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Valerenic acid

Valerenic acid


IUPAC name	(E)-3-[(4S,7R,7aR)-3,7-dimethyl- 2,4,5,6,7,7a-hexahydro- 1H-inden-4-yl]- 2-methylprop-2-enoic acid
Identifiers
CAS number	3569-10-6
PubChem	6440940
SMILES	CC1CCC(C2=C(CCC12)C)C=C(C)C(=O)O
Properties
Molecular formula	C₁₅H₂₂O₂
Molar mass	234.334
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Valerenic Acid is a constituent of the essential oil of the Valerian plant.

Additional recommended knowledge

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Valerian is used as a herbal sedative which may be helpful in the treatment of insomnia. While the precise mechanism of this action has not been established and it is likely that several different components of the plant contribute to the effect, valerenic acid is thought to be at least partly responsible for the sedative effects.

Valerenic acid has been demonstrated to be both a subtype-selective GABA_A agonist^[1] acting mainly at α1β2 and α1β3 subtypes,^[2] and also a 5HT_5A partial agonist.^[3] Both of these actions are likely to play a role in the sedative effects of this compound, as other GABA_A agonists such as benzodiazepines are commonly used as sedative drugs, and while no selective 5HT_5A agonists are currently used medically, the 5HT_5A receptor is known to be highly expressed in the suprachiasmatic nucleus of the brain, which is believed to be involved in the sleep-wake cycle.

Valerenic acid has also been reported to be an NF-κB inhibitor, and may be partly responsible for the reported anti-inflammatory action of the valerian plant.^[4]

References

^ Yuan CS, Mehendale S, Xiao Y, Aung HH, Xie JT, Ang-Lee MK. The gamma-aminobutyric acidergic effects of valerian and valerenic acid on rat brainstem neuronal activity. Anesthesia and Analgesia. 2004 Feb;98(2):353-8.
^ Khom S, Baburin I, Timin E, Hohaus A, Trauner G, Kopp B, Hering S. Valerenic acid potentiates and inhibits GABA(A) receptors: molecular mechanism and subunit specificity. Neuropharmacology. 2007 Jul;53(1):178-87.
^ Dietz BM, Mahady GB, Pauli GF, Farnsworth NR. Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro. Brain Research. Molecular Brain Research. 2005 Aug 18;138(2):191-7.
^ Jacobo-Herrera NJ, Vartiainen N, Bremner P, Gibbons S, Koistinaho J, Heinrich M. NF-kappaB modulators from Valeriana officinalis. Phytotherapy Research. 2006 Oct;20(10):917-9.