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Synthetic

Nabilone

A classical synthetic cannabinoid (dibenzopyran); antiemetic authorised by the FDA in 1985 (Cesamet).

FranceNarcotic: named in scheduleInternationalPrescription medicine
Level of detail

C₂₄H₃₆O₃

CAS 51022-71-0

Family
Synthetic CB receptor agonistResearch ligand or medicine
Origin
Synthetic (development code LY109514)
First described
1975
Molar mass
372.50 g/mol

Updated on

In plain terms

Nabilone is a laboratory-made cannabinoid, chemically close to THC, that activates the CB1 receptor. It is a prescription medicine, indicated for the nausea and vomiting of chemotherapy when the usual antiemetics are not enough. In France it is classified as a narcotic and has no marketing authorisation.

Receptors and activity

Target network

CB1AgonistKi = 5.1 nM · rat[3H]SR141716A displacement, rat cerebellar membranes (pKi 8.29 ± 0.08)
  • Activates

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

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. CB1AgonistKi = 5.1 nM · rat72 out of 100

    Hirst et al. 1996 · Neurosci Lett 220:101 (new tab) · [3H]SR141716A displacement, rat cerebellar membranes (pKi 8.29 ± 0.08)

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

Nabilone (LY109514) is a synthetic cannabinoid of the dibenzopyran class, studied in humans from 1975: single doses of 1 to 5 mg produced dose-dependent relaxant and sedative effects (Lemberger & Rowe 1975). The FDA approved it on 26 December 1985 (Cesamet, NDA 018677); the label indicates it for the nausea and vomiting of cancer chemotherapy in patients who have not responded to conventional antiemetics, and places it in Schedule II of the Controlled Substances Act. In the label's placebo-controlled trials (132 patients on nabilone, 119 on placebo), drowsiness and vertigo each affected 52% of patients, versus 5% and 3% on placebo, and euphoria 11% versus 1%. In 14 cannabis smokers, 4 to 8 mg increased ratings of « good effect », « strong effect » or « high » relative to placebo, with a later peak than dronabinol (Bedi et al. 2013). The active substance is the trans (±) racemate (GSRS). In Drugs@FDA, Cesamet was listed as « Discontinued » on 19/10/2026.

Key sources.

Approved medicines

Cesamet (nabilone)
Canemes (nabilone)

Origin

Laboratory synthesis

None: a fully synthetic cannabinoid of the dibenzopyran class (a 9-keto-hexahydrodibenzopyran with a 1,1-dimethylheptyl chain), described by the FDA label as chemically similar to Δ9-THC. The active substance is the trans (±) racemate. Described here by chemical class only.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › Research ligand or medicine

Class

classical

Verification

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

Wikipedia (English)

Nabilone (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. Lemberger & Rowe 1975 · Clin Pharmacol Ther 18:720 (new tab)PMID 1204278
  2. FDA · Cesamet label NDA 18-677/S-011 (2006) (new tab)
  3. Hirst et al. 1996 · Neurosci Lett 220:101 (new tab)PMID 8981483
  4. Bedi et al. 2013 · Addict Biol 18:872 (new tab)PMID 22260337
  5. EMA · list of national marketing authorisations for nabilone (EMA/328912/2024) (new tab)
  6. ANSM · consolidated list of narcotics (26/06/2026) (new tab)
  7. NCBI LiverTox: Nabilone (new tab)PMID 31643201

Identifiers

Names

IUPAC name
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
Other names
Cesamet · Canemes · LY109514 · CPD 109514

Identifiers

Formula
C₂₄H₃₆O₃
CAS
51022-71-0
PubChem CID
5284592(new tab)
ChEBI
CHEBI:135574(new tab)
InChIKey
GECBBEABIDMGGL-RTBURBONSA-N
SMILES
CCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=O)CC[C@H]3C(OC2=C1)(C)C)O

Machine-readable entry (JSON)

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