Title: Strychnine
CAS Registry Number: 57-24-9
CAS Name: Strychnidin-10-one
Molecular Formula: C21H22N2O2
Molecular Weight: 334.41
Percent Composition: C 75.42%, H 6.63%, N 8.38%, O 9.57%
Literature References: Occurs most abundantly in seeds of Strychnos nux-vomica L., Loganiaceae and beans of S. ignatti, Berg. One of the first alkaloids isolated in pure form. Isoln: Pelletier, Caventou, Ann. Chim. Phys. 8, 323 (1818); ibid. 10, 142 (1819). Extraction procedure: C. Srinivasulu et al., Res. Ind. 23, 224 (1978). Structure elucidation: L. H. Briggs et al., J. Chem. Soc. 1946, 903; H. T. Openshaw, R. Robinson, Nature 157, 438 (1946); R. B. Woodward et al., J. Am. Chem. Soc. 69, 2250 (1947). Total synthesis: R. B. Woodward et al., ibid. 76, 4749 (1954); eidem, Tetrahedron 19, 247 (1963). Abs config: A. F. Peerdeman, Acta Crystallogr. 9, 824 (1956); K. Nagarajan et al., Helv. Chim. Acta 46, 1212 (1963). Stereoselective total synthesis: S. D. Knight et al., J. Am. Chem. Soc. 115, 9293 (1993). 1H- and 13C-NMR analysis: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978). Pharmacology and pharmacokinetics: S. Weiss, R. A. Hatcher, J. Pharmacol. Exp. Ther. 19, 419 (1921). Acute toxicity: I. Setnikar, M. J. Magistretti, Arzneim.-Forsch. 14, 996 (1964). HPLC determn in urine and tissues: T. Egloff et al., J. Clin. Chem. Clin. Biochem. 20, 203 (1982); GC/EI-MS determn in whole blood: M. Barroso et al., J. Chromatogr. B 816, 29 (2005). Review: J. B. Hendrickson in The Alkaloids vol. VI, R. H. F. Manske, Ed. (Academic Press, New York, 1960) pp 179-195; G. F. Smith, ibid. vol. VIII (1965) pp 591-671. Comprehensive description: F. J. Muhtadi, M. S. Hifnawy, Anal. Profiles Drug Subs. 15, 563-646 (1986). Brief review of synthesis: U. Beifuss, Angew. Chem. Int. Ed. 33, 1144-1149 (1994).
Properties: Brilliant, colorless cubes from chloroform-ether, mp 275-285°. d18 1.359. [a]D18 -104.3° (c = 0.254 in alc); [a]D25 -139° (c = 0.4 in chloroform). pKa (25°) 8.26: A. J. Everett et al., J. Chem. Soc. 1957, 1120. uv max (95% ethanol): 255, 280, 290 nm (E1%1 cm 377, 130, 101): A. I. Biggs, J. Pharm. Pharmacol. 13, 547 (1952). One gram dissolves in 182 ml ethanol, 6.5 ml chloroform, 150 ml benzene, 250 ml methanol, 83 ml pyridine; very slightly sol in ether, water. LD50 i.v. (slow infusion) in rats: 0.96 mg/kg (Setnikar, Magistretti).
Melting point: mp 275-285°
pKa: pKa (25°) 8.26: A. J. Everett et al., J. Chem. Soc. 1957, 1120
Optical Rotation: [a]D18 -104.3° (c = 0.254 in alc); [a]D25 -139° (c = 0.4 in chloroform)
Absorption maximum: uv max (95% ethanol): 255, 280, 290 nm (E1%1 cm 377, 130, 101): A. I. Biggs, J. Pharm. Pharmacol. 13, 547 (1952)
Density: d18 1.359
Toxicity data: LD50 i.v. (slow infusion) in rats: 0.96 mg/kg (Setnikar, Magistretti)
Derivative Type: Hydrochloride dihydrate
CAS Registry Number: 6101-04-8
Molecular Formula: C21H22N2O2.HCl.2H2O
Molecular Weight: 406.90
Percent Composition: C 61.99%, H 6.69%, N 6.88%, O 15.73%, Cl 8.71%
Properties: Efflorescent, trimetric prisms. One gram dissolves in ~35 ml cold water, ~80 ml alc. Insol in ether. pH of 0.01M soln 5.4.
Derivative Type: Nitrate
CAS Registry Number: 66-32-0
Molecular Formula: C21H22N2O2.HNO3
Properties: Colorless, odorless needles or white, cryst powder. At 25°, one gram dissolves in 42 ml water, 120 ml alcohol, 156 ml chloroform. Insol in ether. pH ~5.7. Protect from light.
Derivative Type: Sulfate
CAS Registry Number: 60-41-3
Molecular Formula: (C21H22N2O2)2.H2SO4
Properties: Usually crystallizes as pentahydrate. Properties of pentahydrate: colorless, odorless, very bitter crystals, or white, cryst powder. Effloresces in dry air; loses all its water of crystn at 100°. mp when anhydr ~200° with decompn. At 25°, one gram dissolves in 31 ml water, 65 ml alcohol, 325 ml chloroform. Insol in ether. pH 5.5 in 1:100 soln. Protect from light. LD50 orally in rats: 5 mg/kg, E. W. Schafer, Toxicol. Appl. Pharmacol. 21, 315 (1972).
Melting point: mp when anhydr ~200° with decompn
Toxicity data: LD50 orally in rats: 5 mg/kg, E. W. Schafer, Toxicol. Appl. Pharmacol. 21, 315 (1972)
CAUTION: Extremely poisonous, see: G. D. Osweiler, Curr. Vet. Ther. 6, 115 (1977). Potential symptoms of overexposure to strychnine are stiff neck and facial muscles; restlessness, apprehension and increased acuity of perception; increased reflex excitability; cyanosis; tetanic convulsions with opisthotonos. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 286.
Use: Chiefly in poison baits for rodents.
Therap-Cat-Vet: Has been used as a tonic and central stimulant. |