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)[1]
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 Edit this at Wikidata
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 checkY
  • Key:IWBJJCOKGLUQIZ-HQKKAZOISA-N checkY
 ☒NcheckY (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).[2] Hyperforin may be involved in the pharmacological effects of St. John's wort,[2] specifically in its antidepressant effects.[3][4][5]

  1. ^ St John's Wort available again Archived 2020-08-02 at the Wayback Machine. Irishhealth.com (2015-10-13). Retrieved on 2020-02-11.
  2. ^ a b "Hyperforin". PubChem, US National Library of Medicine. 8 September 2018. Retrieved 13 September 2018.
  3. ^ Gaid M, Biedermann E, Füller J, Haas P, Behrends S, Krull R, et al. (May 2018). "Biotechnological production of hyperforin for pharmaceutical formulation". European Journal of Pharmaceutics and Biopharmaceutics. 126: 10–26. doi:10.1016/j.ejpb.2017.03.024. PMID 28377273. S2CID 4701643.
  4. ^ Ciochina R, Grossman RB (September 2006). "Polycyclic polyprenylated acylphloroglucinols". Chemical Reviews. 106 (9): 3963–3986. doi:10.1021/cr0500582. PMID 16967926.
  5. ^ Roz N, Rehavi M (October 2004). "Hyperforin depletes synaptic vesicles content and induces compartmental redistribution of nerve ending monoamines". Life Sciences. 75 (23): 2841–2850. doi:10.1016/j.lfs.2004.08.004. PMID 15464835.