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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015689
Secondary Accession Numbers
  • HMDB15689
Metabolite Identification
Common NameAntazoline
DescriptionAntazoline is only found in individuals that have used or taken this drug. It is a 1st generation antihistamine that also anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis.Antazoline binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Structure
Data?1582753323
Synonyms
ValueSource
2-(N-Benzylanilinomethyl)-2-imidazolineChEBI
2-(N-Phenyl-N-benzylaminomethyl)imidazolineChEBI
4,5-Dihydro-N-phenyl-N-phenylmethyl-1H-imidazole-2-methanamineChEBI
AntazolinaChEBI
AntazolinumChEBI
PhenazolinHMDB
PhenazolineHMDB
AntistineHMDB
ArithminHMDB
Lannett brand OF antazoline phosphateHMDB
ImidamineHMDB
AntastenHMDB
Antazoline hydrochlorideHMDB
Antazoline phosphateHMDB
AnalergineHMDB
Antazoline phosphate (1:1)HMDB
Hydrochloride, antazolineHMDB
Phosphate, antazolineHMDB
Chemical FormulaC17H19N3
Average Molecular Weight265.3529
Monoisotopic Molecular Weight265.157897623
IUPAC NameN-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
Traditional Nameantazoline
CAS Registry Number91-75-8
SMILES
C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1
InChI Identifier
InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)
InChI KeyREYFJDPCWQRWAA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylbenzamines
Alternative Parents
Substituents
  • Phenylbenzamine
  • Benzylamine
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aralkylamine
  • Imidolactam
  • 2-imidazoline
  • Tertiary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available162.225http://allccs.zhulab.cn/database/detail?ID=AllCCS00000746
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.22ALOGPS
logP2.88ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area27.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.89 m³·mol⁻¹ChemAxon
Polarizability30.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+160.39831661259
DarkChem[M-H]-161.44831661259
DeepCCS[M+H]+159.72830932474
DeepCCS[M-H]-157.33230932474
DeepCCS[M-2H]-190.21630932474
DeepCCS[M+Na]+165.77430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AntazolineC(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN13155.6Standard polar33892256
AntazolineC(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN12213.9Standard non polar33892256
AntazolineC(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN12414.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Antazoline,1TMS,isomer #1C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C12573.0Semi standard non polar33892256
Antazoline,1TMS,isomer #1C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C12449.3Standard non polar33892256
Antazoline,1TMS,isomer #1C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C13445.5Standard polar33892256
Antazoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C12783.8Semi standard non polar33892256
Antazoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C12658.3Standard non polar33892256
Antazoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C13529.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Antazoline EI-B (Non-derivatized)splash10-001i-9000000000-1eb3fa441bd25a0e41a32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antazoline EI-B (Non-derivatized)splash10-001i-9000000000-1eb3fa441bd25a0e41a32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antazoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9520000000-acee1c2b85e17e49b7502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antazoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antazoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 10V, Positive-QTOFsplash10-014i-4290000000-4ac08a84ab740fb2f33e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 20V, Positive-QTOFsplash10-0006-9310000000-cdc9ceb7906b163a79892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 40V, Positive-QTOFsplash10-0006-9000000000-aeb9552d124a58684bc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 10V, Negative-QTOFsplash10-03di-0190000000-2a0590deb8d02d0510f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 20V, Negative-QTOFsplash10-03k9-2590000000-294ec8879dd0fa5e4b8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 40V, Negative-QTOFsplash10-0kcu-7900000000-a5218dce1e2e912dd19e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 10V, Positive-QTOFsplash10-014i-0090000000-7e22bb674a6dd638c95f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 20V, Positive-QTOFsplash10-014i-5190000000-02163279b08dfe80ac6e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 40V, Positive-QTOFsplash10-0006-9000000000-5c02019daf74a4f6ece32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 10V, Negative-QTOFsplash10-03di-0090000000-eb9a3591bd25833346162021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 20V, Negative-QTOFsplash10-001i-3930000000-07adc0d6c79a6a789cfa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antazoline 40V, Negative-QTOFsplash10-0059-8900000000-554f4ffa39078b568dc02021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08799 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB08799 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08799
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntazoline
METLIN IDNot Available
PubChem Compound2200
PDB IDNot Available
ChEBI ID84115
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Figus M, Fogagnolo P, Lazzeri S, Capizzi F, Romagnoli M, Canovetti A, Iester M, Ferreras A, Rossetti L, Nardi M: Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study. Eur J Ophthalmol. 2010 Sep-Oct;20(5):811-8. [PubMed:20383847 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Swiader MJ, Luszczki JJ, Wielosz M, Czuczwar SJ: Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice. Pharmacol Rep. 2005 Jul-Aug;57(4):531-5. [PubMed:16129921 ]