Hypericin
The red pigment of St. John's Wort, a weak MAO inhibitor and strong light-activated photosensitizer.
Pharmacology
Contents
WHAT IS HYPERICIN?
Detailed overview
Hypericin is a naphthodianthrone red pigment and one of the marker constituents of St. John's Wort (Hypericum perforatum), long associated with the plant's mood-supporting reputation. In preclinical studies it weakly inhibits monoamine oxidase and modestly influences serotonergic signaling, though the antidepressant effect of St. John's Wort is now attributed more to hyperforin than to hypericin. Its most pronounced pharmacological property is photodynamic: when it absorbs visible or ultraviolet light it is raised to an excited state and transfers that energy to surrounding oxygen, generating singlet oxygen and other reactive oxygen species, which underlies both its phototoxicity and its activity against enveloped viruses. Evidence for the isolated pigment is limited and mostly preclinical; human data almost always concern the standardized whole extract.
Mechanism
Weak MAO inhibition + light-activated ROS generation
Evidence
Limited (mostly preclinical)
Source
Pigment of St. John's Wort (Hypericum perforatum)
Receptor profile
- Reactive oxygen species (light-activated)Strong
- Enveloped virusesModerate
- Monoamine oxidaseWeak
- Serotonergic signalingWeak
Safety
Side effects, stop signs, contraindications
Side effects · 5
- Photosensitivity (phototoxicity): exaggerated sunburn and skin reactions in sunlight at higher intakes
- Skin rash, tingling or stinging on sun-exposed skin
- Eye sensitivity to bright light
- Mild stomach upset, nausea
- As part of St. John's Wort (Hypericum perforatum) extract, numerous drug interactions
Contraindications · 4
- Pregnancy and breastfeeding: safety not established, avoid
- Intense sun exposure or tanning beds: avoid at high doses due to phototoxic effect
- SSRIs, MAO inhibitors or other serotonergic agents: theoretical risk of serotonin syndrome
- As St. John's Wort extract, a strong CYP3A4 and P-glycoprotein inducer: may reduce the effect of contraceptives, anticoagulants, immunosuppressants and HIV drugs
Related Nootropics
Same therapeutic category
Studies
Related research and clinical findings
LC-MS/MS based studies on the anti-depressant effect of hypericin in the chronic unpredictable mild stress rat model
Zhai XJ, et al.
Long-term effects of St. John's wort and hypericin on monoamine levels in rat hypothalamus and hippocampus
Butterweck V, et al.
In vitro binding studies with two hypericum perforatum extracts--hyperforin, hypericin and biapigenin--on 5-HT6, 5-HT7, GABA(A)/benzodiazepine, sigma, NPY-Y1/Y2 receptors and dopamine transporters
Gobbi M, et al.
Inhibition of MAO and COMT by hypericum extracts and hypericin
Thiede HM, Walper A
Inhibition of monoamine oxidase by hypericin
Suzuki O, et al.
FAQ
FAQ
The red pigment of St. John's Wort, a weak MAO inhibitor and strong light-activated photosensitizer.
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Structure & chemistry
The information here is strictly for educational and scientific purposes. It does not replace medical advice or clinical consultation, and it does not encourage illegal substance or pharmaceutical use. Data is sourced. When in doubt, consult your doctor.