Strychnine

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Strychnine
Strychnine salt bottle sample formula by Thy Labs.jpg
Strychnine sample
Names
IUPAC name
Strychnidin-10-one
Systematic IUPAC name
(4bR,4b1S,7aS,8aR,8a1R,12aS)-4b1,5,6,7a,8,8a,8a1,11,12a,13-Decahydro-14H-12-oxa-7,14a-diaza-7,9-methanocyclohepta[cd]cyclopenta[g]fluoranthen-14-one
Other names
(-)-Strychnine
Properties
C21H22N2O2
Molar mass 334.419 g/mol
Appearance White crystalline solid
Odor Odorless
Density 1.359 g/cm3[1]
Melting point 265–270 °C (509–518 °F; 538–543 K) [8]
Boiling point 284–286 °C (543–547 °F; 557–559 K) (decomposes)
0.014 g/100 ml (20 °C)
0.016 g/100 ml (25 °C)
0.060 g/100 ml (75 °C)[2][3]
Solubility Soluble in aniline, chloroform
Slightly soluble in amyl alcohol, benzene, carbon tetrachloride, ethanol, piperidine, pyridine
Almost insoluble in diethyl ether, petroleum ether
Solubility in acetone 0.167 g/100 g (15 °C)[4]
Solubility in aniline 20 g/100 ml (20 °C)[5]
Solubility in carbon tetrachloride 0.26 g/100 ml (15 °C)[6]
Solubility in chloroform 10.25 g/100 g (20 °C)[7]
Solubility in dimethylamine 1.7 g/100 g (20 °C)[5]
Vapor pressure ~0 mmHg
Hazards
Safety data sheet Sigma-Aldrich
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
0.5 mg/kg (dog, oral)
0.5 mg/kg (cat, oral)
2 mg/kg (mouse, oral)
16 mg/kg (rat, oral)
2.35 mg/kg (rat, oral)
5-120 (man, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Strychnine is a highly toxic, colorless, bitter, natural-occuring alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. It is one of the first alkaloids isolated in pure form.

Properties

Chemical

Strychnine is sensitive to strong oxidizers.

Physical

Strychnine is a colorless or white crystalline solid, almost insoluble in water, but more soluble in some organic solvents.

Solubility of freebase strychnine in various organic solvents:

  • Amyl alcohol: 0.55 g/100 g (25 °C)[9]
  • Benzene: 0.77 g/100 g (20 °C)[10]
  • Diethyl ether: 0.018 g/100 g (25 °C)[10]
  • Ethanol: 0.7 g/100 g (25 °C)[11]
  • Ethyl acetate: 0.197 g/100 g (20 °C)[10]
  • Glycerol: 0.25 g/100 g (15 °C)[12]
  • Methanol: 0.49 g/100 g (25 °C)[11]
  • p-Cymene: 0.71 g/100 g (30 °C); 0.95 g/100 g (100 °C)[13]
  • Petroleum ether: 0.0093 g/100 g (20 °C)[10]
  • Piperidine: 0.7 g/100 g (20 °C)[5]

Availability

Strychnine occurs naturally in the seeds of Strychnos nux-vomica and Icaja, Loganiaceae, as well as beans of S. ignatti, and can be extracted from the plant material using organic solvents.[14] Seeds contain around 1.5% strychnine by dry mass and the dried blossoms contain 1.0%.[15] Bark of the Strychnos tree also contains strychnine, as well as brucine,with the percentage of each alkaloid varying, depending on the part of the plant: 1.7% and 2.8% in root bark, 0.3% and 0.4% in root-wood, 0.9% and 2.1% in stem-bark, 0.5% and 0.01% in stem-wood, and 0.2% and 0.5% in leaves, respectively.[16]

Strychnine is sold by chemical suppliers, either as nitrate salt or as freebase. Due to its high toxicity, most companies will not sell it to private individuals and in some countries possession of such substance may be illegal. In Brazil, for example, strychnine is included in Class F4 under the Brazilian Controlled Drugs and Substances Act.

