Lupanine
Title: Lupanine
CAS Name: (7a,7aa,14a,14ab)-Dodecahydro-7,14-methano-2H,11H-dipyrido[1,2-a:1¢,2¢-e][1,5]diazocin-11-one
Additional Names: dodecahydro-7,14-methano-4H,6H-dipyrido[1,2-a:1¢,2¢-e][1,5]diazocin-4-one
Molecular Formula: C15H24N2O
Molecular Weight: 248.36
Percent Composition: C 72.54%, H 9.74%, N 11.28%, O 6.44%
Literature References: Racemic lupanine is found in white lupins, d-lupanine is found in blue lupins, l-lupanine has been prepd from the natural racemic form. Structure: Davis, Arch. Pharm. 235, 199, 218, 229 (1897); Clemo, Leitch, J. Chem. Soc. 1928, 1811; Clemo et al., ibid. 1931, 429; 1933, 644; Ing, ibid. 1933, 504; Karrer et al., Helv. Chim. Acta 11, 1062 (1928), 13, 1292 (1930); Winterfeld, Holschneider, Ber. 64, 137, 2415 (1931), 66, 1751 (1933); Ann. 499, 109 (1932); Winterfeld, Kneuer, Ber. 64, 150 (1931); Winterfeld, Hoffman, Arch. Pharm. 275, 5, 65 (1937). Abs config of l-form: Okuda et al., Chem. Ind. (London) 1961, 1116. Crystal structure of dl-form: H. Doucerain et al., Acta Crystallogr. B32, 3213 (1976). Biosynthetic study of d-form: W. M. Golebewski, I. D. Spenser, J. Am. Chem. Soc. 106, 7925 (1984). See also sparteine, q.v.
 
Derivative Type: dl-Form
CAS Registry Number: 4356-43-8
Properties: Orthorhombic prisms from acetone, mp 98-99°. bp1.0 185-195°. Sol in water, alcohol, ether, chloroform. Insol in petr ether. See: Soldaini, Arch. Pharm. 231, 321 (1893); Couch, J. Am. Chem. Soc. 56, 1423 (1934).
Melting point: mp 98-99°
Boiling point: bp1.0 185-195°
 
Derivative Type: Dihydrochloride
Molecular Formula: C15H24N2O.2HCl
Molecular Weight: 321.29
Percent Composition: C 56.07%, H 8.16%, N 8.72%, O 4.98%, Cl 22.07%
Properties: Deliquescent prisms, mp 185° (dec).
Melting point: mp 185° (dec)
 
Derivative Type: Hydrochloride dihydrate
Molecular Formula: C15H24N2O.HCl.2H2O
Molecular Weight: 320.86
Percent Composition: C 56.15%, H 9.11%, N 8.73%, O 14.96%, Cl 11.05%
Properties: Crystals, mp 177-178°. mp 250-252° (dry).
Melting point: mp 177-178°; mp 250-252° (dry)
 
Derivative Type: d-Form
CAS Registry Number: 550-90-3
Additional Names: 2-Oxosparteine
Properties: Syrup crystallizing difficultly in hygroscopic needles, mp 40-44°. bp3 190-193°. nD24 1.5444. [a]D25 +84° (c = 4.8 in alc). Freely sol in water, alcohol, chloroform, ether. Sol in petr ether.
Melting point: mp 40-44°
Boiling point: bp3 190-193°
Optical Rotation: [a]D25 +84° (c = 4.8 in alc)
Index of refraction: nD24 1.5444
 
Derivative Type: Hydrochloride dihydrate
Molecular Formula: C15H24N2O.HCl.2H2O
Molecular Weight: 320.86
Percent Composition: C 56.15%, H 9.11%, N 8.73%, O 14.96%, Cl 11.05%
Properties: Rhombic crystals from water, mp 127° (dry).
Melting point: mp 127° (dry)
 
Derivative Type: l-Form
CAS Registry Number: 486-88-4
Additional Names: Hydrorhombinine
Properties: Viscous oil, bp1.0 186-188°. [a]D about -61° in acetone.
Boiling point: bp1.0 186-188°
Optical Rotation: [a]D about -61° in acetone
 
Derivative Type: a-Isolupanine
CAS Registry Number: 486-87-3
Literature References: cis-cis-Isomer of lupanine: Marion, Leonard, Can. J. Chem. 29, 355 (1951). Isoln of d-form from Lupinus sericeus Pursh., L. perennis L. and L. augustifolius, Leguminosae: Marion et al., ibid. 31, 181 (1953); Rink, Schäfer, Arch. Pharm. 287, 290 (1954); Winterfeld, Pies, ibid. 290, 537 (1957).
Properties: Needles from petr ether, mp 75-76°. [a]D26 +39° (c = 0.77). [a]D26 +65.9° (c = 3.4 in abs ethanol).
Melting point: mp 75-76°
Optical Rotation: [a]D26 +39° (c = 0.77); [a]D26 +65.9° (c = 3.4 in abs ethanol)

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