the nightshade to enlarge the pupils of their eyes for cosmetic reasons. Atropine causes an increase in heart rate, relaxes smooth muscles, and interferes with nerve impulses transmitted by acetylcholine In higher doses atropine is poisonous, leading to convulsions, coma, and death. 

One of several similar substances, collectively known as the belladonna alkaloids, which are extracted from the deadly nightshade plant (Atropa belladonna). Atropine is used mainly to treat disorders of the digestive tract such as excessively rapid movements of the stomach and bowel, overacidity, and ulcers, because it (1) reduces the amounts of digestive secretions, and (2) slows the motions of the digestive organs. Some common side effects are dryness of the mouth and constipation. 

FIGU RE 5.4. Four active chiral compounds isolated from the "deadly nightshade" plant. 

Atropiae (41), isolated from the deadly nightshade Airopa belladonna L.) is the racemic form, as isolated, of (—)-hyoscyamine [which is not isolated, of course, from the same plant but is typically found ia solanaceous plants such as henbane (HyosQiamus mgerl. )]. Atropiae is used to dilate the pupil of the eye ia ocular inflammations and is available both as a parasympatholytic agent for relaxation of the intestinal tract and to suppress secretions of the saUvary, gastric, and respiratory tracts. In conjunction with other agents it is used as part of an antidote mixture for organophosphorus poisons (see Chemicals in war). 

Atropine and its ether analog scopolamine (hyoscine) are potent alkaloids that are found as active compounds in a large number of plants around the world (belladonna alkaloids). The deadly nightshades ( European bittersweet, Solanum dulcamara or belladonna, belladonna) were used in the Mid-... 

Other plants of the nightshade family, including Atropa belladonna (deadly nightshade), Hyoscyamus niger (black henbane), and Datura stramonium (Jimson weed), contain atropine-like toxins that are anticholinergic, blocking the muscarinic receptors. An incidence in southern Utah of cattle poisoned on black henbane, with many death losses, was recently reported (Pfister, 2003). Atropine and atropine-like alkaloids are discussed Section 2.2.1.7. 

This family is characterized by producing substances that have dramatic effects on humans and animals the toxins in deadly nightshade, mandrake, and datura the nicotine in tobacco plants and the burning capsaicin in chili peppers. But it also contains cool, juicy sweet tomatoes and bell peppers eggplants, with their rich, creamy flesh and the ultimate in comfort food—the potato. 

The tropane alkaloids (—)-hyoscyamine and (—)-hyoscine are found in the toxic plants deadly nightshade (Atropa belladonna) and thornapple (Datura stramonium) and are widely used in medicine. Hyoscyamine, usually in the form of its racemate atropine, is used to dilate the pupil of the eye, and hyoscine is employed to control motion sickness. Both alkaloids are esters of (—)-tropic acid. 

Atropine-like effects - dry mouth, dilated pupils, confusion, hallucinations, memory lose Solanaceae family -jimsonweed, henbane, deadly nightshade (Atropa belladonna), angles trumpet (atropine and scopolamine) Clinical effects of many of the plants recognized since ancient times. Deaths are rare but children vulnerable. Hallucinations from muscarine and psilocybin... 

Belladonna alkaloid-containing plants Deadly nightshade Angel s trumpet Jimsonweed... 

Atropine and its naturally occurring congeners are tertiary amine alkaloid esters of tropic acid (Figure 8-1). Atropine (hyoscyamine) is found in the plant Atropa belladonna, or deadly nightshade, and in Datura stramonium, also known as jimsonweed (Jamestown weed), sacred Datura, or thorn apple. Scopolamine (hyoscine) occurs in Hyoscyamus niger, or henbane, as the /(-) stereoisomer. Naturally occurring atropine is /(-)-hyoscyamine, but the compound readily racemizes, so the commercial material is racemic d,/-hyoscyamine. The /(-) isomers of both alkaloids are at least 100 times more potent than the d(+) isomers. 

The solanaceae alkaloids and other other sources of antimuscarinics affect the CNS. They can produce hallucinations in addition to their effects on the peripheral nervous system. Witchcraft of the Middle Ages produced mixtures of plants - deadly nightshade, monkshood, and hemlock among them - as "flying ointments". The combined toxins disturbed the rhythm of the heart and led to delirium which could create a sensation of rising and falling, that is, flying. 

The tropane alkaloids (—)-hyoscyamine and (—)-hyoscine are among the most important of the natural alkaloids used in medicine. They are found in a variety of solanaceous plants, including Atropa belladonna (deadly nightshade), Datura stramonium (thornapple) and other Datura species, Hyoscyamus niger (henbane), and Duboisia species. These alkaloids... 

Note The best-known antimuscarinic or anticholinergic drugs are the belladonna alkaloids. The major drugs in this class are atropine, hyoscyamine, and scopolamine. A number of plants belonging to the potato family (Solanaceae) contain similar alkaloids. Atropa belladonna (deadly nightshade), Hyoscyamus niger (henbane), Datura stramonium (jimsonweed or thorn apple), and several species of Scopolia also contain belladonna alkaloids. 

Itself a deadly poison derived from belladonna or other nightshade plants (see Chapter 19), atropine must be administered with great care. The organophosphate residues can be bound with oximes to release acetylcholinesterase. This is shown below for the reaction of organophosphate-bound acetylcholinesterase enzyme with pralidoxime ... 

Alkaloids were known in ancient times because they are easy to extract from plants and some of them have powerful and deadly effects. Any plant contains millions of chemical compounds, but some plants, like the deadly nightshade, can be mashed up and extracted with aqueous acid to give a few compounds soluble in that medium, which precipitate on neutralization. These compounds were seen to be like alkali and Meissner, the apothecary from Halle, in 1819 named them alkaloids . Lucrezia Borgia already knew all about this and put the deadly nightshade extract atropine in her eyes (to make her look beautiful atropine dilates the pupils) and in the drinks of her... 

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