Nabilone (CED0005874)

Record Information
Version1.0
Creation Date2016-05-25 18:20:43 UTC
Update Date2026-05-14 16:40:11 UTC
Accession NumberCHEM022117
Identification
Common NameNabilone
ClassSmall Molecule
Description
Nabilone is an organic compound with the formula C24H36O3 and an average molecular weight of 372.54 g/mol. Nabilone belongs to the naphthopyranones, a subclass of naphthopyrans within the organic compounds. This compound is found in or released from two recorded sources: antennas in electrical and electronic equipment, and antiemetics and antinauseants in healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure is oral. Regarding its biological activity, nabilone has two recorded protein targets, acting as a partial agonist of cannabinoid receptor 2 (CNR2) and targeting cannabinoid receptor 1 (CNR1).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CesametKegg
Nabilone, (6ar-trans)-isomerHMDB
Nabilone, (cis-(+-))-isomerHMDB
Nabilone, (6as-trans)-isomerHMDB
Nabilone, (trans-(+-))-isomerHMDB
Lilly brand OF nabiloneHMDB
Chemical FormulaC24H36O3
Average Molecular Mass372.541 g/mol
Monoisotopic Mass372.266 g/mol
CAS Registry Number51022-71-0
IUPAC Name(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
Traditional Namenabilone
SMILES[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC
InChI IdentifierInChI=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
InChI KeyGECBBEABIDMGGL-RTBURBONSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Cyclic ketone
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00049 g/LALOGPS
logP7.5ALOGPS
logP6.36ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.2 m³·mol⁻¹ChemAxon
Polarizability44.91 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a6s-4059000000-d86f1fa9d2fb7b5aeb43Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-9006500000-fa969e22f9069b4dae8cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0209000000-ae7db58f0d0bea9253a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-007k-5309000000-fa6f8bf6ae3a68b350a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9142000000-06e05031e6b790e0575aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-93527ef802493b35cbc6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0139000000-9dff2b635e80d9a8a438Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0671-4698000000-c6c6c7afb91f8c400cdeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-e7cb0fa6cccff516dcecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0009000000-d48b82525261ced239a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0039000000-fc9aceb1067cf8a70471Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1009000000-89d93a87d01729ab9bc8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008i-9216000000-0c92b93a021eea604013Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0536-9101000000-910f891074aa1437ef37Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
868.0Log mg/kg[490:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
249Antiemetics and antinauseantsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)6.15009
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)8.01847
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)8.79696
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)3.89246
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)7.62922
Transient receptor potential cation channel subfamily M member 8 structureClick to view 3D structureTransient receptor potential cation channel subfamily M member 8Q7Z2W7HumansPredicted (SEA)5.29375
G-protein coupled receptor 55 structureClick to view 3D structureG-protein coupled receptor 55Q9Y2T6HumansPredicted (SEA)10.0426
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)7.55137
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)36.7448
Glycine receptor subunit alpha-1 structureClick to view 3D structureGlycine receptor subunit alpha-1P23415HumansPredicted (SEA)0.700643
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)17.4382
Transient receptor potential cation channel subfamily V member 5 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 5Q9NQA5HumansPredicted (SEA)1.08989
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)880.397
Gamma-aminobutyric acid receptor subunit beta-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-2P47870HumansPredicted (SEA)2.95827
Click to view 3D structureN-arachidonyl glycine receptorQ14330HumansPredicted (SEA)26.858
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)1214.76
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)12.8451
Transient receptor potential cation channel subfamily V member 4 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 4Q9HBA0HumansPredicted (SEA)31.6068
Transient receptor potential cation channel subfamily V member 3 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8NET8HumansPredicted (SEA)3.65891
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansPredicted (SEA)46.476
Click to view 3D structureTransient receptor potential cation channel subfamily V member 4Q9ERZ8Rattus norvegicusPredicted (SEA)19.0731
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1795.9
Click to view 3D structureTransient receptor potential cation channel subfamily M member 8Q8R455Rattus norvegicusPredicted (SEA)22.8098
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)2878.55
3-oxoacyl-[acyl-carrier-protein] synthase 1 structureClick to view 3D structure3-oxoacyl-[acyl-carrier-protein] synthase 1P9WQD9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)10.5875
Concentrations
Not Available
External Links
DrugBank IDDB00486
HMDB IDHMDB0014629
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNabilone
Chemspider ID4447641
ChEBI ID189797
PubChem Compound ID5284592
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7.
2. Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9.
3. Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9.
4. Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S.