Title: Adlumidine
CAS Registry Number: 550-49-2
CAS Name: (6S)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
Molecular Formula: C20H17NO6
Molecular Weight: 367.35
Percent Composition: C 65.39%, H 4.66%, N 3.81%, O 26.13%
Literature References: An alkaloid present in the d-form in the entire plant of Adlumia fungosa (Ait.) Greene (A. cirrhosa Raf.), Corydalis thalictrifolia Franch. and C. incisa (Thumb.) Pers., Fumariaceae. Schlotterbeck, Watkins, J. Am. Chem. Soc. 25, 596 (1903); R. H. F. Manske, Can. J. Res. 21B, 111 (1943). l-Adlumidine was isolated from Corydalis sempervirens (L.) Pers., C. scouleri Hook., and C. crystallina Engelm., Fumariaceae: R. H. F. Manske, ibid. 8, 407 (1932); 14B, 347 (1936); 17B, 57 (1939). Structure: idem, J. Am. Chem. Soc. 72, 3207 (1950). Stereochemistry: Blaha et al., Collect. Czech. Chem. Commun. 29, 2328 (1964); Snatzke et al., Tetrahedron 25, 5059 (1969). Review: Stanek, Manske in The Alkaloids vol. IV, R. H. F. Manske, H. L. Holmes, Eds. (Academic Press, New York, 1954) pp 167-198. Stereoisomer of bicuculline, q.v.
Properties: Rhombic plates from chloroform + methanol, mp 236-237°. [a]D25 +116.2° (c = 22 in chloroform). pKa 4.27. Practically insol in water. Very sparingly sol in alcohol, ether, hexane.
Melting point: mp 236-237°
pKa: pKa 4.27
Optical Rotation: [a]D25 +116.2° (c = 22 in chloroform)
Derivative Type: l-Adlumidine
CAS Registry Number: 485-50-7
Additional Names: Capnoidine
Properties: Stout prisms from chloroform + methanol, mp 238°. [a]D22 -113.2° (in chloroform). pKa 4.24. Practically insol in water. Sparingly sol in methanol; sol in chloroform.
Melting point: mp 238°
pKa: pKa 4.24
Optical Rotation: [a]D22 -113.2° (in chloroform)
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