Showing Compound Card for Tetrahydrozoline (CDB000671)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:50:16 UTC
Updated at2020-11-18 16:35:24 UTC
CannabisDB IDCDB000671
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameTetrahydrozoline
DescriptionTetrahydrozoline (also known as Tetryzoline), a derivative of imidazoline, is found in over-the-counter eye drops and nasal sprays. Other derivatives include naphazoline, oxymetazoline, and xylometazoline. Tetrahydrozoline is an imidazoline derivative and has two enantiomers. It acts as an agonist for alpha-2 adrenoceptor and it is also an imidazoline I-1 receptor agonist. Tetrahydrozoline can be used to treat the redness of the eyes caused by minor irritation due to its alpha-2 agonism. The alpha-2 agonism can also cause dry mouth and sedating effects, during an overdose. Also, in excessive amounts the imidazoline-1 receptor agonism activity of tetrahydrozoline can cause slow heart rate and low blood pressure (PMID: 24666288 ). It has also been identified as a volatile compound found in cannabis samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC13H16N2
Average Molecular Weight200.29
Monoisotopic Molecular Weight200.1313
IUPAC Name2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4,5-dihydro-1H-imidazole
Traditional Name2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4,5-dihydro-1H-imidazole
CAS Registry Number84-22-0
SMILES
C1CN=C(N1)[C@@H]1CCCC2=CC=CC=C12
InChI Identifier
InChI=1S/C13H16N2/c1-2-6-11-10(4-1)5-3-7-12(11)13-14-8-9-15-13/h1-2,4,6,12H,3,5,7-9H2,(H,14,15)/t12-/m1/s1
InChI KeyBYJAVTDNIXVSPW-GFCCVEGCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Imidolactam
  • 2-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen 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
logP3.11ALOGPS
logP2.24ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.48 m³·mol⁻¹ChemAxon
Polarizability22.92 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-MSTetrahydrozoline, 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
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-2A adrenergic receptorADRA2A10q24-q26P08913 details
Alpha-2B adrenergic receptorADRA2B2p13-q13P18089 details
Alpha-2C adrenergic receptorADRA2C4p16P18825 details
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 ID624897
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound716126
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Lowry JA, Brown JT: Significance of the imidazoline receptors in toxicology. Clin Toxicol (Phila). 2014 Jun;52(5):454-69. doi: 10.3109/15563650.2014.898770. Epub 2014 Mar 25. [PubMed:24666288 ]
  2. 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 ]

Enzymes

Enzyme Details
1. Alpha-2A adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
Enzyme Details
2. Alpha-2B adrenergic receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1