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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:09 UTC

HMDB ID

HMDB0014417

Secondary Accession Numbers

HMDB14417

Metabolite Identification

Common Name

Betazole

Description

Betazole 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1H-Pyrazole-3-ethanamine	ChEBI
2-(1H-Pyrazol-5-yl)ethanamine	ChEBI
2-(3-Pyrazolyl)ethylamine	ChEBI
3-(2-Aminoethyl)pyrazole	ChEBI
3-(beta-Aminoethyl)pyrazole	ChEBI
Ametazole	ChEBI
Betazol	ChEBI
Betazolum	ChEBI
3-(b-Aminoethyl)pyrazole	Generator
3-(Β-aminoethyl)pyrazole	Generator
Betazolo	HMDB
Histalog	HMDB
96791, Lilly	HMDB
Lilly 96791	HMDB
Betazole monohydrochloride	HMDB
Monohydrochloride, betazole	HMDB
Betazole dihydrochloride	HMDB
Dihydrochloride, betazole	HMDB

Chemical Formula

C₅H₉N₃

Average Molecular Weight

111.1451

Monoisotopic Molecular Weight

111.079647303

IUPAC Name

2-(1H-pyrazol-3-yl)ethan-1-amine

Traditional Name

betazole

CAS Registry Number

105-20-4

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 Key

JXDFEQONERDKSS-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

2-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:59170 )
primary amino compound (CHEBI:59170 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (PMID: 19167006)

Cellular substructure

Membrane (HMDB: HMDB0014417)

Source

Exogenous

Exogenous (HMDB: HMDB0014417)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Betazole Action Pathway (PathBank: SMP0000736)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	156 g/L	Not Available
LogP	0.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	156 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-0.28	ChemAxon
logS	0.15	ALOGPS
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	9.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.4 m³·mol⁻¹	ChemAxon
Polarizability	12.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	119.977	31661259
DarkChem	[M-H]-	115.974	31661259
DeepCCS	[M+H]+	122.182	30932474
DeepCCS	[M-H]-	120.019	30932474
DeepCCS	[M-2H]-	155.871	30932474
DeepCCS	[M+Na]+	130.329	30932474
AllCCS	[M+H]+	124.1	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	128.6	32859911
AllCCS	[M+Na]+	129.9	32859911
AllCCS	[M-H]-	122.5	32859911
AllCCS	[M+Na-2H]-	125.0	32859911
AllCCS	[M+HCOO]-	127.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Betazole	NCCC1=CC=NN1	2242.4	Standard polar	33892256
Betazole	NCCC1=CC=NN1	1335.1	Standard non polar	33892256
Betazole	NCCC1=CC=NN1	1299.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Betazole,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC=N[NH]1	1456.0	Semi standard non polar	33892256
Betazole,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC=N[NH]1	1522.3	Standard non polar	33892256
Betazole,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC=N[NH]1	1939.9	Standard polar	33892256
Betazole,1TMS,isomer #2	C[Si](C)(C)N1N=CC=C1CCN	1331.1	Semi standard non polar	33892256
Betazole,1TMS,isomer #2	C[Si](C)(C)N1N=CC=C1CCN	1369.5	Standard non polar	33892256
Betazole,1TMS,isomer #2	C[Si](C)(C)N1N=CC=C1CCN	2045.3	Standard polar	33892256
Betazole,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C	1686.9	Semi standard non polar	33892256
Betazole,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C	1717.4	Standard non polar	33892256
Betazole,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C	1919.5	Standard polar	33892256
Betazole,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C	1465.1	Semi standard non polar	33892256
Betazole,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C	1522.0	Standard non polar	33892256
Betazole,2TMS,isomer #2	C[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C	1743.5	Standard polar	33892256
Betazole,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C	1735.0	Semi standard non polar	33892256
Betazole,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C	1731.4	Standard non polar	33892256
Betazole,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C)[Si](C)(C)C	1716.9	Standard polar	33892256
Betazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]1	1674.3	Semi standard non polar	33892256
Betazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]1	1780.7	Standard non polar	33892256
Betazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC=N[NH]1	2076.8	Standard polar	33892256
Betazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1N=CC=C1CCN	1566.8	Semi standard non polar	33892256
Betazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1N=CC=C1CCN	1573.7	Standard non polar	33892256
Betazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1N=CC=C1CCN	2064.2	Standard polar	33892256
Betazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C	2062.3	Semi standard non polar	33892256
Betazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C	2169.8	Standard non polar	33892256
Betazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=N[NH]1)[Si](C)(C)C(C)(C)C	2084.8	Standard polar	33892256
Betazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C	1922.6	Semi standard non polar	33892256
Betazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C	1958.1	Standard non polar	33892256
Betazole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC=NN1[Si](C)(C)C(C)(C)C	1907.4	Standard polar	33892256
Betazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2340.0	Semi standard non polar	33892256
Betazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2339.6	Standard non polar	33892256
Betazole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=NN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2015.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Betazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-144d0789347be85058ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Betazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Betazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 10V, Positive-QTOF	splash10-03dj-9700000000-245730fe6d0d4e90f1db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 20V, Positive-QTOF	splash10-0002-9100000000-69d468c0dea5b77244df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 40V, Positive-QTOF	splash10-0fsm-9000000000-2275939f329101dfa9e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 10V, Negative-QTOF	splash10-03di-5900000000-34b105a4b07c16f2545a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 20V, Negative-QTOF	splash10-001i-9100000000-caccac086c4351bb210d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 40V, Negative-QTOF	splash10-00kf-9000000000-59c035c253039c9bded4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 10V, Negative-QTOF	splash10-03di-1900000000-3c631a8474f0703c20f4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 20V, Negative-QTOF	splash10-03xr-9700000000-4e1326cbdac93fd79453	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 40V, Negative-QTOF	splash10-014i-9000000000-8c45be4ff6589f405da5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 10V, Positive-QTOF	splash10-01ot-9500000000-1d2e4a9ebebec2ee813a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 20V, Positive-QTOF	splash10-0002-9000000000-395e58e953294363f4b0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betazole 40V, Positive-QTOF	splash10-016r-9000000000-bb079d3ac1740db526d8	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Betazole Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00272	21059682	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00272	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00272

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Betazole

METLIN ID

Not Available

PubChem Compound

7741

PDB ID

Not Available

ChEBI ID

59170

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Histamine H2 receptor

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

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 ]
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 ]
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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Betazole (HMDB0014417)

MOL for HMDB0014417 (Betazole)

3D MOL for HMDB0014417 (Betazole)

3D SDF for HMDB0014417 (Betazole)

3D-SDF for HMDB0014417 (Betazole)

PDB for HMDB0014417 (Betazole)

3D PDB for HMDB0014417 (Betazole)

SMILES for HMDB0014417 (Betazole)

INCHI for HMDB0014417 (Betazole)

Structure for HMDB0014417 (Betazole)

3D Structure for HMDB0014417 (Betazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References