Naringenin is a flavonoid found in white grapefruit in large amounts and is partially responsible for its effects on enzymes.
Blocking Psychedelic Action of Allylbenzenes
Anecdotal reports indicate that pre-treatment with 20 mg naringenin or 2 cups of white grapefruit juice containing large amounts of naringenin can block or delay the onset of the psychedelic effects of allylbenzenes by 4-8 hours.
Naringenin is known to potently inhibit oxidative Estradiol 17beta-dehydrogenase Type 2.
Allylbenzenes require oxidation by Estradiol 17beta-dehydrogenase Type 2 before they can form 1'-oxo metabolites (such as 1'-oxoestragole from methyl chavicol). Many studies on PubMed indicate that only the 1'-oxo metabolites of allylbenzenes are able to form alkaloids.
See the articles Estradiol 17beta-dehydrogenase Type 2, Oilahuasca Activation, 1'-oxoestragole, and 1'-oxosafrole for more information.
Effects on Enzymes
Sulfotransferase | Interaction | Dosage | Verified in Man |
---|---|---|---|
SULT1A1 | Significant inhibition[2] | ? | ? |
SULT1A3 | Partial inhibition[2] | ? | ? |
Monoamine Oxidase | Interaction | Dosage | Verified in Man |
MAO-B | Moderate Inhibition | IC50=288 µM[1] | ? |
P-Glycoprotein | Interaction | Dosage | Verified in Man |
P-Ggp | Inhibition [3] | ? | ? |
Xanthine Oxidase | Interaction | Dosage | Verified in Man |
XO | Moderate Inhibition | IC50=50-100 μM[4] | ? |
17bHSD2 | Interaction | Dosage | Verified in Man |
Oxidative 17bHSD2 | 50% inhibition | IC50=14.4 µM[5] | ? |
Chemical Properties
PubChem Compound ID: 932
Molecular Weight: 272.25278 [g/mol]
Molecular Formula: C15H12O5
XLogP3-AA: 2.4
H-Bond Donor: 3
H-Bond Acceptor: 5
IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)
20-13/h1-6,13,16-18H,7H2
InChIKey: FTVWIRXFELQLPI-UHFFFAOYSA-N
Canonical SMILES : C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O