Coniine
Title: Coniine
CAS Registry Number: 458-88-8
CAS Name: (2S)-2-Propylpiperidine
Additional Names: cicutine; conicine
Molecular Formula: C8H17N
Molecular Weight: 127.23
Percent Composition: C 75.52%, H 13.47%, N 11.01%
Literature References: Toxic principle of poison hemlock, Conium maculatum L., Umbelliferae: Ladenburg, Ber. 19, 439 (1886); Koller, Monatsh. Chem. 47, 393 (1926). Occurs naturally as the (S)-(+)-isomer. Review of early literature: Marion in The Alkaloids vol. I, R. H. F. Manske, H. L. Holmes, Eds. (Academic Press, New York, 1950) pp 211-217. Isoln from the pitcher plant, Sarracenia flava and insect paralyzing properties: N. V. Mody et al. Experientia 32, 829 (1976). Absolute configuration: J. C. Craig, S. K. Roy, Tetrahedron 21, 401 (1965). Resolution of (±)-form: J. C. Craig, A. R. Pinder, J. Org. Chem. 36, 3648 (1971). Synthesis of (S)-(+)-form: K. Aketa et al., Chem. Pharm. Bull. 24, 621 (1976); of (R)-(-)-form: D. Lathbury, T. Gallagher, Chem. Commun. 1986, 114; of (±)-form: T. Nagasaka et al., Heterocycles 27, 1685 (1988). Enantiospecific synthesis of (+)- and (-)-forms: L. Guerrier et al., J. Am. Chem. Soc. 105, 7754 (1983).
Properties: Colorless alkaline liquid, darkens and polymerizes on exposure to light and air. Mousy odor. mp ~-2°. bp 166-166.5°; bp20 65-66°. Volatile with steam. d420 0.844-0.848. nD23 1.4505. [a]D25 +8.4° (c = 4.0 in CHCl3); [a]D23 +14.6° (neat). pK 3.1. One ml dissolves in 90 ml water, less sol in hot water. The base dissolves about 25% water at room temp. Sol in alcohol, ether, acetone, benzene, amyl alcohol; slightly sol in chloroform.
Melting point: mp ~-2°
Boiling point: bp 166-166.5°; bp20 65-66°
pKa: pK 3.1
Optical Rotation: [a]D25 +8.4° (c = 4.0 in CHCl3); [a]D23 +14.6° (neat)
Index of refraction: nD23 1.4505
Density: d420 0.844-0.848
 
Derivative Type: Hydrobromide
CAS Registry Number: 637-49-0
Molecular Formula: C8H17N.HBr
Molecular Weight: 208.14
Percent Composition: C 46.16%, H 8.72%, N 6.73%, Br 38.39%
Properties: Prisms, mp 211°. One gram dissolves in 2 ml water, 3 ml alcohol; sol in chloroform, ether.
Melting point: mp 211°
 
Derivative Type: Hydrochloride
CAS Registry Number: 555-92-0
Molecular Formula: C8H17N.HCl
Molecular Weight: 163.69
Percent Composition: C 58.70%, H 11.08%, N 8.56%, Cl 21.66%
Properties: Rhomboids, mp 221°. Freely sol in water, alcohol, chloroform.
Melting point: mp 221°
 
Derivative Type: (R)-(-)-Form
Properties: Liquid, bp756 165°. [a]D25 -8.1° (c = 4.0 in CHCl3); [a]D23 -14.2° (neat).
Boiling point: bp756 165°
Optical Rotation: [a]D25 -8.1° (c = 4.0 in CHCl3); [a]D23 -14.2° (neat)
 
Derivative Type: (±)-Form
Properties: bp 200-210°.
Boiling point: bp 200-210°
 
CAUTION: Potential symptoms of overexposure include drowsiness, paresthesias, weakness, ataxia, nausea, profuse salivation, and bradycardia followed by tachycardia. See: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, pp 249-250.

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