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Strychnine
Strychnine2.svg
Strychnine-from-xtal-3D-balls.png
Other names Strychnidin-10-one
Identifiers
CAS number 57-24-9 Yes check.svgY
PubChem 441071
SMILES
Properties
Molecular formula C21H22N2O2
Molar mass 334.41
Melting point

284-286 °C

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Strychnine (pronounced /ˈstrɪkniːn/; also US: /ˈstrɪknaɪn/ or /ˈstrɪknɪn/) is a very toxic (LD50 = c. 10 mg/kg), colorless crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions and eventually death through asphyxia or sheer exhaustion. The most common source is from the seeds of the Strychnos nux vomica tree. Strychnine is one of the most bitter substances known. Its taste is detectable in concentrations as low as 1 ppm.

Contents

Pharmacology

Strychnine acts as a blocker or antagonist at the inhibitory or strychnine-sensitive glycine receptor (GlyR), a ligand-gated chloride channel in the spinal cord and the brain.[1]

Although it is best known as a poison, small doses of strychnine were once used in medications as a stimulant, as a laxative, and as a treatment for other stomach ailments. A 1934 drug guide for nurses described it as "among the most valuable and widely prescribed drugs".[2] Strychnine's stimulant effects also led to its use historically for enhancing performance in sports.[3] Because of its high toxicity and tendency to cause convulsions, the use of strychnine in medicine was eventually abandoned once safer alternatives became available.

The dosage for medical use was cited as between "1/60th grain–1/10th grain", which is between 1.1 milligrams and 6.4 milligrams in modern measures. In normal circumstances, the maximum dosage used was 3.2 mg, half of a "full dose".[4] A lethal dose was cited as 1/2 a grain (32 mg), but people have been known to die from as little as 5 mg of strychnine.

History

Strychnine was first isolated from the beans of Strychnos ignatii by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818. Its structure was determined by Sir Robert Robinson and Herman Leuchs in 1946. In 1952, Robinson wrote that "For its molecular size it is the most complex substance known."[5]

The first total synthesis of this molecule was reported by R. B. Woodward and his coworkers in 1954 (see: strychnine total synthesis).[6] X-ray crystallography studies confirmed the natural configuration of the molecule in 1956.[5] In 1963, a complete paper was published by Woodward and his coworkers.[7] [8] K. C. Nicolaou calls the published synthesis "a spectacular achievement of organic synthesis".[5] Other syntheses have been published.[9] [10]

See also

References

  1. ^ Purves, Dale, George J. Augustine, David Fitzpatrick, William C. Hall, Anthony-Samuel LaMantia, James O. McNamara, and Leonard E. White (2008). Neuroscience. 4th ed.. Sinauer Associates. pp. 137–8. ISBN 978-0-87893-697-7.  
  2. ^ Principal Drugs and Their Uses, A.L. Morton, Faber and Faber, London, 1934
  3. ^ Performance-Enhancing Substances in Sport and Exercise, Michael S. Bahrke and Charles Yesalis, Human Kinetics, 2002, ISBN 0736036792 Google Books
  4. ^ Nux Vomica. | Henriette's Herbal Homepage
  5. ^ a b c Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. pp. 21, 40. ISBN 3-527-29284-5.  
  6. ^ R. B. Woodward, Michael P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker (1954). "The total synthesis of strychnine". J. Am. Chem. Soc. 76: 4749. doi:10.1021/ja01647a088.  
  7. ^ R. B. Woodward, Michael P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker (1963). "The total synthesis of strychnine". Tetrahedron 19: 247.  
  8. ^ "Woodward Synthesis of Strychnine". http://www.chem.wisc.edu/areas/reich/syntheses/Strychnine-Woodward-syn.htm.  
  9. ^ "Overman Synthesis of Strychnine". http://www.chem.wisc.edu/areas/reich/syntheses/Strychnine-Overman-syn.htm.  
  10. ^ "Shibasaki Synthesis of Strychnine". http://www.chem.wisc.edu/areas/reich/syntheses/Strychnine-Shibasaki-syn.htm.  

