Hyperforin

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Hyperforin
IUPAC name	(1S,5S,7S,8R)-4-hydroxy-8-methyl-3,5,7 -tris(3-methylbut-2-enyl)-8-(4-methylpent- 3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1] non-3-ene-2,9-dione
Identifiers
CAS number	[11079-53-1]
SMILES	CCCC(=O)[C@]12C(=O)C(=C([C@](C1=O) (C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C) CC=C(C)C)O)CC=C(C)C
Properties
Molecular formula	C35H52O4
Molar mass	536.78 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Hyperforin is one of the principal constituents identified in St John's wort. Hyperforin is a prenylated phloroglucinol believed to be the main active constituent responsible for its antidepressant effects.^[1] Hyperforin has been shown to inhibit the uptake of 5-HT(serotonin), dopamine, noradrenaline, GABA and glutamate.^[2] Hyperforin is also thought to be responsible for the induction of the cytochrome P450 enzymes CYP3A4 and CYP2C9 by binding to the Pregnane X Receptor (PXR).

[edit] As ejaculatory control

Hyperforin and other serotonin agonists significantly reduces the pelvic floor contractions elicited by 8-OH-DPAT.^[3] Thus, pharmacological modulation of the ejaculatory threshold using serotonin reuptake inhibitors and hyperforin may offer patients an option of achieving improved ejaculatory control.

[edit] See also

• St John's Wort
• Serotonin
• 5-HTP
• Hypericum

[edit] References