Laureline
Title: Laureline
CAS Registry Number: 81-38-9
CAS Name: (7aR)-6,7,7a,8-Tetrahydro-11-methoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
Additional Names: 10-methoxy-1,2-(methylenedioxy)aporphine
Molecular Formula: C19H19NO3
Molecular Weight: 309.36
Percent Composition: C 73.77%, H 6.19%, N 4.53%, O 15.52%
Literature References: From bark of Laurelia novae-zelandiae A. Cunn., Lauraceae: Aston, J. Chem. Soc. 97, 1381 (1910). Synthesis: Schlittler, Helv. Chim. Acta 15, 394 (1932); Faltis et al., Ber. 77B, 686 (1945); Gibson et al., J. Chem. Soc. C 1970, 2234; Govindachari et al., Indian J. Chem. 8, 475 (1970).
Properties: Cubes from petr ether. [a]D20 -99.2° (c = 0.736 in 50% alc). Absorption spectrum: Girardet, J. Chem. Soc. 1931, 2636. Feebly basic. Readily oxidizes in air. Sol in alcohol, ether. Practically insol in water.
Optical Rotation: [a]D20 -99.2° (c = 0.736 in 50% alc)
 
Derivative Type: Hydrochloride
Molecular Formula: C19H19NO3.HCl
Molecular Weight: 345.82
Percent Composition: C 65.99%, H 5.83%, N 4.05%, O 13.88%, Cl 10.25%
Properties: Crystals, mp 280°. [a]D20 -57°. Sparingly sol in water.
Melting point: mp 280°
Optical Rotation: [a]D20 -57°
 
Derivative Type: (S)-Form
CAS Registry Number: 65981-49-9
Properties: Cubes from petr ether, mp 114-115°. [a]D20 +97.9° (c = 1.12 in abs alc); [a]D20 +100° (c = 0.560 in CS2).
Melting point: mp 114-115°
Optical Rotation: [a]D20 +97.9° (c = 1.12 in abs alc); [a]D20 +100° (c = 0.560 in CS2)
 
Derivative Type: (±)-Form
CAS Registry Number: 3749-97-1
Properties: Rough needles from petr ether, mp 115-116°.
Melting point: mp 115-116°
 
Derivative Type: Nitrate
Molecular Formula: C19H19NO3.HNO3
Molecular Weight: 372.37
Percent Composition: C 61.28%, H 5.41%, N 7.52%, O 25.78%
Properties: Crystals, mp 238-240°. Sparingly sol in water.
Melting point: mp 238-240°
 
Derivative Type: Hydriodide
Molecular Formula: C19H19NO3.HI
Molecular Weight: 437.27
Percent Composition: C 52.19%, H 4.61%, N 3.20%, O 10.98%, I 29.02%
Properties: Crystals. Practically insol in water.
 
Derivative Type: Oxalate
Molecular Formula: (C19H19NO3)2.(COOH)2
Molecular Weight: 708.75
Percent Composition: C 67.79%, H 5.69%, N 3.95%, O 22.57%
Properties: Moderately sol in water.

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