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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014548
Secondary Accession Numbers
  • HMDB14548
Metabolite Identification
Common NameAlprazolam
DescriptionAlprazolam is only found in individuals that have used or taken this drug. It is a triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Structure
Data?1582753191
Synonyms
ValueSource
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineChEBI
XanaxChEBI
TUS-1HMDB
Alphapharm brand OF alprazolamHMDB
Alprazolam orion brandHMDB
Alprazolam pfizer brandHMDB
Apotex brand OF alprazolamHMDB
KalmaHMDB
Kenral brand OF alprazolamHMDB
Nu alprazHMDB
Pfizer brand OF alprazolamHMDB
Temmler brand OF alprazolamHMDB
TrankimazinHMDB
Alprazolam kenral brandHMDB
Alprazolam novopharm brandHMDB
Alprazolam nu-pharm brandHMDB
Apo alprazHMDB
Apo-alprazHMDB
Arzneimittelwerk dresden brand OF alprazolamHMDB
CassadanHMDB
NuAlprazHMDB
Alprazolam alphapharm brandHMDB
ApoAlprazHMDB
Novo alprazolHMDB
Novo-alprazolHMDB
NovoAlprazolHMDB
Nu pharm brand OF alprazolamHMDB
Nu-pharm brand OF alprazolamHMDB
Alprazolam apotex brandHMDB
Alprazolam temmler brandHMDB
AlprazolanHMDB
AlproxHMDB
D-65MTHMDB
D65MTHMDB
EsparonHMDB
Novopharm brand OF alprazolamHMDB
Nu-alprazHMDB
Orion brand OF alprazolamHMDB
RalozamHMDB
TafilHMDB
Chemical FormulaC17H13ClN4
Average Molecular Weight308.765
Monoisotopic Molecular Weight308.082874143
IUPAC Name12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
Traditional Nameneurol
CAS Registry Number28981-97-7
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
InChI Identifier
InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
InChI KeyVREFGVBLTWBCJP-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
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Ketimine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 - 228.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogP4.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM171.530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.23ALOGPS
logP2.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.88 m³·mol⁻¹ChemAxon
Polarizability32.22 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]-201.17930932474
DeepCCS[M+Na]+176.40630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlprazolamCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N123929.3Standard polar33892256
AlprazolamCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N122901.8Standard non polar33892256
AlprazolamCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N122864.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alprazolam GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-4090000000-d08d3360d39ebeeb87f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alprazolam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kdi-4792000000-9f1cdda14e36000955d32014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0910000000-9efa6a8a3dea17fc1ce72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam LC-ESI-QTOF , positive-QTOFsplash10-0a59-0079000000-e4c35fb4df41aa5cc62e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam , positive-QTOFsplash10-0bt9-0169000000-0e6779728f3bdec2acf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam , positive-QTOFsplash10-0a4i-0910000000-9efa6a8a3dea17fc1ce72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam -1V, Positive-QTOFsplash10-0a59-0069000000-a0ce5531f8b2cb70eb282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Alprazolam 35V, Positive-QTOFsplash10-0a59-0097000000-5b89356bc4e59b2029682021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 10V, Positive-QTOFsplash10-0a4i-0009000000-be2bb3a7878fa113efc82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 20V, Positive-QTOFsplash10-0a4i-0039000000-7bd62157388fecd0e4302016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 40V, Positive-QTOFsplash10-0o93-3390000000-307fd2f8dd5a9c4f7eac2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 10V, Negative-QTOFsplash10-0a4i-0029000000-ceec7f24f309605ec6fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 20V, Negative-QTOFsplash10-0a4i-0097000000-d61397bd13173381fc0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 40V, Negative-QTOFsplash10-0udi-3290000000-370bd9e4b8fa73925c042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 10V, Negative-QTOFsplash10-0a4i-0009000000-4c14e6d547df7e93b2042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 20V, Negative-QTOFsplash10-0a4i-0019000000-4e5c057a93f515a3aad62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 40V, Negative-QTOFsplash10-001i-9021000000-63a97e91d4073b1a51cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 10V, Positive-QTOFsplash10-0a4i-0009000000-f3356a9af159cd5dbe122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 20V, Positive-QTOFsplash10-0a4i-0009000000-f3356a9af159cd5dbe122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alprazolam 40V, Positive-QTOFsplash10-004i-1090000000-a69b3052aba45b7146932021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00404 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00404 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00404
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2034
KEGG Compound IDC06817
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlprazolam
METLIN IDNot Available
PubChem Compound2118
PDB IDNot Available
ChEBI ID2611
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 References
  1. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. [PubMed:1686752 ]
  2. Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7. [PubMed:2300914 ]
  3. Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9. [PubMed:2335496 ]
  4. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. [PubMed:9682928 ]
  5. Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8. [PubMed:17453885 ]