Title: Loline
CAS Registry Number: 25161-91-5
CAS Name: [2R-(2a,3a,3ab,4a,6ab)]-Hexahydro-N-methyl-2,4-methano-4H-furo[3,2-b]pyrrol-3-amine
Additional Names: festucine; methyl-N-depropionyldecorticasine
Molecular Formula: C8H14N2O
Molecular Weight: 154.21
Percent Composition: C 62.31%, H 9.15%, N 18.17%, O 10.38%
Literature References: One of a group of pyrrolizidine alkaloids whose common feature is a unique oxygen bridge. Isoln from seeds of Lolium cuneatum Nevski, Gramineae: S. Y. Yunusov, S. T. Akramov, J. Gen. Chem. USSR 25, 1765 (1955); from tall fescue hay, Festuca arundinaceae Schreb., Gramineae: Yates, Tookey, Aust. J. Chem. 18, 53 (1965). Identity with festucine: Aasen, Culvenor, ibid. 22, 2021 (1969). Identity with methyl-N-depropionyldecorticasine: Ribas et al., An. Quim. 64, 516 (1968), C.A. 69, 109764c (1968). Abs config: R. B. Bates, S. R. Morehead, Tetrahedron Lett. 1972, 1629. Synthesis of bisquaternary salts: N. P. Abdullaev et al., Khim. Prir. Soedin. 3, 371 (1977), C.A. 88, 23216 (1978). Synthetic and structural studies: S. R. Wilson et al., J. Org. Chem. 46, 3887 (1981).
Derivative Type: Dihydrochloride
Molecular Formula: C8H14N2O.2HCl
Molecular Weight: 227.13
Percent Composition: C 42.30%, H 7.10%, N 12.33%, O 7.04%, Cl 31.22%
Properties: Needles from abs ethanol, dec 237-242°. [a]D25 +4.6° (c = 4.37 in water). pKa 8.25 and 2.5-3.0.
pKa: pKa 8.25 and 2.5-3.0
Optical Rotation: [a]D25 +4.6° (c = 4.37 in water)
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