Showing Compound Card for Cannabinol (CDB000029)

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Record Information
Version1.0
Created at2020-03-19 00:36:27 UTC
Updated at2022-12-13 21:21:43 UTC
CannabisDB IDCDB000029
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabinol
DescriptionCannabinol (CBN), belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol is the best known and most abundant member of the cannabinoid subclass of cannabis compounds known as cannabinols or CBNs. Cannabinol is psychoactive, although in a lesser degree as THC and related compounds. CBN is most likely a degradation product of tetrahydrocannabinoic acid (THCA) or of tetrahydrocannabinol (THC). CBN can also be obtained through the decarboxilation of cannabinolic acid (CBNA), another product of the degradation of THCA (PMID: 1140243 ). Independently of the routes by which CBN is produced, it is found in higher quantities in Cannabis products that have been stored over an extended period of time or that have been exposed to sunlight or heat (PMID: 26870049 ). CBN is mildly psychoactive (PMID: 1221432 ) and acts as a partial agonist of the CB1 and CB2 receptors, with a higher affinity for the CB2 receptors (PMID: 11020293 ). In both cases the affinity of CBN to these receptors is lower than that of THC (PMID: 9667767 ). The legal status of CBN is uncertain, as it is not included in the United Nations’ Convention on Psychotropic Substances. However, it could still be considered as an analogue of THC in some states of the United States of America, leaving open the possibility of penal prosecution. The main pharmacological characteristics of Cannabinol are sedative, antibiotic, anticonvulsant and anti-inflammatory (PMID: 6991645 ). Cannabinol (CBN) is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-olPhytoBank
3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyranPhytoBank
CBNPhytoBank
Chemical FormulaC21H26O2
Average Molecular Weight310.44
Monoisotopic Molecular Weight310.1933
IUPAC Name6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol
Traditional Namecannabinol
CAS Registry Number521-35-7
SMILES
CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1
InChI Identifier
InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3
InChI KeyVBGLYOIFKLUMQG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentDibenzopyrans
Alternative Parents
Substituents
  • Dibenzopyran
  • 2-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.58ALOGPS
logP6.41ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.74 m³·mol⁻¹ChemAxon
Polarizability37.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ugm-5190000000-4449dbc8fa340a46930aSpectrum
Predicted GC-MSCannabinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabinol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Cannabinoid receptor 1CNR16q14-q15P21554 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
HMDB IDHMDB0249590
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002675
Chemspider ID2447
KEGG Compound IDC07580
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCannabinol
METLIN IDNot Available
PubChem Compound2543
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. [PubMed:1140243 ]
  3. Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. [PubMed:26870049 ]
  4. Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. [PubMed:1221432 ]
  5. Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK: Novel cannabinol probes for CB1 and CB2 cannabinoid receptors. J Med Chem. 2000 Oct 5;43(20):3778-85. doi: 10.1021/jm0001572. [PubMed:11020293 ]
  6. Petitet F, Jeantaud B, Reibaud M, Imperato A, Dubroeucq MC: Complex pharmacology of natural cannabinoids: evidence for partial agonist activity of delta9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors. Life Sci. 1998;63(1):PL1-6. doi: 10.1016/s0024-3205(98)00238-0. [PubMed:9667767 ]