strychnine

[French, from New Latin Strychnos, genus name, from Latin strychnon, a kind of nightshade, from Greek strukhnon.]

A colourless poisonous crystalline alkaloid found in certain plants.

For more information on strychnine, visit Britannica.com.

An alkaloid drug obtained from the seeds of Strychnos nux-vomica. In high doses, strychnine causes severe muscular spasms which can be fatal if respiratory muscles are involved. In low doses it can act as a stimulant, boosting athletic performance. A related chemical was used by the Aztecs to enable them to complete their amazing runs which lasted up to 3 days. In the nineteenth century and the early part of this century, disreputable trainers and coaches sometimes spiked the drinks of their charges with small amounts of strychnine to give them an extra boost during very demanding competitions, such as bare-knuckle fights. In the St. Louis Olympic Games of 1904, the marathon runner, Thomas Hicks, was given strychnine mixed with brandy, in order to inject a bit more pace into his last few kilometres of running.

An alkaloid drug belonging to the stimulants. Strychnine is obtained from seeds of Trychnos nuxvomica and was formerly used in small amounts in ‘tonics’. The drug blocks the action of glycine. High doses cause muscular spasms similar to those resulting from tetanus; death can occur due to spasms of the respiratory muscles.

A very poisonous alkaloid from seeds of the plant Strychnos nux-vomica and other species of Strychnos. A commonly used compound in malicious poisoning of dogs and used as a feral animal bait to which domestic dogs find access. The dogs may also be poisoned by eating the vermin. Clinical findings include tetanic convulsions especially in response to external stimuli.

Tutor's tip: This word was used in the 2006 Scripps National Spelling Bee finals.

Strychnine
Other names	Strychnidin-10-one
Identifiers
CAS number	57-24-9 Y
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
Y (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 = 10 mg approx.), 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 1 Pharmacology 2 History 3 See also 4 References

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.^{[citation needed]}

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

• Avicide
• Strychnine poisoning
• The Mysterious Affair at Styles
• Wieland-Gumlich aldehyde
• Denatonium

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. 

v • d • e Pest control: rodenticides Anticoagulants/ vitamin K antagonists coumarins/4-Hydroxycoumarins: 1st generation (Warfarin, Coumatetralyl) • 2nd generation (Brodifacoum, Difenacoum, Flocoumafen) 1,3-Indandiones: Chlorophacinone • Pindone • Diphacinone other: Difethialone Convulsants Crimidine • Phenylsilatrane • Strychnine • Tetramethylenedisulfotetramine Calciferols Cholecalciferol • Ergocalciferol Inorganic compounds Aluminium phosphide • Arsenic • Barium carbonate • Calcium phosphide • Cyanide • Thallium • Zinc phosphide Organochlorine Chloralose • Endrin Organophosphorus Phosacetim Metabolic poisons Bromethalin • Fluoroacetamide • 1,3-Difluoro-2-propanol (Gliftor) • Sodium fluoroacetate Other α-Naphthylthiourea • Norbormide • Pyrinuron • Scilliroside

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Dansk (Danish)
n. - stryknin

Nederlands (Dutch)
strychnine

Français (French)
n. - strychnine

Deutsch (German)
n. - Strychnin

Ελληνική (Greek)
n. - (χημ.) στρυχνίνη

Italiano (Italian)
stricnina

Português (Portuguese)
n. - estricnina (f)

Русский (Russian)
рвотный корень, стрихнин

Español (Spanish)
n. - estricnina

Svenska (Swedish)
n. - strykning

中文（简体）(Chinese (Simplified))
士的宁, 番木鳖碱

中文（繁體）(Chinese (Traditional))
n. - 士的寧, 番木鱉堿

한국어 (Korean)
n. - 스트리크닌, 중추 신경 흥분제

日本語 (Japanese)
n. - ストリキニーネ

العربيه (Arabic)
‏(الاسم) مادة الستركنين السامه‏

עברית (Hebrew)
n. - ‮סטריכנין‬

If you are unable to view some languages clearly, click here.

To select your translation preferences click here.