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From the plant

PETPerrottetinene

Bibenzyl analogue of THC formed by Radula liverworts, a partial CB1 agonist about ten times less potent than Δ9-THC.

FranceNarcotic: generic clauseInternationalUnscheduled
Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

C₂₄H₂₈O₂

CAS 160041-34-9

Family
PhytocannabinoidOutside cannabis
Origin
A plant other than hemp
Molar mass
348.48 g/mol

Updated on

In plain terms

Perrottetinene is a close chemical relative of THC, but it does not come from cannabis: it is made by small liverworts of the genus Radula. In mice, it acts on the same receptors as THC and produces effects of the same kind, at a higher dose. No study has been carried out in humans, and in France it has been classed as a narcotic under a generic clause since 2024.

Receptors and activity

Target network

CB1Partial agonistKi = 481 nM · human[3H]CP55,940 displacement, CHO-hCB1 membranes; partial agonism in [35S]GTPγS (EC50 406 nM)
  • Activates

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

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1Partial agonistKi = 481 nM · human39 out of 100

    Chicca et al. 2018, Sci Adv (new tab) · [3H]CP55,940 displacement, CHO-hCB1 membranes; partial agonism in [35S]GTPγS (EC50 406 nM)

  2. CB2Partial agonistKi = 225 nM · human44 out of 100

    Chicca et al. 2018, Sci Adv (new tab) · [3H]CP55,940 displacement, CHO-hCB2 membranes; partial agonism in [35S]GTPγS

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.

Pharmacology

Perrottetinene is a bibenzyl cannabinoid of liverworts of the genus Radula, absent from cannabis. It keeps the benzo[c]chromene skeleton of Δ9-THC, with a 2-phenylethyl chain in place of the pentyl chain and a cis ring junction where cannabis Δ9-THC is trans. Isolated in 1994 from Radula perrottetii, it received a pharmacology only in 2018: in mice, given intraperitoneally, the cis (50 mg/kg) and trans (40 mg/kg) forms produced the cannabinoid tetrad (hypothermia, catalepsy, hypolocomotion, analgesia) with a magnitude comparable to Δ9-THC at 10 mg/kg, and these effects were abolished by pretreatment blocking CB1 (Chicca 2018). At human CB1, the natural product has a Ki of 481 nM, against 22 nM for Δ9-THC in the same assay, and behaves as a partial agonist. Its brain-to-plasma concentration ratio was 0.91, against 0.51 for Δ9-THC. The authors describe it as the first psychoactive constituent known among more than 20,000 bryophyte species. No study exists in humans.

Key sources.

History

Source
Absent from cannabis: perrottetinene has never been reported in Cannabis sativa L. It is formed by liverworts of the genus Radula, bryophytes (non-vascular land plants) with no close relationship to hemp: Radula perrottetii in Japan, where it was isolated in 1994, then Radula marginata in New Zealand and Radula laxiramea (Chicca 2018). Like Δ9-THC, it is present in the plant as an acid, progressively decarboxylated on drying or smoking (Chicca 2018). Dried, wild-collected R. marginata is sold on the internet as a « legal high », with an uncertain perrottetinene content (Chicca 2018).

Biosynthetic pathway

Pathway not elucidated. In the plant, perrottetinene first exists as an acid, decarboxylated on drying or smoking (Chicca 2018), and candidate genes for its biosynthesis have been described in Radula marginata (Hussain et al. 2018, cited by Chicca 2018). Across 75 collections of R. marginata, chemotypes are dominated, depending on the site, by perrottetinene, by its CBD analogue (perrottetinene diol) or by its CBG analogue (bibenzyl-4-geranyl); they persist under artificial lighting and in in vitro culture, which suggests genetic control, and the authors see in this a convergent evolution of biosynthesis in two distant plant lineages (Andre 2025).

Classification

Family, origin and source verification

Family

Phytocannabinoid › Outside cannabis

Presence in the plant

Made by an organism other than cannabis

Chemistry

Bibenzyl (β-aralkyl) cannabinoid, THC-type skeleton with a cis ring junction · neutral form

Verification

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

Wikipedia (English)

Perrottetinene (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. Chicca A, Schafroth MA, Reynoso-Moreno I et al. 2018, Science Advances: Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high (new tab)PMID 30397641
  2. Andre CM, Sansom CE, Plunkett BJ et al. 2025, New Phytologist: Unique bibenzyl cannabinoids in the liverwort Radula marginata: parallels with Cannabis chemistry (new tab)PMID 39716766
  3. Song Y, Hwang S, Gong P et al. 2008, Organic Letters: stereoselective total synthesis of (−)-perrottetinene and assignment of its absolute configuration (new tab)PMID 18085788
  4. ANSM, decision of 22 May 2024 amending the list of substances classified as narcotics (generic benzo[c]chromene clause) (new tab)
  5. PubChem CID 24766094, perrottetinene (identifiers) (new tab)

Identifiers

Names

Common name
Perrottetinene
IUPAC name
(6aS,10aR)-6,6,9-trimethyl-3-(2-phenylethyl)-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Other names
cis-PET · Perrottetinen

Identifiers

Formula
C₂₄H₂₈O₂
CAS
160041-34-9
PubChem CID
24766094(new tab)
InChIKey
DYHMKBLKWFFFSZ-UXHICEINSA-N
SMILES
CC1=C[C@@H]2[C@H](CC1)C(OC3=C2C(=CC(=C3)CCC4=CC=CC=C4)O)(C)C

Machine-readable entry (JSON)

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