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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:10:06 UTC
Update Date2019-07-23 07:15:29 UTC
HMDB IDHMDB0060969
Secondary Accession Numbers
  • HMDB60969
Metabolite Identification
Common Namedesmethyladinazolam
Descriptiondesmethyladinazolam belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring. desmethyladinazolam is a very strong basic compound (based on its pKa). desmethyladinazolam is a metabolite of adinazolam. Adinazolam (marketed under the brand name Deracyn) is a benzodiazepine derivative. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties.
Structure
Data?1563866129
SynonymsNot Available
Chemical FormulaC17H14ClN5
Average Molecular Weight323.78
Monoisotopic Molecular Weight323.09377318
IUPAC Name{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine
Traditional Name{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanamine
CAS Registry NumberNot Available
SMILES
NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
InChI Identifier
InChI=1S/C17H14ClN5/c18-12-6-7-14-13(8-12)17(11-4-2-1-3-5-11)20-10-16-22-21-15(9-19)23(14)16/h1-8H,9-10,19H2
InChI KeyIITNCTOGXYNNRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • 1,2,4-triazolo[4,3-a][1,4]benzodiazepine
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Imine
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.072 g/LALOGPS
logP1.62ALOGPS
logP1.47ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)7.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.24 m³·mol⁻¹ChemAxon
Polarizability33.42 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-205.85530932474
DeepCCS[M+Na]+181.08130932474
AllCCS[M+H]+174.732859911
AllCCS[M+H-H2O]+171.332859911
AllCCS[M+NH4]+177.832859911
AllCCS[M+Na]+178.732859911
AllCCS[M-H]-177.132859911
AllCCS[M+Na-2H]-176.332859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
desmethyladinazolamNCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N124213.2Standard polar33892256
desmethyladinazolamNCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N123072.0Standard non polar33892256
desmethyladinazolamNCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N123092.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
desmethyladinazolam,1TMS,isomer #1C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N213193.7Semi standard non polar33892256
desmethyladinazolam,1TMS,isomer #1C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N213071.9Standard non polar33892256
desmethyladinazolam,1TMS,isomer #1C[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N214506.7Standard polar33892256
desmethyladinazolam,2TMS,isomer #1C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C3194.6Semi standard non polar33892256
desmethyladinazolam,2TMS,isomer #1C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C3285.9Standard non polar33892256
desmethyladinazolam,2TMS,isomer #1C[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C4298.5Standard polar33892256
desmethyladinazolam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N213356.3Semi standard non polar33892256
desmethyladinazolam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N213312.9Standard non polar33892256
desmethyladinazolam,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N214558.4Standard polar33892256
desmethyladinazolam,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C3541.1Semi standard non polar33892256
desmethyladinazolam,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C3740.6Standard non polar33892256
desmethyladinazolam,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=NN=C2CN=C(C3=CC=CC=C3)C3=CC(Cl)=CC=C3N21)[Si](C)(C)C(C)(C)C4340.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - desmethyladinazolam GC-MS (Non-derivatized) - 70eV, Positivesplash10-053v-6092000000-6eecf8822b2572c1b12c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - desmethyladinazolam 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 - desmethyladinazolam 10V, Positive-QTOFsplash10-00di-0009000000-383cca510ff73d94aece2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Positive-QTOFsplash10-05fr-0019000000-ac89e8cd06fcf4dca7292017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Positive-QTOFsplash10-0i00-5491000000-92f0352d7a746554fd1d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Negative-QTOFsplash10-00di-0039000000-3a5e88caae0c6b1364f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Negative-QTOFsplash10-00di-0069000000-e065989320309b0956d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Negative-QTOFsplash10-0udi-5291000000-134c23efc70b9e9534d02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Negative-QTOFsplash10-00di-0009000000-240e75f736e0def15d642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Negative-QTOFsplash10-00di-1029000000-115ac79998dbe2a94e202021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Negative-QTOFsplash10-0kai-5095000000-4ea2f9c74da54774cf002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 10V, Positive-QTOFsplash10-00di-0009000000-43ea0644a7793b861ac22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 20V, Positive-QTOFsplash10-00di-0009000000-202c5e39f130150291e32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - desmethyladinazolam 40V, Positive-QTOFsplash10-0pxu-4491000000-d374db1e9979915019db2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12611937
PDB IDNot Available
ChEBI IDNot Available
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