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Cryogenine information


Cryogenine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (10α)-4,5-dimethoxy-2-hydroxylythran-12-one
CAS Number
  • 10308-13-1 checkY
PubChem CID
  • 5315204
ChemSpider
  • 4474587 ☒N
UNII
  • OR77C8W8TA
ChEMBL
  • ChEMBL1173218 ☒N
CompTox Dashboard (EPA)
  • DTXSID201099973 Edit this at Wikidata
Chemical and physical data
FormulaC26H29NO5
Molar mass435.520 g·mol−1
3D model (JSmol)
  • Interactive image
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
 ☒NcheckY (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).

  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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Cryogenine

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Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi...

Word Count : 142

Heimia salicifolia

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Central America and Mexico.[citation needed] Source: Vertine, also known as cryogenine, is regarded as the primary bioactive component and is also generally...

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List of psychoactive plants

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flavum Hallucinogenic effects. Possibly Cryogenine[citation needed] Heimia myrtifolia Auditory Possibly Cryogenine[citation needed] Heimia salicifolia...

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Aztec use of entheogens

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ritualistic context. Multiple alkaloids have been isolated from the plant; with cryogenine, lythrine, and nesodine being the most important. Sinicuichi could be...

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List of psychedelic drugs

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stimulants Myristicin† and elemicin†, the active constituents of nutmeg Cryogenine (Vertine)†, the active constituent of certain Heimia species Atropine†...

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Heimia

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oxyphenyl)-quinolizidin-2-acetate Lythrine Dehydrodecodine Lythridine Cryogenine Heimidine Lyfoline epi-Lyfoline Sinicuichine Nesodine Abresoline Anelisine...

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