CAS No 518-69-4 , (13S,13aR)-2,3,9,10-tetramethoxy-13-methyl-6,8,13,
13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

Title: Corydaline
CAS Registry Number: 518-69-4
CAS Name: (13S-trans)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-13-methyl-6H-dibenzo[a,g]quinolizine
Synonyms: 2,3,9,10-tetramethoxy-13a-methyl-13ab-berbine; d-corydaline
Molecular Formula: C22H27NO4
Molecular Weight: 369.45
Percent Composition: C 71.52%, H 7.37%, N 3.79%, O 17.32%
Literature References: Alkaloid isolated from many species of Corydalis. Discovery in C. tuberosa: Wackenroder, Kustner's Arch. 8, 423 (1826), as cited in: C. Wehmer, Die Pflanzenstoffe I (G. Fischer, Jena, 1929) p 389. Isoln from Corydalis aurea Willd. and C. solida (L.) Swartz, Fumariaceae: Manske, Can. J. Res. 16B, 81 (1938); Can. J. Chem. 34, 1 (1956). Structure: von Bruchhausen, Stippler, Arch. Pharm. 265, 152 (1927). Synthesis: Sp?th, Kruta, Ber. 62, 1024 (1929); T. Kametani et al., J. Chem. Soc. Perkin Trans. 1 1977, 1151; M. Cushman, F. W. Dekon, Tetrahedron 1978, 1435; Z. Kiparissides et al., Can. J. Chem. 58, 2770 (1980). Stereochemistry: Bersch, Arch. Pharm. 291, 595 (1958); Jeffs, Experientia 21, 690 (1965). Pharmacology: Berezhinskaya, C.A. 78, 119087j (1973). Toxicity study: R. C. Anderson, K. K. Chen, Fed. Proc. 5, 163 (1946).
Properties: Prisms from alc, mp 135°. [a]D20 +311° (c = 0.8 in alc). uv max: 396 nm. Sol in chloroform; moderately sol in ether; sparingly sol in methanol, ethanol. Practically insol in water. LD50 in mice (mg/kg): 135.5 ± 12.8 i.v. (Anderson, Chen).
Melting point: mp 135°
Optical Rotation: [a]D20 +311° (c = 0.8 in alc)
Absorption maximum: uv max: 396 nm
Toxicity data: LD50 in mice (mg/kg): 135.5 ± 12.8 i.v. (Anderson, Chen)
 
Derivative Type: Hydrochloride hydrate
Molecular Formula: C22H27NO4.HCl.H2O
Molecular Weight: 423.93
Percent Composition: C 62.33%, H 7.13%, N 3.30%, O 18.87%, Cl 8.36%
Properties: Four-sided columns, mp 230-240°.
Melting point: mp 230-240°
 
Derivative Type: dl-Form
Properties: mp 135°. Slightly sol in water.
Melting point: mp 135°
 
Derivative Type: dl-Mesocorydaline
Properties: mp 158°. The (13R-cis)-analog of corydaline. Slightly sol in water.
Melting point: mp 158°
 
Derivative Type: d-Mesocorydaline
Properties: Rhombic crystals, mp 152°. [a]D20 +82° (c = 1.4); +180° (c = 3 in chloroform).
Melting point: mp 152°
Optical Rotation: [a]D20 +82° (c = 1.4); +180° (c = 3 in chloroform)
 
Derivative Type: l-Mesocorydaline
Properties: Rhombic crystals, mp 152°. [a]D20 -85° (c = 1.4); -181° (c = 3 in chloroform).
Melting point: mp 152°
Optical Rotation: [a]D20 -85° (c = 1.4); -181° (c = 3 in chloroform)