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biochanin ABiochanin A

A red clover isoflavone: a micromolar FAAH inhibitor, with no affinity for CB1 or CB2.

Unscheduled
Level of detail

C₁₆H₁₂O₅

CAS 491-80-5

Family
ECS pharmacological toolEnzyme inhibitor
Molar mass
284.26 g/mol

Updated on

In plain terms

Biochanin A is a molecule from red clover, a legume. It does not come from hemp and has no structural relationship with CBD. In the laboratory, it slows the enzyme that breaks down anandamide, a cannabinoid the body makes itself; in humans, the amounts measured in the blood after a red clover supplement remain well below the concentrations active in vitro.

Receptors and activity

Target network

FAAHInhibitorIC50 = 2.4 µM · humanhydrolysis of 0.5 µM AEA; IC50 of 1.4 µM (rat) and 1.8 µM (mouse); mixed inhibition, slope Ki 1.1 µM and intercept Ki 8.2 µM (rat FAAH)
  • Activates
  • Blocks or inhibits

The lower the cited value, the closer the target sits to biochanin A: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of biochanin A.

Brain, side view
Body, front view
Blood

FAAHFAAH found in 7 regions of the body

  1. CortexpresentCortical pyramidal neurons1
  2. Basal gangliapresentStriatal neurons1
  3. HypothalamuspresentPresent in hypothalamic nuclei1
  4. CerebellumpresentPurkinje cells and cerebellar layers1
  5. BrainstempresentInferior olivary nuclei1
  6. Adipose tissuepresentExpressed in mature adipocytes2
  7. BonepresentPresent on osteoclasts3

Map sources

  1. Romero J et al. Fatty acid amide hydrolase localization in the human central nervous system: an immunohistochemical study. Brain Res Mol Brain Res, 2002 (new tab)
  2. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  3. Rossi F et al. The endovanilloid/endocannabinoid system in human osteoclasts: possible involvement in bone formation and resorption. Bone, 2009 (new tab)

Cited values

  1. FAAHInhibitorIC50 = 2.4 µM · human27 out of 100

    Thors et al. 2010, Br J Pharmacol (new tab) · hydrolysis of 0.5 µM AEA; IC50 of 1.4 µM (rat) and 1.8 µM (mouse); mixed inhibition, slope Ki 1.1 µM and intercept Ki 8.2 µM (rat FAAH)

  2. URB597-sensitive cellular anandamide retentionInhibitorIC50 = 220 nM · rat44 out of 100

    Thors et al. 2010, Br J Pharmacol (new tab) · [3H]AEA retention, RBL2H3 cells

  3. PPARα and PPARγAgonistno measured value cited

    EC50 of 1 to 4 µM in reporter gene assays; PPARα/PPARγ ratio close to 1 to 1 with the full-length receptors (Shen 2006)

  4. Aromatase (CYP19)Inhibitorno measured value cited

    Inhibition of activity in MCF-7 cells expressing CYP19; fall in CYP19 mRNA at 25 µM in SK-BR-3 cells (Wang 2008)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Measured effects

Not characterised. No placebo-controlled human trial has measured the effects of biochanin A, so no level is shown.

Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method

Pharmacology

Described in 2010 as a natural FAAH inhibitor, biochanin A blocks anandamide hydrolysis with IC50 values of 1.4 µM (rat), 1.8 µM (mouse) and 2.4 µM (human enzyme), by mixed inhibition, with no effect on FAAH-2 and weak binding to the CB1 and CB2 receptors (Thors 2010). In mice, given intravenously (15 mg/kg), it did not raise brain anandamide but modestly potentiated its effects, and the authors conclude to FAAH inhibition in vitro and in the periphery. In 2022, Zada et al. measured an IC50 of 2.1 µM and, in mice treated for 14 days at 30 mg/kg, an increase in prefrontal cortex anandamide. Its effects cannot be attributed to the endocannabinoid system alone: it also activates PPARα and PPARγ (Shen 2006) and inhibits aromatase (Wang 2008). In humans, after 80 mg per day of a red clover extract, peak plasma concentrations of biochanin A and formononetin were about 48 ng/mL, i.e. 170 nM (Howes 2002, cited by Thors 2010), well below the IC50 values measured on FAAH. No clinical trial has assessed this endocannabinoid activity.

Key sources.

History

Source
A natural product of legumes, absent from cannabis. With formononetin, biochanin A is one of the predominant isoflavones of red clover (Trifolium pratense) (Roberts 2004), and it is found in the red clover extracts sold as food supplements (Wang 2008).

Origin

Research tool

The isoflavone pathway specific to legumes. The 4'-O-methylation that distinguishes biochanin A from genistein has not been characterised specifically for it; for formononetin, its analogue, the 4'-O-methyltransferases described act either at the 2-hydroxyisoflavanone intermediate stage or directly on the isoflavone, as in Pueraria lobata (Li 2016).

Classification

Family, origin and source verification

Family

ECS pharmacological tool › Enzyme inhibitor

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Biochanin A (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Thors et al. 2010, Br J Pharmacol: natural FAAH inhibitor (new tab)PMID 20590565
  2. Zada et al. 2022, Pharmacol Res Perspect: FAAH and isoflavonoids (new tab)PMID 36029006
  3. Shen et al. 2006, J Nutr: activation of PPARα and PPARγ (new tab)PMID 16549448
  4. Wang et al. 2008, Br J Nutr: aromatase inhibition (new tab)PMID 17761019
  5. Moon et al. 2006, AAPS J: pharmacokinetics in the rat (new tab)PMID 17025260
  6. Roberts et al. 2004, J Agric Food Chem: demethylation by CYP1A1 and CYP1B1 (new tab)PMID 15479032
  7. Howes et al. 2002, J Altern Complement Med: pharmacokinetics of a red clover extract (new tab)PMID 12006121
  8. Li et al. 2016, Front Plant Sci: 4'-O-methylation of isoflavones (new tab)PMID 27379141
  9. PubChem, Compound Summary CID 5280373 (biochanin A) (new tab)

Identifiers

Names

Common name
Biochanin A
IUPAC name
5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Other names
biochanine A · olmelin · pratensol

Identifiers

Formula
C₁₆H₁₂O₅
CAS
491-80-5
PubChem CID
5280373(new tab)
InChIKey
WUADCCWRTIWANL-UHFFFAOYSA-N
SMILES
COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.