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
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03k9-0197000000-02f99ed4da3fcd7169f32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-0a4i-0009000000-863f2f390ccd9c8fe9cf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-0a4i-0239000000-0e4f7fd6cc72c6827f662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-0493000000-413d38916c00ef6234a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-004i-0290000000-23fb1fb13cc8ffbba6bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0279000000-3fd78de5823f4e0b4e482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0006-0900000000-606aa97e25113b8052282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-014i-0090000000-499c21708d1be862ce182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-014i-0090000000-392361b62c78f2977a9e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0002-0900000000-7088a45fb84da09fea832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0udl-0890000000-c7254416b3809c79f5ad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-0090000000-58f6b8627e7b186b785c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-00dl-0590000000-1e1e1032320e700d92952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-0090000000-bc7eaade0ce179bad0402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-03dj-0359000000-cc024dc534a3a9f9b62f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-03dj-0279000000-b3426208b22197d787ad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-03dj-1298000000-931100d6611f22917d352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-01vn-1292000000-998d4e1ea9b86bb2e35e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-01vp-2192000000-9babb635554716a06e4e2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0019000000-cc5908feb634826561a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4092000000-0d5f8eeb3c3657604c0b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9240000000-ad77015ae37c6f2204e72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-4cb0ebdfaca0cd6a22d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-88786e42ff7bce36b1972016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3490000000-e6ffa5b4dc0e798b395b2016-08-03View Spectrum
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
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified1.060 mg/g dry wt details
9 Lb HammerDetected and Quantified0.924 mg/g dry wt details
97 SageDetected and Quantified0.939 mg/g dry wt details
AdonisDetected and Quantified0.790 mg/g dry wt details
Alien DawgDetected and Quantified0.107 mg/g dry wt
    • David S. Wishart,...
 details
Alien Sour AppleDetected and Quantified0.940 mg/g dry wt details
Black BossDetected and Quantified1.320 mg/g dry wt details
Blue DreamDetected and Quantified1.260 mg/g dry wt details
Blue DreamDetected and Quantified1.350 mg/g dry wt details
Blue DreamDetected and Quantified1.570 mg/g dry wt details
Blue DreamDetected and Quantified1.780 mg/g dry wt details
Bob MarleyDetected and Quantified1.040 mg/g dry wt details
ChemdawgDetected and Quantified1.460 mg/g dry wt details
Chemdawg #4Detected and Quantified1.020 mg/g dry wt details
Chemdawg #4Detected and Quantified1.120 mg/g dry wt details
Cookies and CreamDetected and Quantified0.697 mg/g dry wt details
Cosmic LotusDetected and Quantified0.899 mg/g dry wt details
Dairy QueenDetected and Quantified0.794 mg/g dry wt details
FLODetected and Quantified0.836 mg/g dry wt details
GabriolaDetected and Quantified0.0994 mg/g dry wt
    • David S. Wishart,...
 details
Goji OGDetected and Quantified0.914 mg/g dry wt details
Golden SageDetected and Quantified0.786 mg/g dry wt details
Gorilla GlueDetected and Quantified2.100 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.990 mg/g dry wt details
Grape StomperDetected and Quantified0.812 mg/g dry wt details
Grape StomperDetected and Quantified0.989 mg/g dry wt details
Hash PlantDetected and Quantified1.160 mg/g dry wt details
Hash PlantDetected and Quantified1.760 mg/g dry wt details
HemlockDetected and Quantified0.952 mg/g dry wt details
Island HoneyDetected and Quantified0.0572 mg/g dry wt
    • David S. Wishart,...
 details
JabberwockyDetected and Quantified0.984 mg/g dry wt details
JabberwockyDetected and Quantified1.030 mg/g dry wt details
Kandy KushDetected and Quantified1.810 mg/g dry wt details
Kush PuppyDetected and Quantified0.861 mg/g dry wt details
La ChocoDetected and Quantified2.970 mg/g dry wt details
Lemon BalmDetected and Quantified1.550 mg/g dry wt details
Lemon GojiDetected and Quantified0.147 mg/g dry wt details
Lemon OGDetected and Quantified2.460 mg/g dry wt details
Lemon SherbetDetected and Quantified1.990 mg/g dry wt details
Lemon SkunkDetected and Quantified0.945 mg/g dry wt details
Liberty HazeDetected and Quantified1.120 mg/g dry wt details
LohanDetected and Quantified0.721 mg/g dry wt details
Lucky CharmsDetected and Quantified0.327 mg/g dry wt details
Maui HazeDetected and Quantified1.020 mg/g dry wt details
Moby DickDetected and Quantified2.710 mg/g dry wt details
Nightmare CookieDetected and Quantified1.340 mg/g dry wt details
Orange SkunkDetected and Quantified3.350 mg/g dry wt details
Pineapple SkunkDetected and Quantified0.412 mg/g dry wt details
Pipe DreamDetected and Quantified0.776 mg/g dry wt details
Platinum DelightDetected and Quantified0.112 mg/g dry wt details
Purple EclipseDetected and Quantified1.450 mg/g dry wt details
QuadraDetected and Quantified0.107 mg/g dry wt
    • David S. Wishart,...
 details
Rocket FuelDetected and Quantified0.776 mg/g dry wt details
Rollex OGDetected and Quantified0.252 mg/g dry wt details
Sensi StarDetected and Quantified0.0966 mg/g dry wt
    • David S. Wishart,...
 details
Skunk HazeDetected and Quantified0.999 mg/g dry wt details
Skywalker OGDetected and Quantified1.730 mg/g dry wt details
SpectrumDetected and Quantified0.511 mg/g dry wt details
Star KillerDetected and Quantified0.275 mg/g dry wt details
Strawberry FieldsDetected and Quantified1.000 mg/g dry wt details
Strawberry FieldsDetected and Quantified1.420 mg/g dry wt details
Sunset SherbetDetected and Quantified0.894 mg/g dry wt details
Sunset SherbetDetected and Quantified1.230 mg/g dry wt details
Tangerine DreamDetected and Quantified0.082 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0818 mg/g dry wt details
The SauceDetected and Quantified0.225 mg/g dry wt details
Venom OGDetected and Quantified1.070 mg/g dry wt details
White WidowDetected and Quantified1.240 mg/g dry wt details
Wonder WomanDetected and Quantified0.868 mg/g dry wt details
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 ]