Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:09 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
Data?1676999889
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
HistalogHMDB
96791, LillyHMDB
Lilly 96791HMDB
Betazole monohydrochlorideHMDB
Monohydrochloride, betazoleHMDB
Betazole dihydrochlorideHMDB
Dihydrochloride, betazoleHMDB
Chemical FormulaC5H9N3
Average Molecular Weight111.1451
Monoisotopic Molecular Weight111.079647303
IUPAC Name2-(1H-pyrazol-3-yl)ethan-1-amine
Traditional Namebetazole
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
Description Belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility156 g/LNot Available
LogP0.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility156 g/LALOGPS
logP-0.64ALOGPS
logP-0.28ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)9.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.4 m³·mol⁻¹ChemAxon
Polarizability12.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.97731661259
DarkChem[M-H]-115.97431661259
DeepCCS[M+H]+122.18230932474
DeepCCS[M-H]-120.01930932474
DeepCCS[M-2H]-155.87130932474
DeepCCS[M+Na]+130.32930932474
AllCCS[M+H]+124.132859911
AllCCS[M+H-H2O]+119.232859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.932859911
AllCCS[M-H]-122.532859911
AllCCS[M+Na-2H]-125.032859911
AllCCS[M+HCOO]-127.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BetazoleNCCC1=CC=NN12242.4Standard polar33892256
BetazoleNCCC1=CC=NN11335.1Standard non polar33892256
BetazoleNCCC1=CC=NN11299.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Betazole,1TMS,isomer #1C[Si](C)(C)NCCC1=CC=N[NH]11456.0Semi standard non polar33892256
Betazole,1TMS,isomer #1C[Si](C)(C)NCCC1=CC=N[NH]11522.3Standard non polar33892256
Betazole,1TMS,isomer #1C[Si](C)(C)NCCC1=CC=N[NH]11939.9Standard polar33892256
Betazole,1TMS,isomer #2C[Si](C)(C)N1N=CC=C1CCN1331.1Semi standard non polar33892256
Betazole,1TMS,isomer #2C[Si](C)(C)N1N=CC=C1CCN1369.5Standard non polar33892256
Betazole,1TMS,isomer #2C[Si](C)(C)N1N=CC=C1CCN2045.3Standard polar33892256
Betazole,2TMS,isomer #1C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C1686.9Semi standard non polar33892256
Betazole,2TMS,isomer #1C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C1717.4Standard non polar33892256
Betazole,2TMS,isomer #1C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C1919.5Standard polar33892256
Betazole,2TMS,isomer #2C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C1465.1Semi standard non polar33892256
Betazole,2TMS,isomer #2C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C1522.0Standard non polar33892256
Betazole,2TMS,isomer #2C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C1743.5Standard polar33892256
Betazole,3TMS,isomer #1C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C1735.0Semi standard non polar33892256
Betazole,3TMS,isomer #1C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C1731.4Standard non polar33892256
Betazole,3TMS,isomer #1C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C1716.9Standard polar33892256
Betazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]11674.3Semi standard non polar33892256
Betazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]11780.7Standard non polar33892256
Betazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]12076.8Standard polar33892256
Betazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1N=CC=C1CCN1566.8Semi standard non polar33892256
Betazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1N=CC=C1CCN1573.7Standard non polar33892256
Betazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1N=CC=C1CCN2064.2Standard polar33892256
Betazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C2062.3Semi standard non polar33892256
Betazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C2169.8Standard non polar33892256
Betazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C2084.8Standard polar33892256
Betazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C1922.6Semi standard non polar33892256
Betazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C1958.1Standard non polar33892256
Betazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C1907.4Standard polar33892256
Betazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2340.0Semi standard non polar33892256
Betazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2339.6Standard non polar33892256
Betazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2015.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Betazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-144d0789347be85058ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betazole 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 - Betazole 10V, Positive-QTOFsplash10-03dj-9700000000-245730fe6d0d4e90f1db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 20V, Positive-QTOFsplash10-0002-9100000000-69d468c0dea5b77244df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 40V, Positive-QTOFsplash10-0fsm-9000000000-2275939f329101dfa9e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 10V, Negative-QTOFsplash10-03di-5900000000-34b105a4b07c16f2545a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 20V, Negative-QTOFsplash10-001i-9100000000-caccac086c4351bb210d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 40V, Negative-QTOFsplash10-00kf-9000000000-59c035c253039c9bded42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 10V, Negative-QTOFsplash10-03di-1900000000-3c631a8474f0703c20f42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 20V, Negative-QTOFsplash10-03xr-9700000000-4e1326cbdac93fd794532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 40V, Negative-QTOFsplash10-014i-9000000000-8c45be4ff6589f405da52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 10V, Positive-QTOFsplash10-01ot-9500000000-1d2e4a9ebebec2ee813a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 20V, Positive-QTOFsplash10-0002-9000000000-395e58e953294363f4b02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betazole 40V, Positive-QTOFsplash10-016r-9000000000-bb079d3ac1740db526d82021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00272 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00272 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00272
Phenol Explorer Compound IDNot Available
FooDB 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
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 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 ]