NUCIFERINE Chemical Properties

Melting point:

165.5°C

Boiling point:

437.06°C (rough estimate)

Density 

1.1156 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

2-8°C

solubility 

DMSO : 11.11 mg/mL (37.61 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)

pka

7.87±0.20(Predicted)

form 

powder

color 

white to beige

optical activity

[α]/D -145 to -165°, c = 0.5 in ethanol

LogP

2.357 (est)

Safety Information

Safety Statements 

24/25

RIDADR 

UN 1544PSN1 6.1 / PGIII

HS Code 

29389090

Toxicity

LD50 orl-rat: 280 mg/kg AIPTAK 197,261,72

NUCIFERINE Usage And Synthesis

Uses

The lotus leaf alkaloid has the effect of weight loss and lipid reduction, and can be used for content determination/identification/pharmacological experiments.

Description

Nuciferine is an aporphine alkaloid from Nelumbo lutea, the ba~e yields colourless crystals when crystallized from EtOH. It is laevorotatory, the following specific rotations having been recorded; [α] ²²_D- 157.5° and - 215°. The ultraviolet spectrum has three absorption maxima at 230, 272 and 310 mp. Two methoxyl groups and one methylimino group are present and the alkaloid may be characterized as the hydrochloride, m.p. 241°C (in vacuo) and the methiodide, m.p. 177-8°C. The optically inactive base has been synthesized and has m.p. 136-7°C, giving a hydrochloride in the form of small colourless prisms from H20, m.p. 258°C (dec.).

Uses

Nuciferin is an drug candidate for the treatment of obesity-related diseases. It is not well studied and its pharmacokinetics in vivo have not been fully investigated.

Safety Profile

Poison by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.

References

Gulland, Haworth., J. Chern. Soc., 590 (1928)
Yunusov, Konovalova, Orekhov., Bull. Soc. Chim. Fr., 70 (1940)
Arthur, Cheung., J. Chern. Soc., 2306 (1959)
Kupchan et al., Tetrahedron, 19, 227 (1963)

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