Nabilone

(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one

Overview

Nabilone belongs to Cannabinoids.

Key safety note: Nabilone is fully psychoactive, and its commonest problems are central-nervous-system effects: dizziness/vertigo, drowsiness, dry mouth, ataxia, headache, disorientation, depersonalization and euphoria or dysphoria.[3]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology, mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or desirable outcomes.
  • Cannabis-like effects: relaxation, euphoria (or dysphoria/anxiety), altered perception of time and surroundings, and drowsiness, alongside relief of nausea.
  • Physical effects: dry mouth, dizziness, a faster heart rate, light-headedness on standing, unsteadiness and impaired coordination.
  • At higher doses or in susceptible people: confusion, disorientation, depersonalization and, uncommonly, hallucinations or panic.
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a “safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start low, go slow, wait for full effects before redosing, and never assume an unknown product matches these figures. Missing data is not evidence of safety.

Oral (capsules): prescription antiemetic, taken as a course around chemotherapy. Figures are therapeutic (prescribing) ranges, not a recreational guide.. Nabilone is a prescription medicine dosed by a clinician. It is fully psychoactive, so doses are kept low and titrated, and patients should not drive until they know how it affects them and should avoid alcohol and other sedatives. It is typically started the night before or a couple of hours before chemotherapy.

Dose ranges

Usual (adult)

1–2 mg twice daily

Maximum

6 mg/day (in divided doses)

Duration

onset

≈1–1.5 h (oral)

total

Effects last several hours, metabolite effects can persist longer

after effects

Drowsiness, dry mouth and light-headedness may linger

Chemical & Physical Properties
FormulaC24H36O3
Molar mass372.5 g/mol
StateSolid
Melting pointNot reported
Boiling pointNot reported
DensityNot reported
Vapor pressureNot reported
pKaNot reported
LogP6.8 (highly lipophilic)
SolubilityPractically insoluble in water (~4.9×10⁻⁴ g/L)
Refractive indexNot reported
Identifiers & Synonyms
CAS51022-71-0
CAS (enantiomer)
PubChem CID5284592
InChIKeyGECBBEABIDMGGL-RTBURBONSA-N
InChIInChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
SMILESCCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=O)CC[C@H]3C(OC2=C1)(C)C)O

Synonyms

  • Cesamet
  • Canemes
Pharmacodynamics & Biochemistry

Nabilone (Cesamet) is a synthetic cannabinoid: a close structural analogue of Δ⁹-THC (a ketone analogue of a THC metabolite) developed as a prescription antiemetic. Like THC it is an agonist at the CB1 and CB2 cannabinoid receptors, but it binds with higher affinity and greater efficacy: at human receptors its Kᵢ is about 4 nM (CB1) and 6 nM (CB2), roughly an order of magnitude tighter than THC, though it is still best described as a partial agonist. Its antiemetic action comes from CB1 activation in the brainstem and higher centres that control nausea and vomiting. The same central CB1 agonism produces its psychoactive, cannabis-like effects (relaxation, euphoria or dysphoria, altered perception) and its sedative, appetite- and mood-modulating actions. It is fully psychoactive, which limits dosing and is why it is used when standard antiemetics fail. Nabilone is administered as a racemate of its two trans enantiomers, (6aR,10aR)-(−) and (6aS,10aS)-(+), shown below. It is extensively metabolised in the liver by several cytochrome-P450 enzymes to a number of (incompletely characterised) metabolites. The parent has a short (~2 h) plasma half-life while its metabolites persist much longer (~35 h), and oral bioavailability is limited (~20%) by first-pass metabolism.

Biological targets

  • CB1
  • CB2

Binding & functional measurements

TargetMeasurementSpecies
CB1 receptorpKi 8.4Human
CB2 receptorpKi 8.2Human
Pharmacokinetics
BioavailabilityOral ≈20% (extensive first-pass metabolism)
TmaxNot reported
Half-lifeParent ≈2 h, identified metabolites ≈35 h
VdNot reported
Protein bindingHigh (~97%, similar to THC)
MetabolismHepatic, by multiple CYP450 enzymes, to several incompletely characterised metabolites
ExcretionMainly biliary/faecal, with some renal
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual health factors. Missing harms should never be interpreted as evidence of safety.

Not reported

Nabilone is fully psychoactive, and its commonest problems are central-nervous-system effects: dizziness/vertigo, drowsiness, dry mouth, ataxia, headache, disorientation, depersonalization and euphoria or dysphoria. At higher doses it can cause anxiety, confusion, and, uncommonly, hallucinations or a psychotic reaction, so it is avoided or used cautiously in people with a history of psychosis or serious psychiatric illness. It can cause a fast heart rate and orthostatic (standing) drops in blood pressure, so caution is needed in cardiovascular disease and in the elderly, who are more sensitive. Its sedation and impairment add to those of alcohol, benzodiazepines and other depressants, and patients should not drive until they know how it affects them. Tolerance and some dependence can develop with sustained use. Effects are long-lasting because of the persistent metabolites.[3]

Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status, prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
Interactions & Contraindications

Drug interactions

Alcohol, Benzodiazepines, Opioids Additive sedation and psychomotor impairment with alcohol and other CNS depressants (including sedating antihistamines).[3]
Cannabis Additive CNS and cardiovascular effects with other psychoactive or cannabinoid drugs.[3]
Anticholinergic drugs, Stimulants (amphetamines, cocaine) Additive dry mouth, tachycardia and blood-pressure effects with anticholinergics and sympathomimetics.[3]
Drugs cleared by shared CYP enzymes (e.g. CYP2C9, CYP3A4) Possible pharmacokinetic interactions with drugs affecting or affected by hepatic CYP metabolism.[3]

Contraindications

Personal or family history of psychosis, schizophrenia or bipolar disorder history of psychosis or serious psychiatric illness.[3]
Cardiovascular disease, hypertension or arrhythmia arrhythmia, hypertension or ischaemic heart disease.[3]
Kidney or liver impairment caution in the elderly and in hepatic impairment.[3]
Pregnancy or breastfeeding[3]
Known hypersensitivity to the drug cannabinoid hypersensitivity.[3]
Usage & Context
  • A prescription antiemetic: its FDA/EMA-approved use is for nausea and vomiting caused by cancer chemotherapy in patients who have not responded adequately to conventional antiemetics.
  • Used off-label for chronic and neuropathic pain, fibromyalgia, multiple-sclerosis spasticity, and to help appetite, anxiety or sleep: a synthetic alternative to herbal cannabis with a defined, standardised dose.
  • It is not a recreational-market drug in the way herbal cannabis is, but it is psychoactive and controlled.
Sources & Evidence

Further Information