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The 6 Main Kavalactones

Detailed effect profiles of the six most important active compounds in Piper methysticum.

Brief & Concise

Kavalactones (also called kava pyrones) are lipophilic constituents found in the genus Piper. Six major kavalactones make up most of the fraction normally measured in analysis and together shape kava's relaxing, anxiolytic, muscle-relaxing and mood-related effects.

Kavalactones (also called kava pyrones) are lipophilic constituents found in the genus Piper. Six major kavalactones make up most of the fraction normally measured in analysis and together shape kava's relaxing, anxiolytic, muscle-relaxing and mood-related effects.

To date, 18 different kavalactones have been identified in Piper methysticum, but six of them make up the majority of the total concentration and determine the effect profile of a Kava variety. These "Major Kavalactones" are coded with the numbers 1-6 and form the basis of the chemotype system.

Chemical Structure

All kavalactones share a common backbone: a α-pyron ring (a six-membered lactone ring) connected to a phenyl ring. The differences between the individual kavalactones arise from:

  • Methylenedioxy groups: Methysticin and Dihydromethysticin possess this group, which explains their longer duration of action.
  • Degree of saturation: The "Dihydro" variants (DHK, DHM) have a saturated side chain, which increases their lipophilicity and thus bioavailability.
  • Methoxy groups: Yangonin and Desmethoxyyangonin differ by the presence or absence of a methoxy group.
No.KavalactoneMolecular FormulaMolar MassFeature
1DesmethoxyyangoninC14H12O3228.24 g/molNo methoxy group
2DihydrokavainC14H16O3232.28 g/molSaturated side chain
3YangoninC15H14O4258.27 g/molWith methoxy group
4KavainC14H14O3230.26 g/molUnsaturated side chain
5DihydromethysticinC15H16O5276.29 g/molMethylenedioxy + saturated
6MethysticinC15H14O5274.27 g/molMethylenedioxy group

The 6 Main Kavalactones in Detail

Each of the six major kavalactones contributes a characteristic pharmacological profile. The chemotype is therefore a useful guide, while the experienced effect still depends on the whole profile, preparation, dose and individual response.

4

Kavain (K)

The "Lead Kavalactone" for Noble Kava

Kavain is strongly associated with the characteristic "heady" impression: clear, focused relaxation, a calmer mood and comparatively little physical heaviness. It appears near the front of many valued Noble profiles, although this digit alone does not establish quality.

Primary Effects

  • Anxiolytic
  • Mood-enhancing
  • Mental focus & clarity
  • Slight muscle relaxation

Mechanisms of Action

  • Modulation of GABA-A receptors
  • Blockade of voltage-gated Na⁺ channels
  • Inhibition of norepinephrine reuptake
  • Rapid blood-brain barrier passage
2

Dihydrokavain (DHK)

The "Body Relaxer"

Dihydrokavain is the hydrogenated form of kavain and makes a pronounced contribution to physical and muscular relaxation. Experimental work on sodium and calcium channels provides a plausible mechanism; in practice DHK is often described as calmer, more body-focused and gentler than kavain.

Primary Effects

  • Strong muscle relaxation
  • Analgesia
  • Physical relaxation
  • Sedating at high doses

Mechanisms of Action

  • Blockade of Ca²⁺ channels
  • Enhanced GABA-A modulation
  • Inhibition of glutamate release
  • Higher lipophilicity = better absorption
6

Methysticin (M)

The neuroprotective kavalactone

Methysticin is associated with marked physical calm, a heavier evening profile and sleep-supporting effects. Preclinical studies also investigate anxiolytic, anticonvulsant and neuroprotective mechanisms.

Primary Effects

  • Strongly sedating
  • Anxiolytic
  • Neuroprotective
  • Anticonvulsant

Research Interest

  • Protection against oxidative stress
  • Potential in Parkinson's research
  • Antiepileptic properties
  • Anti-inflammatory
5

Dihydromethysticin (DHM)

Deep, body-focused and longer-lasting calm

Dihydromethysticin is commonly associated with deep physical relaxation, sedation and a longer-lasting profile. A high relative level can contribute to a heavy character, while actual duration depends on the whole profile, dose and individual.

