165. Adlumidine

Nomenclature

CAS number: 550-49-2
(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.
C20H17NO6; mol wt 367.35.
C 65.39%, H 4.66%, N 3.81%, O 26.13%.

Description and 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.

Chemical structure

Properties

Rhombic plates from chloroform + methanol, mp 236-237°. [α]D25 +116.2° (c = 22 in chloroform). pKa 4.27. Practically insol in water. Very sparingly sol in alcohol, ether, hexane.

Derivative

l-Adlumidine.

Nomenclature

CAS number: 485-50-7
Capnoidine.

Properties

Stout prisms from chloroform + methanol, mp 238°. [α]D22 113.2° (in chloroform). pKa 4.24. Practically insol in water. Sparingly sol in methanol; sol in chloroform.