Title: Chanoclavine
CAS Registry Number: 2390-99-0
CAS Name: [4R-[4a,5b(E)]]-2-Methyl-3-[1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-2-propen-1-ol
Additional Names: (E)-8,9-didehydro-6-methyl-6,7-secoergoline-8-methanol; chanoclavin-I; secaclavine
Molecular Formula: C16H20N2O
Molecular Weight: 256.34
Percent Composition: C 74.97%, H 7.86%, N 10.93%, O 6.24%
Literature References: Precursor of the tetracyclic ergolines, agroclavine, elymoclavine, and lysergic acid amide, q.q.v.: Gröger et al., Z. Naturforsch. 21b, 827 (1966); Floss et al., Chem. Commun. 1967, 105. Occurs in sclerotia of Claviceps purpurea (Fries) Tul., Hypocreaceae, in Ipomea tricolor Cav., Convolvulaceae and is one of the active principles of the ancient Aztec drug "Ololiuqui," Rivea coryrubosa (L.) Hall. f., Convolvulaceae: Hofmann, Tscherter, Experientia 16, 414 (1960). Isoln and structure: Hofmann et al., Helv. Chim. Acta 40, 1358 (1957). Isoln of stereoisomers: Stauffacher, Tscherter, ibid. 47, 2186 (1964). Stereochemistry: Acklin et al., Chem. Commun. 1966, 799. Biosynthetic studies: Floss et al., J. Am. Chem. Soc. 90, 6500 (1968). Total synthesis of (±)-chanoclavine: H. Plieninger et al., Tetrahedron Lett. 1975, 1827; H. Plieninger, D. Schmalz, Ber. 109, 2140 (1976); M. Natsume, H. Muratake, Heterocycles 16, 375 (1981).
Properties: Thick prisms and polyhedra from acetone or methanol, mp 220-222°. [a]D20 -240° (pyridine), [a]D20 -205° (c = 0.75 in alcohol). uv max: 225, 284, 293 nm (e 4.44, 3.82, 3.72). One gram dissolves in 25 ml boiling methanol, 140 ml boiling acetone, 170 ml boiling ethyl acetate or 350 ml boiling chloroform. Practically insol in water.
Melting point: mp 220-222°
Optical Rotation: [a]D20 -240° (pyridine); [a]D20 -205° (c = 0.75 in alcohol)
Absorption maximum: uv max: 225, 284, 293 nm (e 4.44, 3.82, 3.72)
Derivative Type: Epimer at position 10
Additional Names: Chanoclavine II
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