Nomenclature
CAS number: 458-88-8
(2
S)-2-Propylpiperidine; cicutine; conicine.
C
8H
17N; mol wt 127.23.
C 75.52%, H 13.47%, N 11.01%.
Description and 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. [α]D25 +8.4° (c = 4.0 in CHCl3); [α]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.Derivative
Hydrobromide.
Nomenclature
CAS number: 637-49-0
C
8H
17N.HBr; mol wt 208.14.
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.Derivative
Hydrochloride.
Nomenclature
CAS number: 555-92-0
C
8H
17N.HCl; mol wt 163.69.
C 58.70%, H 11.08%, N 8.56%, Cl 21.66%.
Properties
Rhomboids, mp 221°. Freely sol in water, alcohol, chloroform.Derivative
(R)-(-)-Form.
Properties
Liquid, bp756 165°. [α]D25 -8.1° (c = 4.0 in CHCl3); [α]D23 -14.2° (neat).Derivative
(±)-Form.
Properties
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.