Dihydromethysticin
Names
IUPAC name
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
CAS Number
3D model (JSmol )
ChEMBL
ChemSpider
MeSH
C107882
UNII
show
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3
Key: RSIWXFIBHXYNFM-UHFFFAOYSA-N
show
COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3
Properties
Chemical formula
C15 H16 O5
Molar mass
276.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is Y N ?)
Infobox references
Chemical compound
Dihydromethysticin is one of the six major kavalactones found in the kava plant.[1]
Pharmacology [ ]
Dihydromethysticin has marked activity on the induction of , as does the related chemical desmethoxyyangonin .[2]
Both dihydromethysticin and methysticin induce the hepatic enzyme CYP1A1 , which increases the amount of the very highly carcinogenic benzo[a ]pyrene-7,8-dihydrodiol-9,10-epoxide in the body (via the metabolism of benzo[a ]pyrene ) and may be responsible for some of the toxic effects associated with kava consumption.[citation needed ]
Metabolism of benzo[
a ]pyrene yielding the
carcinogenic benzo[
a ]pyren-7,8-dihydrodiol-9,10-epoxide.
In vitro , dihydromethysticin possesses analgesic , anticonvulsant , and anxiolytic effects.[3] It has been found to act as a GABAA receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B .[4] [5]
References [ ]
^ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF) . Fiji School of Medicine . Archived from the original (PDF) on 2009-03-20. Retrieved 2009-09-04 .
^ Ma, Yuzhong; Karuna Sachdeva; Jirong Liu1; Michael Ford; Dongfang Yang; Ikhlas Khan; Clinton Chichester; Bingfang Yan (November 2004). "Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23". Drug Metabolism and Disposition . 32 (11): 1317–1324. doi :10.1124/dmd.104.000786 . PMID 15282211 . S2CID 43840844 .
^ Walden J, von Wegerer J, Winter U, Berger M, Grunze H (May 1997). "Effects of kawain and dihydromethysticin on field potential changes in the hippocampus". Progress in Neuro-psychopharmacology and Biological Psychiatry . 21 (4): 697–706. doi :10.1016/s0278-5846(97)00042-0 . PMID 9194150 . S2CID 34014477 .
^ Sarris, Jerome; Laporte, Emma; Schweitzer, Isaac (2011). "Kava: A Comprehensive Review of Efficacy, Safety, and Psychopharmacology". Australian & New Zealand Journal of Psychiatry . 45 (1): 27–35. doi :10.3109/00048674.2010.522554 . PMID 21073405 . S2CID 42935399 .
^ Singh YN, Singh NN (2002). "Therapeutic potential of kava in the treatment of anxiety disorders". CNS Drugs . 16 (11): 731–43. doi :10.2165/00023210-200216110-00002 . PMID 12383029 . S2CID 34322458 .
show Kava
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See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
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See also: Receptor/signaling modulators
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