Cannabis Compound Database: Showing Compound Card for Betazole (CDB000577)

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Record Information

Version

1.0

Created at

2020-03-19 00:44:39 UTC

Updated at

2020-12-07 19:07:32 UTC

CannabisDB ID

CDB000577

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Betazole

Description

Betazole, also known as histalog or 96791, 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. Betazole is a histamine H2 agonist, which is used clinically to test gastric secretory function. Gastritis can be diagnosed given late absence of gastric acid which is unresponsive to betazole stimulation. In humans, betazole is involved in betazole action pathway. Betazole can be used as a gastric secretory stimulant instead of histamine with the advantage of not provoking side effects and thus not requiring the use of antihistaminic compounds. Betazole is only found in individuals that have used or taken this drug. Surprisingly, betazole has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI

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

111.15

Monoisotopic Molecular Weight

111.0796

IUPAC Name

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

Traditional Name

betazole

CAS Registry Number

105-20-4

SMILES

NCCC1=NNC=C1

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

Disposition

Biological location:

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Betazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9000000000-144d0789347be85058ac	Spectrum
Predicted GC-MS	Betazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Betazole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

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

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Betazole Action Pathway		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Histamine H2 receptor	HRH2	5q35.2	P25021	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Histamine H2 receptor	HRH2	5q35.2	P25021	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0014417

DrugBank ID

DB00272

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

General References

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. 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

Showing Compound Card for Betazole (CDB000577)

Structure for CDB000577 (Betazole)

Enzymes