Cryogenine

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]

This article is about the alkaloid from the plants in the genus Heimia. For the antipyretic drug, see Phenicarbazide.
Cryogenine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (10α)-4,5-dimethoxy-2-hydroxylythran-12-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H29NO5
Molar mass435.520 g·mol−1
3D model (JSmol)
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
 NY (what is this?)  (verify)

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).

See also
  • List of entheogens

References
  1. Malone MH, Rother A (May 1994). "Heimia salicifolia: a phytochemical and phytopharmacologic review". Journal of Ethnopharmacology. 42 (3): 135–59. doi:10.1016/0378-8741(94)90080-9. PMID 7934084.
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