Showing Compound Card for 2,4-Dimethyl-3-ethylpyrrole (CDB005666)

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Record Information
Version1.0
Created at2020-04-27 16:43:33 UTC
Updated at2021-01-04 18:49:05 UTC
CannabisDB IDCDB005666
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,4-Dimethyl-3-ethylpyrrole
Description2,4-Dimethyl-3-ethylpyrrole, also known as kryptopyrrole is an alkylpyrrole and one of several alkylated derivatives of pyrrole. It belongs to the class of organic compounds known as substituted pyrroles. These are heterocyclic compounds containing a pyrrole ring substituted at one or more positions. 2,4-Dimethyl-3-ethylpyrrole is one of several structural isomers of dimethylethylpyrrole wherein the ethyl and two methyl groups are substituted at different positions of the pyrrole ring. Kryptopyrrole has been found to be present in the urine of patients with hereditary hepatic porphyria (PMID: 1277751 ). Increases in pyrrole levels and excretion may occur as a result of stress-induced changes in intestinal permeability, which in turn leads to increased pyrrole absorption. Dimethylethylpyrroles are found in cannabis smoke. 2,4-Dimethyl-3-ethylpyrrole is formed during the combustion of cannabis ( Ref:DOI )
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
KryptopyrroleMeSH
2,4-Dimethyl-3-ethylpyrroleMeSH
Chemical FormulaC8H13N
Average Molecular Weight123.2
Monoisotopic Molecular Weight123.1048
IUPAC Name3-ethyl-2,4-dimethyl-1H-pyrrole
Traditional Name3-ethyl-2,4-dimethyl-1H-pyrrole
CAS Registry Number517-22-6
SMILES
CCC1=C(C)NC=C1C
InChI Identifier
InChI=1S/C8H13N/c1-4-8-6(2)5-9-7(8)3/h5,9H,4H2,1-3H3
InChI KeyZEBBLOXDLGIMEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as substituted pyrroles. These are heterocyclic compounds containing a pyrrole ring substituted at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentSubstituted pyrroles
Alternative Parents
Substituents
  • Substituted pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP2.69ALOGPS
logP2.72ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)18.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.65 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,4-Dimethyl-3-ethylpyrrole, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
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 ID10155
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10600
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Brodie MJ, Graham DJ, Thompson GG, Moore MR, Goldberg A: The porphyrinogenic effects of kryptopyrrole in the rat and the occurrence of urinary kryptopyrrole in human hereditary hepatic porphyria. Clin Sci Mol Med. 1976 May;50(5):431-4. doi: 10.1042/cs0500431. [PubMed:1277751 ]