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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014629
Secondary Accession Numbers
  • HMDB14629
Metabolite Identification
Common NameNabilone
DescriptionNabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesn't have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ('trans').
Structure
Data?1582753201
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 Weight372.5408
Monoisotopic Molecular Weight372.266445018
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
CAS Registry Number51022-71-0
SMILES
[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00049 g/LNot Available
LogP6.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.20631661259
DarkChem[M-H]-191.39631661259
DeepCCS[M-2H]-232.1330932474
DeepCCS[M+Na]+207.3730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nabilone[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC3473.9Standard polar33892256
Nabilone[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC2930.6Standard non polar33892256
Nabilone[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC2924.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nabilone,1TMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(=O)CC[C@H]1C(C)(C)O22678.4Semi standard non polar33892256
Nabilone,1TMS,isomer #2CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CC=C(O[Si](C)(C)C)C[C@@H]212689.9Semi standard non polar33892256
Nabilone,1TMS,isomer #3CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(O[Si](C)(C)C)=C[C@@H]212683.8Semi standard non polar33892256
Nabilone,2TMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O22715.9Semi standard non polar33892256
Nabilone,2TMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O22826.0Standard non polar33892256
Nabilone,2TMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C)=CC[C@H]1C(C)(C)O23100.8Standard polar33892256
Nabilone,2TMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O22739.3Semi standard non polar33892256
Nabilone,2TMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O22830.8Standard non polar33892256
Nabilone,2TMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C)CC[C@H]1C(C)(C)O23112.1Standard polar33892256
Nabilone,1TBDMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(=O)CC[C@H]1C(C)(C)O22891.6Semi standard non polar33892256
Nabilone,1TBDMS,isomer #2CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CC=C(O[Si](C)(C)C(C)(C)C)C[C@@H]212934.3Semi standard non polar33892256
Nabilone,1TBDMS,isomer #3CCCCCCC(C)(C)C1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(O[Si](C)(C)C(C)(C)C)=C[C@@H]212913.7Semi standard non polar33892256
Nabilone,2TBDMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O23177.5Semi standard non polar33892256
Nabilone,2TBDMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O23185.3Standard non polar33892256
Nabilone,2TBDMS,isomer #1CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1CC(O[Si](C)(C)C(C)(C)C)=CC[C@H]1C(C)(C)O23302.4Standard polar33892256
Nabilone,2TBDMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O23181.8Semi standard non polar33892256
Nabilone,2TBDMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O23202.4Standard non polar33892256
Nabilone,2TBDMS,isomer #2CCCCCCC(C)(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O23314.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6s-4059000000-d86f1fa9d2fb7b5aeb432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nabilone GC-MS (1 TMS) - 70eV, Positivesplash10-004i-9006500000-fa969e22f9069b4dae8c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nabilone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 10V, Positive-QTOFsplash10-00di-0209000000-ae7db58f0d0bea9253a72016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 20V, Positive-QTOFsplash10-007k-5309000000-fa6f8bf6ae3a68b350a92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 40V, Positive-QTOFsplash10-00kf-9142000000-06e05031e6b790e0575a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 10V, Negative-QTOFsplash10-00di-0009000000-93527ef802493b35cbc62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 20V, Negative-QTOFsplash10-00di-0139000000-9dff2b635e80d9a8a4382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 40V, Negative-QTOFsplash10-0671-4698000000-c6c6c7afb91f8c400cde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 10V, Negative-QTOFsplash10-00di-0009000000-e7cb0fa6cccff516dcec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 20V, Negative-QTOFsplash10-00di-0009000000-d48b82525261ced239a62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 40V, Negative-QTOFsplash10-014i-0039000000-fc9aceb1067cf8a704712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 10V, Positive-QTOFsplash10-00di-1009000000-89d93a87d01729ab9bc82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 20V, Positive-QTOFsplash10-008i-9216000000-0c92b93a021eea6040132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nabilone 40V, Positive-QTOFsplash10-0536-9101000000-910f891074aa1437ef372021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00486 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00486 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00486
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447641
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNabilone
METLIN IDNot Available
PubChem Compound5284592
PDB IDNot Available
ChEBI ID189797
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:375088 ]
  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. [PubMed:2838294 ]
  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. [PubMed:3039831 ]
  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. [PubMed:6271844 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:
CNR1
Uniprot ID:
P21554
Molecular weight:
52857.4
References
  1. Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. [PubMed:17139494 ]
  2. Darmani NA: The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2. Eur J Pharmacol. 2001 Oct 26;430(1):49-58. [PubMed:11698062 ]
  3. Hirst RA, Almond SL, Lambert DG: Characterisation of the rat cerebella CB1 receptor using SR141716A, a central cannabinoid receptor antagonist. Neurosci Lett. 1996 Dec 13;220(2):101-4. [PubMed:8981483 ]
  4. Pertwee RG: Cannabis and cannabinoids: pharmacology and rationale for clinical use. Forsch Komplementarmed. 1999 Oct;6 Suppl 3:12-5. [PubMed:10575283 ]
  5. Pertwee RG, Fernando SR: Evidence for the presence of cannabinoid CB1 receptors in mouse urinary bladder. Br J Pharmacol. 1996 Aug;118(8):2053-8. [PubMed:8864542 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]