Showing Compound Card for Dyclocaine (CDB000599)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-03-19 00:45:54 UTC
Updated at2020-12-07 19:07:34 UTC
CannabisDB IDCDB000599
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDyclocaine
DescriptionDyclocaine or Dyclonine, also known as diclonina or dycloninum, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by an alkyl and a phenyl group. Dyclocaine is a potentially toxic compound. It is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray. Dyclonine is only found in individuals that have used or taken this drug. Dyclonine blocks both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanoneChEBI
2-(1-Piperidyl)ethyl p-butoxyphenyl ketoneChEBI
3-Piperidino-4'-butoxypropiophenoneChEBI
4'-Butoxy-3-piperidinopropiophenoneChEBI
4-Butoxy-beta-piperidinopropiophenoneChEBI
4-N-Butoxy-beta-(1-piperidyl)propiophenoneChEBI
DicloninaChEBI
DycloninumChEBI
4-Butoxy-b-piperidinopropiophenoneGenerator
4-Butoxy-β-piperidinopropiophenoneGenerator
4-N-Butoxy-b-(1-piperidyl)propiophenoneGenerator
4-N-Butoxy-β-(1-piperidyl)propiophenoneGenerator
SucretsHMDB
TanacHMDB
DycloneHMDB
Dyclonine hydrochlorideHMDB
Dyclonine HCLHMDB
Chemical FormulaC18H27NO2
Average Molecular Weight289.41
Monoisotopic Molecular Weight289.2042
IUPAC Name1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one
Traditional Namedyclonine
CAS Registry Number586-60-7
SMILES
CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1
InChI Identifier
InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3
InChI KeyBZEWSEKUUPWQDQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Piperidine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
logP4.11ALOGPS
logP3.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.07 m³·mol⁻¹ChemAxon
Polarizability35.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDyclocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-9440000000-a86aac6d96e16aac8d02Spectrum
Predicted GC-MSDyclocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2190000000-c5e926d926da3f6e33872016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-9550000000-f1734edb24416808a4782016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-ff38128b39bd16ebc42f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-0e2e4e5faddcfc83f1762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4290000000-9b6e8d8e9f7264d8fc3e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9410000000-199b90aa399041a2e4222016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-dab0be3d01712a81a5442021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3190000000-98054ac06c2da05754e92021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-6e97375e29bf89aba1e82021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f9f84a09fd9aec8817232021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0290000000-c1c0c098612ca42e1f5a2021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0081-0910000000-ebee0fba4bb1c6af25df2021-10-11View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Sodium channel protein type 10 subunit alphaSCN10A3p22.2Q9Y5Y9 details
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0014783
DrugBank IDDB00645
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3068
KEGG Compound IDC07881
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDyclonine
METLIN IDNot Available
PubChem Compound3180
PDB IDNot Available
ChEBI ID4724
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 ]

Transporters

Enzyme Details
1. Sodium channel protein type 10 subunit alpha
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6