Record Information
Version1.0
Created at2020-03-19 00:35:02 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000007
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabichromene
DescriptionCannabichromene, also known as CBC, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabichromene is a neutral compound. Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is one of the hundreds of cannabinoids found in the cannabis plant and is therefore a phytocannabinoid. It bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC is a product of the decarboxylation of cannabichromenic acid (CBCA), which occurs over time or after reaching temperatures above 90 °C. CBCA is a product of the cyclization of the main cannabinoid precursor, cannabigerolic acid (CBGA). CBC and its derivatives are as abundant as cannabinols in cannabis. CBC is not scheduled by the Convention on Psychotropic Substances. CBC has shown interesting anti-inflammatory activities in pre-clinical trials (PMID: 20619971 ). CBC is non-psychoactive and does not affect the psychoactivity of THC (PMID: 16148455 ). CBC acts on the transient receptor potential cation channel subfamily V member 1 (TRPV1) and transient receptor potential ankyrin 1 (TRPA1) receptors, interfering with their ability to break down endocannabinoids (the bodies endogenous cannabinoids, such as anandamide and 2-arachidonoylglycerol, 2-AG, the endogenous agonist for the cannabinoid-1 receptor, CB1 and primary ligand for cannabinoid-2 receptor, CB2).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H30O2
Average Molecular Weight314.47
Monoisotopic Molecular Weight314.2246
IUPAC Name(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol
Traditional Name(2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentylchromen-5-ol
CAS Registry Number20675-51-8
SMILES
CCCCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1
InChI Identifier
InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3/t21-/m0/s1
InChI KeyUVOLYTDXHDXWJU-NRFANRHFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.04ALOGPS
logP6.6ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.6 m³·mol⁻¹ChemAxon
Polarizability38.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabichromene, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Transient receptor potential cation channel subfamily V member 1TRPV117p13.2Q8NER1 details
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Transient receptor potential cation channel subfamily V member 1TRPV117p13.2Q8NER1 details
Cannabinoid receptor 1CNR16q14-q15P21554 details
Transient receptor potential cation channel subfamily A member 1TRPA18q13O75762 details
Cannabinoid receptor 2CNR21p36.11P34972 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified2.860 mg/g dry wt details
9 Lb HammerDetected and Quantified2.230 mg/g dry wt details
97 SageDetected and Quantified2.810 mg/g dry wt details
AdonisDetected and Quantified3.100 mg/g dry wt details
Alien BluesDetected and Quantified3.3 +/- 0.9 mg/g dry wt details
Alien DawgDetected and Quantified0.0539 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Sour AppleDetected and Quantified2.330 mg/g dry wt details
Black BossDetected and Quantified2.610 mg/g dry wt details
Blue Cherry PieDetected and Quantified1.4 +/- 0.7 mg/g dry wt details
Blue DreamDetected and Quantified2.650 mg/g dry wt details
Blue DreamDetected and Quantified1.3 +/- 0.1 mg/g dry wt details
Blue DreamDetected and Quantified2.780 mg/g dry wt details
Blue DreamDetected and Quantified3.980 mg/g dry wt details
Blue DreamDetected and Quantified4.240 mg/g dry wt details
Bob MarleyDetected and Quantified2.850 mg/g dry wt details
Bohdi TreeDetected and Quantified0.5 +/- 0 mg/g dry wt details
ChemdawgDetected and Quantified3.500 mg/g dry wt details
Chemdawg #4Detected and Quantified2.860 mg/g dry wt details
Chemdawg #4Detected and Quantified3.380 mg/g dry wt details
Cold Creek KushDetected and Quantified1.4 +/- 0 mg/g dry wt details
Cookies and CreamDetected and Quantified10.200 mg/g dry wt details
Cosmic LotusDetected and Quantified2.030 mg/g dry wt details
Crystal CookiesDetected and Quantified5.1 +/- 0.7 mg/g dry wt details
Dairy QueenDetected and Quantified2.710 mg/g dry wt details
Dark Shadow HazeDetected and Quantified3.130 mg/g dry wt details
Double Royal KushDetected and Quantified2.7 +/- 0.2 mg/g dry wt details
FLODetected and Quantified2.1 +/- 0.2 mg/g dry wt details
FLODetected and Quantified2.570 mg/g dry wt details
GabriolaDetected and Quantified0.0671 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Goji OGDetected and Quantified2.840 mg/g dry wt details
Golden CobraDetected and Quantified1.260 mg/g dry wt details
Golden SageDetected and Quantified2.600 mg/g dry wt details
Gorilla GlueDetected and Quantified2.800 mg/g dry wt details
Gorilla Glue #4Detected and Quantified2.510 mg/g dry wt details
Grandaddy PurpleDetected and Quantified2.2 +/- 0.1 mg/g dry wt details
Grape StomperDetected and Quantified2.320 mg/g dry wt details
Grape StomperDetected and Quantified2.330 mg/g dry wt details
Green CrackDetected and Quantified4.4 +/- 0.5 mg/g dry wt details
Green Crack 2015Detected and Quantified2 +/- 0.3 mg/g dry wt details
Grizzly KushDetected and Quantified1.880 mg/g dry wt details
Hash PlantDetected and Quantified4.980 mg/g dry wt details
Hash PlantDetected and Quantified2.420 mg/g dry wt details
HemlockDetected and Quantified2.300 mg/g dry wt details
Holy PowerDetected and Quantified3.4 +/- 0.2 mg/g dry wt details
Island HoneyDetected and Quantified0.0373 mg/g dry wt
    • Jiamin Zheng, Yil...