Properties

  • Tends to contribute to a longer-lasting profile
  • Strongly sedating
  • Can cause nausea
  • "Hangover" effect the next day

Occurrence

  • High in Tudei varieties (Isa, Palimanu)
  • High in Piper wichmannii (Wild Kava)
  • Low in Noble Kava
  • Marker for quality control
3

Yangonin (Y)

The endocannabinoid-active kavalactone

Yangonin shows in-vitro affinity for the CB1 receptor of the endocannabinoid system. This finding fits the mildly euphoric and mood-lifting side of some kava profiles, but it does not mean that yangonin acts like THC or that kava acts like cannabis.

Primary Effects

  • Slightly euphoric
  • Mood-enhancing
  • Appetite-modulating
  • Stimulating at low doses

Mechanisms of Action

  • Binding to CB1 receptors
  • MAO-B inhibition
  • Dopaminergic activity
  • Synergy with other kavalactones
1

Desmethoxyyangonin (DMY)

Focus, motivation and social openness

Desmethoxyyangonin differs from yangonin by the absence of a methoxy group. It is associated with the focused, motivating and socially open side of kava; possible monoaminergic and MAO-related mechanisms remain active areas of research.

Primary Effects

  • Focus & concentration
  • Mood-related monoaminergic modulation
  • Slight euphoria
  • Motivation enhancement

Mechanisms of Action

  • Inhibition of dopamine reuptake
  • MAO-B inhibition
  • Norepinephrine activity
  • Rapid onset of action

Mechanisms of Action of Kavalactones

Kavalactones affect the central nervous system on multiple levels simultaneously. This multimodality explains why the Kava effect is so unique and differs from other anxiolytics:

Mechanism of ActionInvolved KavalactonesResulting Effect
GABA-A modulationKavain, DHK, M, DHMAnxiolytic, relaxing, sedating
Na⁺ channel blockadeKavain, DHKAnalgesic, local anesthetic
Ca²⁺ channel blockadeDHK, DHMMuscle relaxing
MAO-B inhibitionY, DMYMood- and focus-related; investigated experimentally
In-vitro CB1 affinityYangoninMood-related component; not equivalent to THC
Norepinephrine reuptake inhibitionKavain, DMYFocusing, alertness-promoting

How the Kavalactones Work Together

Traditional kava contains several kavalactones and other plant constituents. Their interaction shapes the typical range of clear mental calm, mood lift and physical relaxation, although a fixed human entourage effect has not been conclusively established.

Kavain is especially associated with clear, anxiety-relieving relaxation, while Yangonin and Desmethoxyyangonin are more often linked to mood and focus. The precise contribution of each compound cannot yet be expressed as a clinical percentage.

Traditional water preparations made from the root can therefore produce a different overall profile from isolated compounds. The whole plant profile, root quality, preparation, dose and individual response all matter.

Practical Consequence

When purchasing Kava products, attention should be paid to full-spectrum extracts or traditionally prepared Kava. Products with isolated Kavain or standardized single active ingredients often do not provide the same effect profile as the natural root.

Continue in the chapter Ingredients:

The Chemotype System

How the six-digit code shows relative rank

Based on studies by

Vincent Lebot

CIRAD, French Agricultural Research Centre for International Development

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This wiki is a curated resource that synthesizes research from peer-reviewed studies and expert researchers. It is not written by the researchers listed above, but rather based on their published work.

Scientific Sources

The information on this page is based on the following scientific studies and publications:

Measuring the Chemical and Cytotoxic Variability of Commercially Available Kava (Piper methysticum G. Forster)

Unknown (Unknown) – Unknown

View study

In Vitro Toxicity of Kava Alkaloid, Pipermethystine, in HepG2 Cells Compared to Kavalactones

Nerurkar P.V., Dragull K., Tang C.S. (2004) – Toxicological Sciences

View study

Genetic control of kavalactone chemotypes in Piper methysticum cultivars

Lebot V., Levesque J. (1996) – Phytochemistry

View study
Last updated: March 18, 2026New study added