Poisons coniine

The poison hemlock contains two alkaloids that are poisonous, coniine and coniceine. They act to block the transmission of nerve impulses, which results in death by failure of respiration. The plant is famous for its part in the execution of Socrates in ancient Greece, who was found guilty of corrupting the young and neglecting the gods. The execution was described by Plato in Phaedo, written in 360 bc ... 

Coniine (12), impHcated by Plato in the death of Socrates, is the major toxic constituent of Conium maculatum L. (poison hemlock) and, as pointed out eadier, was apparendy the first alkaloid to be synthesized. For years it was thought that coniine was derived from lysine (24), as were many of its obvious relatives containing reduced piperidine nuclei and a side chain, eg, peUetierine (46). However, it is now known (99) that coniine is derived from a polyketooctanoic acid [7028-40-2] (138), CgH QO, or some other similar straight chain analogue. 

The common hemlock, Conium maculatum, contain five alkaloids. Power and Tutin found a similar mixture in fool s parsley, and a volatile alkaloid resembling coniine i.s stated to occur in certain aroids. According to Svagr, water hemlock Cicuta virosa) owes its poisonous properties to toxin and not to cicutine, a name sometimes used as a synonym for coniine. The toxic properties of hemlock juice have been known ftom very early times thus it was the chief ingredient in the poison administered to criminals by the Greeks. The leaves and the unripe fruits are the parts used in medicine. The following are the names and formulae of the alkaloids —... 

Coniine, C H N. is the toxic principle of the poison hemlock drunk by Socrates. When subjected to Hofmann elimination, coniine yields 5-(iV,N-dimethylamino)-l-octene. If coniine is a secondary amine, what is its structure ... 

The profound physiological effects of alkaloids have been known for centuries. For example, Socrates was put to death with an extract of hemlock, which contains a poisonous alkaloid, coniine. Other alkaloids have long been valued for their beneficial medical effects. Examples include morphine (a painkiller), quinine (used to treat malaria), and atropine (used to treat Parkinson s disease and in eye drops that dilate the pupils). 

Poison-hemlock also has historical significance to researchers because coniine was the first alkaloid discovered, in 1827, and was first synthesized in 1886 (Landenburg, 1886, reviewed in Panter and Keeler, 1989). 

Figure 2.2 Three piperidine alkaloid teratogens from Conium maculatum (poison-hemlock) (a) coniine, (b) y-coniceine, and (c) A-methyl coniine, with accompanying LD50 as determined in a mouse bioassay.

DETAILS - A crude extract of hemlock was used by the ancient Greeks to execute enemies of the state. Plato s description of the death of Socrates is a very detailed account of the symptoms and their progression. Pure coniine has a burning taste similar to low-grade hot sauce and a characteristic odor which should be masked. Hard liquor or pungent spicy foods are best for this. Coniine poisoning is a relatively painless process, but takes several hours and the victim is conscious and aware to the very end. 

Neurotoxic - death Poison hemlock (Conium maculatum) Coniine - neurotoxic alkaloid -poison used by Socrates... 

Piperidine alkaloids such as coniine and (—)-coniceine are very poisonous. They occur in hemlock (Conium maculatum L.), known as a very toxic plant. One of the characteristics of these piperidine alkaloids is smell. Moreover, they are neurotoxins which have acute effects such as chronic toxicity. 

Heterocycles which are not biosynthesized in humans, but which are natural products produced by other life forms, are very important in the history of drug design. This is particularly true of alkaloids containing a piperidine ring. These include coniine (8.87, extracted from poison hemlock, Conium maculatum, a member of the Umbelliferae carrot family), atropine (from Atropa belladonna and other genera of the Solanaceae plant family the plant was called belladonna [ beautiful woman ] since it was used by... 

Coniine Coniine or (5 )-2-propylpiperidine, molecular formula CgHnN, is a poisonous alkaloid found in the hemlock poison and the yellow pitcher plant (Sarracenia flava). Coniine contributes to the foul smell of hemlock. It is a neurotoxin, causes respiratory paralysis and is toxic to all classes of livestock and humans. In 399 BC, Socrates was put to death hy this poison. 

Coniine is a poison found in the spotted hemlock, Conium maculatum. This type of hemlock is found commonly throughout the United States and the world, including SLO County. White disperse flowers on a long purple stalk are routinely mistaken for its nontoxic look-alike - the edible wild parsnip. It was a hemlock brew which Socrates... 

The data shown in Table 2 illustrate the general paucity of comparative toxicity data within an isosteric series of chemicals. In this Table a variety of toxic end-points observed for benzene and naphthalene have been compared with those of their simple heterocyclic analogues, and it is clear that it is almost impossible to derive chemical structure-biological activity relationships from the published literature for even such a simple series of compounds. Even basic estimates of mammalian toxicity such as LD50 values cannot be accurately compared due either to the absence of relevant data or the noncomparability of those available. Thus in a field where there are little comparative data on the relative toxicity to mammals of pyrrole, thiophene and furan for example, it is difficult to relate chemical structure to biological activity in historical heterocyclic poisons such as strychnine (3) and hemlock [active agent coniine (4)]. 