details
JabberwockyDetected and Quantified4.700 mg/g dry wt details
JabberwockyDetected and Quantified6.690 mg/g dry wt details
Jack HererDetected and Quantified2.810 mg/g dry wt details
JuanitaDetected and Quantified2.1 +/- 0 mg/g dry wt details
Kandy KushDetected and Quantified2.770 mg/g dry wt details
Kush PuppyDetected and Quantified2.120 mg/g dry wt details
La ChocoDetected and Quantified4.830 mg/g dry wt details
LavendarDetected and Quantified1.5 +/- 0.2 mg/g dry wt details
LavendarDetected and Quantified5 +/- 0.2 mg/g dry wt details
Lavendar Jones 2015Detected and Quantified3.2 +/- 0.5 mg/g dry wt details
Lemon BalmDetected and Quantified3.820 mg/g dry wt details
Lemon GojiDetected and Quantified4.530 mg/g dry wt details
Lemon OGDetected and Quantified3.950 mg/g dry wt details
Lemon SherbetDetected and Quantified6.440 mg/g dry wt details
Lemon SkunkDetected and Quantified3.580 mg/g dry wt details
Lemon SkunkDetected and Quantified4.040 mg/g dry wt details
Liberty HazeDetected and Quantified2.560 mg/g dry wt details
LohanDetected and Quantified1.330 mg/g dry wt details
Love LaceDetected and Quantified5.6 +/- 0.4 mg/g dry wt details
Lucky CharmsDetected and Quantified4.220 mg/g dry wt details
Maui HazeDetected and Quantified2.790 mg/g dry wt details
Moby DickDetected and Quantified2.730 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified2.030 mg/g dry wt details
Nightmare CookieDetected and Quantified2.810 mg/g dry wt details
OracleDetected and Quantified2.5 +/- 0.1 mg/g dry wt details
Orange SkunkDetected and Quantified7.050 mg/g dry wt details
Pineapple SkunkDetected and Quantified3.490 mg/g dry wt details
Pipe DreamDetected and Quantified2.610 mg/g dry wt details
Platinum BuffaloDetected and Quantified3.3 +/- 0.2 mg/g dry wt details
Platinum DelightDetected and Quantified2.420 mg/g dry wt details
Platinum GorillaDetected and Quantified3.7 +/- 0.2 mg/g dry wt details
Platinum ScoutDetected and Quantified3.4 +/- 0.2 mg/g dry wt details
Purple EclipseDetected and Quantified2.460 mg/g dry wt details
Purple Fat PieDetected and Quantified2.7 +/- 0.2 mg/g dry wt details
QuadraDetected and Quantified0.106 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Rocket FuelDetected and Quantified2.970 mg/g dry wt details
Rollex OGDetected and Quantified4.910 mg/g dry wt details
RomulinDetected and Quantified1.7 +/- 0.1 mg/g dry wt details
Rosetta StoneDetected and Quantified1.970 mg/g dry wt details
RXDetected and Quantified1.6 +/- 0.1 mg/g dry wt details
SatoriDetected and Quantified1.740 mg/g dry wt details
Sensi StarDetected and Quantified0.115 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Skunk HazeDetected and Quantified1.190 mg/g dry wt details
SkywalkerDetected and Quantified1.4 +/- 0 mg/g dry wt details
Skywalker OGDetected and Quantified4.720 mg/g dry wt details
Sour WillieDetected and Quantified1.4 +/- 0.4 mg/g dry wt details
SpectrumDetected and Quantified4.560 mg/g dry wt details
Star BudDetected and Quantified2.720 mg/g dry wt details
Star KillerDetected and Quantified1.420 mg/g dry wt details
Strawberry FieldsDetected and Quantified8.230 mg/g dry wt details
Strawberry FieldsDetected and Quantified8.570 mg/g dry wt details
Sunset SherbetDetected and Quantified5.030 mg/g dry wt details
Sunset SherbetDetected and Quantified5.420 mg/g dry wt details
Tangerine DreamDetected and Quantified0.0395 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified4.080 mg/g dry wt details
Tangerine DreamDetected and Quantified0.0357 mg/g dry wt
    • Jiamin Zheng, Yil...
details
The SauceDetected and Quantified1.500 mg/g dry wt details
ThunderstruckDetected and Quantified6.2 +/- 0.6 mg/g dry wt details
Twisted VelvetDetected and Quantified3.5 +/- 0.3 mg/g dry wt details
Venom OGDetected and Quantified4.780 mg/g dry wt details
Walker KushDetected and Quantified2.8 +/- 0.1 mg/g dry wt details
White WidowDetected and Quantified1.7 +/- 0.3 mg/g dry wt details
White WidowDetected and Quantified0.451 mg/g dry wt details
Wonder WomanDetected and Quantified2.200 mg/g dry wt details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21668219
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. DeLong GT, Wolf CE, Poklis A, Lichtman AH: Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Delta(9)-tetrahydrocannabinol. Drug Alcohol Depend. 2010 Nov 1;112(1-2):126-33. doi: 10.1016/j.drugalcdep.2010.05.019. [PubMed:20619971 ]
  2. Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H: Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids. Behav Pharmacol. 2005 Sep;16(5-6):487-96. doi: 10.1097/00008877-200509000-00023. [PubMed:16148455 ]

Transporters

General function:
Involved in ion channel activity
Specific function:
Receptor-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular acidosis in nociceptive neurons. May be involved in mediation of inflammatory pain and hyperalgesia. Sensitized by a phosphatidylinositol second messenger system activated by receptor tyrosine kinases, which involves PKC isozymes and PCL
Gene Name:
TRPV1
Uniprot ID:
Q8NER1
Molecular weight:
94955.3
General function:
Not Available
Specific function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)- tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular weight:
127485.8