You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:17 UTC
HMDB IDHMDB0014417
Secondary Accession Numbers
  • HMDB14417
Metabolite Identification
Common NameBetazole
DescriptionBetazole is only found in individuals that have used or taken this drug. It is a histamine H2 agonist used clinically to test gastric secretory function. [PubChem]Betazole is a histamine analogue. It produces the same effects as histamine, binding the H2 receptor which is a mediator of gastric acid secretion. This agonist action thereby results in an increase in the volume of gastric acid produced.
Structure
Thumb
Synonyms
ValueSource
1H-Pyrazole-3-ethanamineChEBI
2-(1H-Pyrazol-5-yl)ethanamineChEBI
2-(3-Pyrazolyl)ethylamineChEBI
3-(2-Aminoethyl)pyrazoleChEBI
3-(beta-Aminoethyl)pyrazoleChEBI
AmetazoleChEBI
BetazolChEBI
BetazolumChEBI
3-(b-Aminoethyl)pyrazoleGenerator
3-(β-aminoethyl)pyrazoleGenerator
BetazoloHMDB
HistalogMeSH
96791, LillyMeSH
Lilly 96791MeSH
Betazole monohydrochlorideMeSH
Monohydrochloride, betazoleMeSH
Betazole dihydrochlorideMeSH
Dihydrochloride, betazoleMeSH
Chemical FormulaC5H9N3
Average Molecular Weight111.1451
Monoisotopic Molecular Weight111.079647303
IUPAC Name2-(1H-pyrazol-5-yl)ethan-1-amine
Traditional Namehistalog
CAS Registry Number105-20-4
SMILES
NCCC1=CC=NN1
InChI Identifier
InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8)
InChI KeyJXDFEQONERDKSS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct Parent2-arylethylamines
Alternative Parents
Substituents
  • 2-arylethylamine
  • Aralkylamine
  • Heteroaromatic compound
  • Pyrazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility156 g/LNot Available
LogP0.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP-0.64ALOGPS
logP-0.62ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)14.52ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.96 m³·mol⁻¹ChemAxon
Polarizability11.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-144d0789347be85058acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-245730fe6d0d4e90f1dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-69d468c0dea5b77244dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsm-9000000000-2275939f329101dfa9e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-34b105a4b07c16f2545aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9100000000-caccac086c4351bb210dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-59c035c253039c9bded4View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Betazole Action PathwayPw000713Pw000713 greyscalePw000713 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00272 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00272 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00272
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7455
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBetazole
METLIN IDNot Available
PubChem Compound7741
PDB IDNot Available
ChEBI ID59170
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and differentiation. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase and, through a separate G protein-dependent mechanism, the phosphoinositide/protein kinase (PKC) signaling pathway
Gene Name:
HRH2
Uniprot ID:
P25021
Molecular weight:
40097.7
References
  1. Hammond JB, Offen WW: Effect of nizatidine and cimetidine on betazole-stimulated gastric secretion of normal subjects: comparison of effects on acid, water, and pepsin. Am J Gastroenterol. 1988 Jan;83(1):32-6. [PubMed:2892392 ]
  2. Leth R, Elander B, Haglund U, Olbe L, Fellenius E: Histamine H2-receptor of human and rabbit parietal cells. Am J Physiol. 1987 Oct;253(4 Pt 1):G497-501. [PubMed:3661710 ]
  3. Katz LB, Tobia AJ, Shriver DA: Effects of ORF 17583, other histamine H2-receptor antagonists and omeprazole on gastric acid secretory states in rats and dogs. J Pharmacol Exp Ther. 1987 Aug;242(2):437-42. [PubMed:2886642 ]
  4. Katz LB, Scott CK, Shriver DA: Pharmacological comparison of ORF 17910, a potent, long-acting histamine H2-receptor antagonist, to cimetidine and ranitidine. J Pharmacol Exp Ther. 1986 Aug;238(2):587-93. [PubMed:2874214 ]
  5. Ribeiro TC, Salgado JA, Castro Lde P: Effect of cimetidine on basal and betazole-stimulated gastric acid secretion in peptic ulcer. Arq Gastroenterol. 1980 Jan-Mar;17(1):4-6. [PubMed:7213132 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]