Cryogenine

This article is about the alkaloid from the plants in the genus Heimia. For the antipyretic drug, see Phenicarbazide.

Cryogenine
Systematic (IUPAC) name

(10α)-4,5-dimethoxy-2-hydroxylythran-12-one
Clinical data
Identifiers
CAS Registry Number	10308-13-1^N
ATC code	None
PubChem	CID 5315204
ChemSpider	4474587^N
ChEMBL	CHEMBL1173218^N
Chemical data
Formula	C₂₆H₂₉N O₅
Molecular mass	435.512 g/mol
SMILES O=C/4O[C@H]5C[C@@H]1N(CCCC1)[C@H](c2cc(OC)c(OC)cc2c3c(O)ccc(c3)\C=C\4)C5
InChI InChI=1S/C26H29NO5/c1-30-24-14-19-20(15-25(24)31-2)22-13-18(12-17-5-3-4-10-27(17)22)32-26(29)9-7-16-6-8-23(28)21(19)11-16/h6-9,11,14-15,17-18,22,28H,3-5,10,12-13H2,1-2H3/b9-7-/t17-,18+,22+/m1/s1 ^N Key:WCZWUYYJZVBKDZ-VMSBZHFZSA-N ^N
N (what is this?) (verify)

Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.^[1]

The freebase form melts at 250–251 °C and is soluble in moderately polar organic solvents such as chloroform, methylene chloride, benzene, and methanol, but is insoluble in water and petroleum ether.

In the development of thin layer chromatography plates with diazotized p-nitroaniline spray, cryogenine produces a purple spot (as does sinicuichine, another biphenylquinolizidine lactone alkaloid found in Heimia species).

References

↑ M. H. Malone, A. Rother (1994). "Heimia salicifolia: A phytochemical and phytopharmacologic review". J. Ethnopharmacol 42 (3): 135–159. doi:10.1016/0378-8741(94)90080-9. PMID 7934084.

Cryogenine

See also

References