Hyperforin

Hyperforin
Clinical data
Dependence
liability
None
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • UK: General sales list (GSL, OTC)
  • US: OTC
  • unscheduled in most countries, with the notable exception of Ireland (Rx-only)
Pharmacokinetic data
MetabolismHepatic and CYP3A & CYP2B
Identifiers
  • (1R,5S,6R,7S)-4-Hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dion
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.112.565
Chemical and physical data
FormulaC35H52O4
Molar mass536.797 g·mol−1
3D model (JSmol)
Melting point79–80 °C (174–176 °F)
Solubility in water0.66 mg/mL (20 °C)
  • CC(C)C(=O)[C@@]21C(=O)[C@@](C[C@H](C\C=C(/C)C)[C@@]1(C)CC\C=C(/C)C)(C\C=C(/C)C)C(=O)C(\C\C=C(/C)C)=C2\O
  • InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1 Y
  • Key:IWBJJCOKGLUQIZ-HQKKAZOISA-N Y
 NY (what is this?)  (verify)

Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort). Hyperforin may be involved in the pharmacological effects of St. John's wort, specifically in its antidepressant effects. Meta-analyses of clinical trials suggest that H. perforatum is as effective as SSRIs for treating mild to moderate depression and is better tolerated, although findings are limited by short study durations.

Hyperforin is found in significant amounts only in H. perforatum, where it accumulates as a probable plant defense compound, with modern CO₂ extraction methods used to isolate it from mixtures containing related compounds like adhyperforin.