Coniine, a toxic substance isolated from poison hemlock, contains only carbon, hydrogen, and nitrogen. Combustion analysis of a 5.024 mg sample yields 13.90 mg of C02 and 6.048 mg of H20. What is the empirical formula of coniine ... 

Several cyclic imines were reduced with phenylsilane as a reducing agent in the presence of the chiral titanocene catalyst 11 followed by a workup process to give the corresponding cyclic amines in excellent ee [26]. The hydrosilylation of 2-propyl-3,4,5,6-tetrahydropyridine with (R)-ll (substrate Ti=100 l) in THF at room temperature was completed in about 6 h (Scheme 14) [29]. The reaction mixture was treated with an acid and then with an aqueous base to afford (S)-coniine, the poisonous hemlock alkaloid, in 99% ee. 

The simple piperidine alkaloid coniine from poison hemlock is not derived from lysine, but originates by an animation process and is discussed on page 381. 

Several SM have been used by mankind for thousands of years22,27 as dyes (e.g., indigo, shikonine), flavors (e.g., vanillin, capsaicin, mustard oils), fragrances (e.g., rose oil, lavender oil and other essential oils), stimulants (e.g., caffeine, nicotine, ephedrine), hallucinogens (e.g., morphine, cocaine, mescaline, hyoscyamine, scopolamine, tetrahydrocannabinol), insecticides (e.g., nicotine, piperine, pyrethrin), vertebrate and human poisons (e.g., coniine, strychnine, aconitine) and even therapeutic agents (e.g., atropine, quinine, cardenolides, codeine, etc.). 

Alkaloids are widespread in plants and include some very well-known poisons (notably coniine and strychnine), hallucinogens (morphine, cocaine and muscimol) and other potentially lethal compounds that are nevertheless used in medical practice (e.g. atropine, codeine, colchicine and morphine). As indicated by the preliminary snap-shot above, alkaloids typically have names ending in -ine and which are often related to the plant source or properties. Thus, morphine was named after Morpheus (the God of sleep) and coniine derives from Conium maculatum (hemlock), the plant used in the judicial murder of Socrates (399 BC). Various chemical tests for alkaloids are used as preliminary indicators of alkaloid presence in crude plant extracts. Finally, it should be noted that alkaloids can also exist as jVoxides of the alkaloid base. 

Alkaloids which activate neuromuscular action (so-called parasympa-thomimetics) include nicotine, arecoline, physostigmine, coniine, cytisine, and sparteine. Inhibitory (or parasympatholytic) alkaloids include hyoscy-amine and scopolamine, (see above) 312). Skeletal muscles as well as muscle-containing organs, such as lungs, heart, circulatory system, and gut, and the nervous system are certainly very critical targets. The compounds are usually considered to be strong poisons, and it is obvious that... 

The natives of Peril were learning to ease their physical pains by chewing the leaves of coca shrub (Erytbroxylon tmxillence, "Rushy), which contain, among others, the alkaloid cocaine (11), and European citizens were recognizing other poisons such as coniine (12), from die poison hemlock ( Comum maculatum... 

Toxicity. Coniine is well absorbed from the gastro-intestinal tract and is very poisonous the estimated minimum lethal dose is 150 mg and toxic symptoms may occur after ingestion of 60 mg. Death may occur within 30 minutes or be delayed 3 to 12 hours. Coniine resembles nicotine in its peripheral action but produces more pronounced paralysis of the central nervous system and of the skeletal muscle nerve-endings. 

Z Coniine, C lpN. is the toxic prindpLc of the poison homlocV drunk by... 

Problem 9.6 A 1.50 g samj)le of coniine, the toxic extract of poison hemlock, was dissolved in... 

Coniine, is the toxic principle of the poison hemlock drunk... 

Coniine, a poisonous alkaloid isolated from the seeds, leaves, and roots of hemlock Conium maculatum), has been known since ancient times. Ingestion causes weakness, paralysis, and finally death. The Greek philosopher Socrates was executed by being forced to drink a potion prepared from hemlock in 339 b.c. 

Naturally occurring alkaloids—atropine from the poisonous nightshade plant, nicotine from tobacco, and coniine from hemlock (Section 25.6B)... 

Problem 9.S A 1.50 g sample of coniine, the toxic extract of poison hemlock, was dissolved in 10.0 mL of ethanol and placed in a sample cell with a 5.00 cm pathlength. The observed rotation at the sodium D line was +1.21°. Calculate lalp for coniine. 

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