Showing Compound Card for Prehnitene (CDB000495)

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Record Information
Version1.0
Created at2020-03-19 00:40:06 UTC
Updated at2020-11-18 16:35:13 UTC
CannabisDB IDCDB000495
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePrehnitene
Description1,2,3,4-tetramethylbenzene also known as Prehnitene or prehnitol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Prehnitene is possibly neutral. A tetramethylbenzene that consists of benzene substituted by methyl groups at positions 1, 2, 3 and 4. It is classified as an aromatic hydrocarbon with the formula C6H2(CH3)4. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Prehnitene is one of three isomers of tetramethylbenzene, the other two being isodurine (1,2,3,5-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene). Industrially, prehnitene can be isolated from the reformed fraction of oil refineries. It may also be produced by methylation of toluene, xylenes and the trimethylbenzenes hemellitene and pseudocumene (doi:10.1002/14356007.a13_227). 1,2,3,4-tetramethylbenzene has been detected as a volatile component of cannabis (PMID: 26657499 ) and, as such, it can also be detected as constituent of marijuana smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
PrehnitolChEBI
Chemical FormulaC10H14
Average Molecular Weight134.22
Monoisotopic Molecular Weight134.1096
IUPAC Name1,2,3,4-tetramethylbenzene
Traditional Name1,2,3,4-tetramethylbenzene
CAS Registry NumberNot Available
SMILES
CC1=C(C)C(C)=C(C)C=C1
InChI Identifier
InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3
InChI KeyUOHMMEJUHBCKEE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.07ALOGPS
logP4.03ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.22 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPrehnitene, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-28da1a5b7cbbccda1f38Spectrum
GC-MSPrehnitene, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-72f3f4dc86cbc594259eSpectrum
GC-MSPrehnitene, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-28da1a5b7cbbccda1f38Spectrum
GC-MSPrehnitene, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-72f3f4dc86cbc594259eSpectrum
Predicted GC-MSPrehnitene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3900000000-74a8e03648e32bae639eSpectrum
Predicted GC-MSPrehnitene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-4611abcb869468b1fa702016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-06a4fe1a9da3ac5427c42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9300000000-f3cb280395f8494e693c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-05d9aa7c63c8c1b8b31e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-19fdd4802bab4898a43f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2900000000-974e18eb3001abf2957e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-5900000000-10777b22ab7f07472f402021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9500000000-07776fd135790c8873202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-98b28b6b012c48e625142021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-4ca7c509cbbe24c884882021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0059823
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 LinkTetramethylbenzenes
METLIN IDNot Available
PubChem Compound10263
PDB IDNot Available
ChEBI ID38997
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]