Narciclasine

June 04, 2018
I’m a potential cancer drug produced in flowers.
What molecule am I?

Narciclasine, also known as lycoricidinol, is an isocarbostyril alkaloid found in the Amaryllidaceae (amaryllis) family of flowering plants. One notable genus of the family is Narcissus, from which narciclasine gets its name. Daffodils and jonquils are members of the Narcissus genus.

In 1967, Giovanni Ceriotti, Luigi Spandrio, and Annivale Gazzaniga at Circolo Hospital (Busto Arsizio, Italy) isolated narciclasine from Narcissus varieties. At that time, it was known to inhibit cell division. By the early 2010s, narciclasine was an established antitumor agent.

In 2016, Robert Fürst at Goethe University (Frankfurt am Main, Germany) reviewed the antitumor and anti-inflammatory findings on narciclasine. At present, no clinical trials on narciclasine have been conducted on humans.

Narciclasine is sparingly soluble in water. But in 2003, George R. Petit and colleagues at Arizona State University (Tempe) synthesized a cyclic phosphate at two of the adjacent hydroxyl groups of narciclasine. The product, which they called narcistatin (CAS Reg. no. 496963-44-1), is much more water-soluble (4 g/L), making it a valuable prodrug for narciclasine.

Narciclasine fast facts

CAS Reg. No. 29477-83-6
Molar mass 307.26 g/mol
Empirical formula C14H13NO7
Appearance White to off-white powder
Melting point 246 ºC
Water solubility Slight

Narciclasine hazard information

GHS classification*: germ cell mutagenicity, category 1B
H340—May cause genetic defects  Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

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