Preparation

Total synthesis of strychnine has been described several times in literature.[17][18][19]

Projects

  • Compound collecting

Handling

Safety

Strychnine is highly toxic, but due to its extremely bitter taste, it's difficult to absorb a large amount of poison by ingestion alone. Inhalation and injection are an easier way of absorbing higher doses. In high doses, strychnine is very toxic to humans (minimum lethal oral dose in adults is 30–120 mg) and many other animals (oral LD50 = 16 mg/kg in rats, 2 mg/kg in mice), and poisoning by inhalation, swallowing, or absorption through eyes or mouth can be fatal.

The first symptoms to appear are generalized muscle spasms, which can appear after 5-15 minutes of absorption. With a very high dose, the onset of respiratory failure and brain death can occur in 15 to 30 minutes. If a lower dose is ingested, other symptoms begin to develop, including seizures, cramping, stiffness, hypervigilance, and agitation. Seizures caused by strychnine poisoning can start as early as 15 minutes after exposure and last 12–24 hours.

There is no specific antidote for strychnine but recovery from exposure is possible with early supportive medical treatment. Strychnine poisoning demands aggressive management with early control of muscle spasms, intubation for loss of airway control, toxin removal (decontamination), intravenous hydration and potentially active cooling efforts in the context of hyperthermia as well as hemodialysis in kidney failure.

Storage

Should be kept in closed bottles, in a locked cabinet or safe. Ampouling is a good option for storing the compound.

Disposal

Strychnine can be destroyed by using a strong oxidizer, like bleach, then the resulting product must be diluted in water and can be poured down the drain or into the ground.

References

  1. ↑ Clarke; Chemische Berichte; vol. 12; (1879); p. 1399
  2. ↑ Ng; Poe; Journal of the American Pharmaceutical Association (1912-1977); vol. 45; (1956); p. 351
  3. ↑ Gupta R.C. Handbook of Toxicology of Chemical Warfare Agents. - Elsevier, 2009
  4. ↑ Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
  5. ↑ 5.0 5.1 5.2 Scholtz; Archiv der Pharmazie (Weinheim, Germany); vol. 250; (1912); p. 423
  6. ↑ Dott; Pharmaceutical Journal; vol. 140; (1938); p. 357
  7. ↑ Dhar; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 155; (1926); p. 46
  8. ↑ Kaburagi, Yosuke; Tokuyama, Hidetoshi; Fukuyama, Tohru; Journal of the American Chemical Society; vol. 126; nb. 33; (2004); p. 10246 - 10247
  9. ↑ Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941
  10. ↑ 10.0 10.1 10.2 10.3 Beckurts; Mueller; Apoth.-Ztg.; vol. 18; p. 257; Chem. Zentralbl.; vol. 74; nb. I; (1903); p. 1142
  11. ↑ 11.0 11.1 Schaefer; American Journal of Pharmacy and the Sciences Supporting Public Health (1937-1978); vol. 85; (1913); p. 441; Chem. Zentralbl.; vol. 84; nb. II; (1913); p. 1828
  12. ↑ Solubility Handbook. - T.1, Book.2. - M.-L.: IAN USSR, 1962 (Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962)
  13. ↑ Wheeler; Journal of the American Chemical Society; vol. 42; (1920); p. 1844
  14. ↑ C. Srinivasulu et al., Res. Ind. 23, 224 (1978)
  15. ↑ Fu, Yanhui; Zhang, Yu; He, Hongping; Hou, Li; Di, Yingtong; Li, Shunlin; Luo, Xiaodong; Hao, Xiaojiang; Journal of Natural Products; vol. 75; nb. 11; (2012); p. 1987 - 1990
  16. ↑ Tchinda, Alembert T.; Tamze, Victorine; Ngono, Annie R.N.; Ayimele, Godfred A.; Cao, Martine; Angenot, Luc; Frederich, Michel; Phytochemistry Letters; vol. 5; nb. 1; (2012); p. 108 - 113,
  17. ↑ R. B. Woodward et al., ibid. 76, 4749 (1954)
  18. ↑ Tetrahedron 19, 247 (1963)
  19. ↑ S. D. Knight et al., J. Am. Chem. Soc. 115, 9293 (1993)

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