1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

'STRYCHNINE, C21H22N202, an alkaloid discovered in 1818 by Pelletier and Caventou in St Ignatius's beans (Strychnos Ignatii); it also occurs in other species of Strychnos, e.g. S. Nux vomica, S. colubrina, S. Tieute, and is generally accompanied by another alkaloid brucine, C23H26N204 41I 2 O, which was isolated by Pelletier and Caventou in 1819. Strychnine crystallizes from alcohol in colourless prisms, which are practically insoluble in water, and with difficulty soluble in the common organic solvents. Its taste is exceptionally bitter. It has an alkaline reaction, and is a tertiary monacid base. It is optically active, the natural form being laevorotatory. Brucine closely resembles strychnine, and is its dimethoxy derivative. The constitutions are unknown '(see J. Schmidt, Die Alkaloidchemie, 1904; 1909).

Table of contents

Medicine

The B.P. dose of strychnine is to gr. in solution or in pill form. A preparation is syrupus ferri phosphatis cum quinina et strychnine, containing gr. of strychnine in each fluid drachm. Strychninae hydrochloridum is also used; it is much more soluble than strychnine. From it is prepared liquor strychninae hydrochloridi, containing 1 gr. of hydrochloride in i io minims. The United States pharmacopoeia also contains strychninae nitras and strychninae sulphas. Strychnine is incompatible with liquor arsenicalis and potassium iodide.

Physiological Action

Applied externally strychnine is a powerful antiseptic, but its poisonous nature prevents it from being used for this purpose. Brucine is a local anaesthetic. Strychnine enters the blood as such, being freely absorbed from mucous surfaces or when given hypodermically. Internally strychnine acts as a bitter, increasing the secretion of gastric juice and the intestinal peristalsis, being a direct stimulant to the muscular coat; in this manner it has a purgative action. The specific effects of the drug, however, are upon the central nervous system. It excites the motor areas of the spinal cord and increases their reflex irritability. Small doses increase the sensibility of touch, sight and hearing; large doses cause twitching of the muscles and difficulty in swallowing; while in overdose violent convulsions are produced. The cerebral convolutions remain unaffected, but the important centres of the medulla oblongata are stimulated. Not only is the respiratory centre stimulated but the cardiac centre is acted upon both directly by the drug and indirectly for a time by the enormous rise in blood pressure due to the contraction of the arterioles all over the body. Ordinary doses have no effect upon the temperature but in overdose the temperature rises during a convulsion. Strychnine is eliminated by the kidneys as strychnine and strychnic acid. It is excreted very slowly and therefore accumulates in the system.

Therapeutics

Strychnine is chiefly used as a stimulant. It is indicated in paralyses (chiefly functional), and is most valuable in the treatment of post-diphtheritic paralysis. In progressive lead palsy, beri-beri, and the paralysis following acute alcoholism, fairly large doses are useful. In pneumonia and other acute disease, where the patient is liable to sudden collapse, a hypodermic injection of strychnine will often save the patient's life. In ccllapse following severe haemorrhage and in sudden and accidental arrest of the heart or respiration during chloroform narcosis an intramuscular injection of 1 gr. of the hydrochloride may stimulate the cardiac action. In acute opium poisoning strychnine is very valuable. It is a physiological antagonist of chloral hydrate, morphine and physostigmine, and may be given in poisoning by these drugs. In dyspnoea due to emphysema, phthisis and asthma, strychnine is of service, given internally in doses of i to 3 minims of the liquor. The syrup of iron, quinine and strychnine is used as a tonic.

Toxicology

The symptoms of strychnine poisoning usually appear within twenty minutes of the ingestion of a poisonous dose, starting with an uneasy sensation, stiffness at the back of the neck, twitching of the muscles and a feeling of impending suffocation. The patient is then seized with violent convulsions of a tetanic character; the arms are stretched out, respiration impeded, the muscles are rigid, the body is thrown into opisthotonos, i.e. it rests bowform on the head and the heels (occasionally the body is flexed forward [emprosthotonos], the eyes remain wide open and fixed, and the mouth is drawn aside (rises sardonicus). After a minute the muscles relax, and the patient sinks back exhausted, consciousness being preserved throughout. Any noise, a draught of air or a touch may cause a convulsion. If the case is about to terminate fatally the spasms rapidly succeed each other and death usually occurs within two hours, either from asphyxia produced by spasm of the respiratory muscles or more rarely from exhaustion. After death the position of the body may or may not be flexed; usually rigor mortis develops rapidly. In cases which recover the convulsions diminish in severity, leaving the patient exhausted. - Complications are infrequent. The average fatal dose for an adult is i 2 grs., but death has resulted in twenty minutes from 2 grain. On the other hand, recovery has taken place after 5 and to and even 20 grains have been swallowed, but in the latter case an emetic was at once administered. Idiosyncrasy plays a considerable part in determining the effects, some people being particularly susceptible; death has occurred in five minutes from the appearance of the first symptoms, but when a narcotic has been administered at the same time as the poison the development is proportionately slow. Tetanus resembles strychnine poisoning, but the development of the symptoms in tetanus is usually much slower, death rarely occurring within 24 hours. In strychnine poisoning trismus or lockjaw is generally secondary to spasm of the other muscles, while in tetanus it is usually the first symptom, no relaxation taking place between the spasms.

