Showing Compound Card for 1,7-Dimethyl-beta-carboline (CDB005755)

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Record Information
Version1.0
Created at2020-04-27 16:52:29 UTC
Updated at2021-01-04 18:49:14 UTC
CannabisDB IDCDB005755
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,7-Dimethyl-beta-carboline
Description1,7-Dimethyl-beta-carboline is a dimethylated derivative of beta-carboline and is one of several structural isomers of dimethyl-beta-carboline wherein two methyl groups are substituted at different positions of beta-carboline. More formally, 1,7-Dimethyl-beta-carboline belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. There are three different isomers of carbolines – alpha, beta and gamma. They differ in the position of the nitrogen in the pyridine ring attached to the indole core, with the alpha isoform having the pyridine nitrogen closest to the indole nitrogen and the gamma isoform have the pyridine nitrogen furthest from the indole nitrogen. Beta-carboline alkaloids are widespread in plants and animals, and frequently act as GABAA inverse agonists (PMID: 7780638 ). Dimethyl-beta-carbolines are found in cannabis smoke. 1,7-Dimethyl-beta-carboline is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC13H12N2
Average Molecular Weight196.25
Monoisotopic Molecular Weight196.1
IUPAC Name1,7-dimethyl-9H-pyrido[3,4-b]indole
Traditional Name1,7-dimethyl-9H-pyrido[3,4-b]indole
CAS Registry NumberNot Available
SMILES
CC1=CC2=C(C=C1)C1=CC=NC(C)=C1N2
InChI Identifier
InChI=1S/C13H12N2/c1-8-3-4-10-11-5-6-14-9(2)13(11)15-12(10)7-8/h3-7,15H,1-2H3
InChI KeyIGWSJKQTVMTNDK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Indole
  • Indole or derivatives
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.6ALOGPS
logP2.52ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)6.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.95 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1,7-Dimethyl-beta-carboline , 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MSNot Available
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23113594
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44269442
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Im HK, Im WB, Carter DB, McKinley DD: Interaction of beta-carboline inverse agonists for the benzodiazepine site with another site on GABAA receptors. Br J Pharmacol. 1995 Mar;114(5):1040-4. doi: 10.1111/j.1476-5381.1995.tb13310.x. [PubMed:7780638 ]