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From the plant

CBDACannabidiolic acid

The native acid of CBD, produced by CBDA synthase; heat converts it into CBD.

Hemp exemption
Level of detail

C₂₂H₃₀O₄

CAS 1244-58-2

Family
PhytocannabinoidPrincipal
Origin
Biosynthesis (plant)
First described
1955
Molar mass
358.47 g/mol

Updated on

In plain terms

CBDA is the acid form of CBD that the living plant makes with an enzyme, CBDA synthase. When heated, it loses a carboxyl group and becomes CBD. Its effects in humans have not been studied on their own.

Receptors and activity

Target network

5-HT1AModulatorno measured value
  • Activates
  • Blocks or inhibits
  • Binds or modulates

The lower the cited value, the closer the target sits to CBDA: 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 CBDA.

Brain, side view
Body, front view
Blood

5-HT1A5-HT1A found in 6 regions of the body

  1. HippocampusdenseVery dense in the hippocampal CA1 field1
  2. BrainstemdenseHigh density in the raphe nuclei1
  3. CortexdenseDense in cortical layers I and II1
  4. AmygdaladenseHigh density in some amygdala nuclei1
  5. HypothalamuspresentIntermediate density, posterior hypothalamus1
  6. Spinal cordpresentPresent in the cervical spinal cord1

Map sources

  1. Pazos A et al. Serotonin receptors in the human brain--III. Autoradiographic mapping of serotonin-1 receptors. Neuroscience, 1987 (new tab)

Cited values

  1. COX-2InhibitorIC50 = 2 µM · not specified28 out of 100

    Takeda et al. 2008, Drug Metab Dispos (new tab) · enzymatic inhibition of COX-2; selectivity about 9 times higher vs COX-1

  2. 5-HT1AModulatorno measured value cited
  3. CB2Partial agonistKi = 12 nM · human65 out of 100

    Zagzoog et al. 2020, Sci Rep (new tab) · [3H]CP55940 displacement, CHO-hCB2 (IC95 4.9–77 nM); cAMP inhibition Emax 32% of CP55940; single study

  4. TRPA1AgonistEC50 = 5.3 µM · rat21 out of 100

    De Petrocellis et al. 2011, Br J Pharmacol (new tab) · intracellular Ca2+, HEK-293 expressing rat TRPA1; efficacy 113% of allyl isothiocyanate

  5. TRPM8AntagonistIC50 = 4.8 µM · rat22 out of 100

    De Petrocellis et al. 2011, Br J Pharmacol (new tab) · inhibition of the Ca2+ response to icilin, HEK-293 expressing rat TRPM8

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 CBDA, 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

CBDA is the main acid of fibre-type hemp: CBDA synthase, which forms it from CBGA, is the enzyme that determines this chemotype (Taura 2007). Purified in 1996 and cloned in 2007, this flavinylated oxidase needs neither molecular oxygen nor peroxide (Taura 1996). CBDA was first isolated in 1955 by Krejčí and Šantavý (Radwan 2021); heat decarboxylates it into CBD, and its decarboxylation kinetics have been measured in hemp seed oil (Citti 2018). In vitro, it inhibits COX-2 (IC50 ≈ 2 µM, about 9-fold more selective than for COX-1; Takeda 2008). In rat brainstem, it increased the maximal effect of the 5-HT1A agonist 8-OH-DPAT between 0.1 and 100 nM; in the same study, in rats and in the house musk shrew Suncus murinus, it reduced nausea-like behaviour and induced vomiting at lower doses than CBD, an effect blocked by the 5-HT1A antagonist WAY100635 (Bolognini 2013). One study reports a Ki of 12 nM at the human CB2 receptor, with partial agonism, against more than 10 µM at CB1 (Zagzoog 2020). In 15 healthy adults who took an oral extract combining CBD and CBDA in roughly equal parts, CBDA Cmax was 19 to 25 times higher than that of CBD, with a tmax up to 2 times earlier (Elder 2025).

Key sources.

Biosynthetic pathway

Produced by the plant: CBDA synthase, a flavinylated oxidase, converts CBGA into CBDA by oxidocyclisation; it also accepts cannabinerolic acid, with a lower kcat (0.03 versus 0.19 s-1) (Taura 1996; Taura 2007). Heat then decarboxylates CBDA into CBD.

Classification

Family, origin and source verification

Family

Phytocannabinoid › Principal

Presence in the plant

Enzymatic biosynthesis in the plant

Chemistry

Type CBD · C5 side chain · acid form

Verification

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

Wikipedia (English)

Cannabidiolic acid (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. Taura et al. 1996, J Biol Chem: purification of CBDA synthase (new tab)PMID 8663284
  2. Taura et al. 2007, FEBS Lett: cloning, fibre chemotype (new tab)PMID 17544411
  3. Takeda et al. 2008, Drug Metab Dispos: selective inhibition of COX-2 (new tab)PMID 18556441
  4. Bolognini et al. 2013, Br J Pharmacol: 5-HT1A, animal models of nausea (new tab)PMID 23121618
  5. Zagzoog et al. 2020, Sci Rep: human CB1/CB2 (new tab)PMID 33230154
  6. Elder et al. 2025, Cannabis Cannabinoid Res: human pharmacokinetics (new tab)PMID 40040421
  7. Citti et al. 2018, J Pharm Biomed Anal: decarboxylation kinetics (new tab)PMID 29182999

Identifiers

Names

Common name
Cannabidiolic acid
IUPAC name
2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
Other names
CBD-A

Identifiers

Formula
C₂₂H₃₀O₄
CAS
1244-58-2
PubChem CID
160570(new tab)
ChEBI
3359(new tab)
InChIKey
WVOLTBSCXRRQFR-DLBZAZTESA-N
SMILES
CCCCCC1=CC(=C(C(=C1C(=O)O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O

Machine-readable entry (JSON)

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

In the Journal