The treatment of strychnine poisoning is to immediately evacuate the stomach with a stomach-pump or emetic, chloroform being administered to allay the spasms. If the patient can swallow, draughts of water containing tannic acid may be given. Nitrite of amyl inhalations are useful in the early stages when the respiratory muscles are freely movable. Chloral and potassium bromide may be given as physiological antidotes. If death from asphyxia appears imminent artificial respiration may be resorted to.


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Simple English

Strychnine
Other names Strychnidin-10-one
Identifiers
CAS number 57-24-9
PubChem 441071
SMILES [H][C@]([C@@](C(C=CC=C7)
=C7N34)5[C@H]6N(CC5)C2)3
[C@@]1([H])[C@@H](C6)[C@]
2=CCO[C@H]1CC4=O
Properties
Molecular formula C21H22N2O2
Molar mass 334.41
Melting point

284-286 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Strychnine (pronounced /ˈstrɪkniːn/ (British, U.S.), /-naɪn/ or /-nɪn/ (U.S.)) is a very toxic colorless crystalline alkaloid. It is very poisonous, the LD50 is about 10 mg. Strychnine is soluble in alcohol and chloroform, but not in water.

Strychnine can act as a stimulant, much like caffeine. It is on the list of substances tested for doping in sports.

The substance was used as a pesticide, especially for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions. It leads to death through asphyxia or exhaustion. The most common source is from the seeds of the Strychnos nux vomica tree. Strychnine is one of the most bitter substances known. Its taste is detectable in concentrations as low as 1 ppm.

Poisoning

Between 30 and 120mg can kill an adult human. Strychnine is rapidly absorbed by Mucous membranes. If its given under the skin, or intravenously, a quantity of 15 mg may be enough to kill an adult. Benzodiazepines (such as Diazepam) are used by default for emergency treatment.

Unlike the illustrations given in fiction crime novels, Strychnine is not very good for killing someone (when given orally). This is because even diluted at 1:130.000 it can still be tasted. Despite this, some murders happened with Strychnine. Thomas Neill Cream, a serial killer used it on some of his victims.

Pharmacology

Strychnine acts as a blocker or antagonist at the inhibitory or strychnine-sensitive glycine receptor (GlyR), a ligand-gated chloride channel in the spinal cord and the brain.

Although it is best known as a poison, small doses of strychnine were once used in medications as a stimulant, a laxative and as a treatment for other stomach ailments. A 1934 drug guide for nurses described it as "among the most valuable and widely prescribed drugs".[1] Strychnine's stimulant effects also led to its use historically for enhancing performance in sports.[2] Because of its high toxicity and tendency to cause convulsions, the use of strychnine in medicine was eventually abandoned once safer alternatives became available.

The dosage for medical use was cited as between "1/60th grain–1/10th grain", which is between 1.1 milligrams and 6.4 milligrams in modern measures. Normally the maximum dosage used was 3.2 mg, half of a "full dose".[3] A lethal dose was cited as 1/2 a grain (32 mg), but people have been known to die from as little as 5 mg of strychnine.

References

  1. Principal Drugs and Their Uses, A.L. Morton, Faber and Faber, London, 1934
  2. Performance-Enhancing Substances in Sport and Exercise, Michael S. Bahrke and Charles Yesalis, Human Kinetics, 2002, ISBN 0-7360-3679-2 Google Books
  3. Nux Vomica. | Henriette's Herbal Homepage







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