Triazolam (CED0004723)

Record Information
Version1.0
Creation Date2009-07-05 03:14:44 UTC
Update Date2026-05-14 16:52:12 UTC
Accession NumberCHEM002090
Identification
Common NameTriazolam
ClassSmall Molecule
Description
Triazolam belongs to the 1,4-benzodiazepines, a subclass of benzodiazepines within the organic compounds. This exogenous compound has the formula C17H12Cl2N4 and an average molecular weight of 343.21 g/mol. At room temperature, it exists as a solid. It is used as a sedative and is found in healthcare, pharmaceuticals, and veterinary products as a hypnotic and sedative. Other recorded sources include food preservation, building and construction materials such as tents, canopies, and ceilings, electrical and electronic equipment including antennas, electrodes, and electrically stimulated smoking devices, and household cleaning and consumer products including perfumes within detergents and soaps, pipe accessories, and cigar cigarettes. The recorded exposure route is oral. Triazolam targets 22 proteins, including the translocator protein (TSPO) and gamma-aminobutyric acid receptor subunits alpha-1 (GABRA1), alpha-2 (GABRA2), alpha-3 (GABRA3), and alpha-4 (GABRA4), among 17 other proteins. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. Because 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 GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Contaminant Type
  • Adjuvant, Anesthesia
  • Anti-Anxiety Agent
  • Benzodiazepine
  • Drug
  • GABA Modulator
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
HalcionChEBI
DEA no. 2887HMDB
Genpharm brand OF triazolamHMDB
Apo triazoHMDB
Apo-triazoHMDB
Apotex brand OF triazolamHMDB
Gen triazolamHMDB
Gerard brand OF triazolamHMDB
Pfizer brand OF triazolamHMDB
Gen-triazolamHMDB
Triazolam pfizer brandHMDB
TrilamHMDB
Chemical FormulaC17H12Cl2N4
Average Molecular Mass343.210 g/mol
Monoisotopic Mass342.044 g/mol
CAS Registry Number28911-01-5
IUPAC Name12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
Traditional Nametriazolam
SMILESCC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12
InChI IdentifierInChI=1S/C17H12Cl2N4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3
InChI KeyJOFWLTCLBGQGBO-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
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Imine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organohalogen compound
  • Organochloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite crystalline powder (RxList, A308).
Experimental Properties
PropertyValue
Melting Point233-235°C
Boiling PointNot Available
Solubility4.53 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP2.94ALOGPS
logP2.89ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)18.08ChemAxon
pKa (Strongest Basic)4.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity103.68 m³·mol⁻¹ChemAxon
Polarizability34.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-8089000000-80a2c04b55ba4ec57f7dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0019000000-c8c0d3cd9a1976505512Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0019000000-1a48dd0b8ad68d4c7152Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0019000000-299396e073c781434d64Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ke9-1393000000-9375b44f5c2300bb98baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0019000000-45c89b536091edda4e23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0029000000-ff0a3ff2d1d3a8b13088Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fai-0390000000-188cc5d505add9b26071Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-66a85ec67775de1bf91bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-66a85ec67775de1bf91bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-1289000000-ce967160c7f8152bf73cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-3ebd0ee81f9052f5a37bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053u-6009000000-48a129158117535fca22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9152000000-8ffd20b7c50c68f2a695Not AvailableView Spectrum
MSMS Spectrumsplash10-0imr-4954000000-75bcea16a1182103168fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityBenzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects 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 GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include drowsiness, slurred speech, motor inco-ordination, coma, and respiratory depression.
TreatmentFlumazenil, a specific benzodiazepine receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. Prior to the administration of flumazenil, necessary measures should be instituted to secure airway, ventilation and intravenous access. (10)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1000.0mg/kg>1000MouseLD50OralexperimentalNot Available
5000.0mg/kg>5000RatLD50OralexperimentalNot Available
2780.0Log mg/kg[1600:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
376Hypnotics and sedativesHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansPredicted (SEA)0.544945
Gamma-aminobutyric acid receptor subunit alpha-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P47869HumansPredicted (SEA)0.389246
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)61.5009
Gamma-aminobutyric acid receptor subunit alpha-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P34903HumansPredicted (SEA)0.467095
Gamma-aminobutyric acid receptor subunit alpha-5 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-5P31644HumansPredicted (SEA)1.71268
Click to view 3D structureTranslocator proteinP16257Rattus norvegicusPredicted (SEA)2.95827
Mediator of RNA polymerase II transcription subunit 1 structureClick to view 3D structureMediator of RNA polymerase II transcription subunit 1Q15648HumansPredicted (SEA)3.26967
Beta/gamma crystallin domain-containing protein 1 structureClick to view 3D structureBeta/gamma crystallin domain-containing protein 1Q9Y4K1HumansPredicted (SEA)3.26967
Click to view 3D structureHornerinQ86YZ3HumansPredicted (SEA)3.26967
Nuclear factor related to kappa-B-binding protein structureClick to view 3D structureNuclear factor related to kappa-B-binding proteinQ6P4R8HumansPredicted (SEA)3.26967
Cell division cycle-associated protein 2 structureClick to view 3D structureCell division cycle-associated protein 2Q69YH5HumansPredicted (SEA)3.26967
Lymphoid-specific helicase structureClick to view 3D structureLymphoid-specific helicaseQ9NRZ9HumansPredicted (SEA)3.26967
Pre-mRNA 3'-end-processing factor FIP1 structureClick to view 3D structurePre-mRNA 3'-end-processing factor FIP1Q6UN15HumansPredicted (SEA)3.26967
Protein FRG1 structureClick to view 3D structureProtein FRG1Q14331HumansPredicted (SEA)3.26967
Click to view 3D structureArginine and glutamate-rich protein 1Q9NWB6HumansPredicted (SEA)3.26967
Click to view 3D structureG patch domain-containing protein 8Q9UKJ3HumansPredicted (SEA)3.26967
Click to view 3D structureHIRA-interacting protein 3Q9BW71HumansPredicted (SEA)3.26967
Click to view 3D structureBolA-like protein 2Q9H3K6HumansPredicted (SEA)3.26967
Protein SET structureClick to view 3D structureProtein SETQ01105HumansPredicted (SEA)3.26967
Click to view 3D structureCoilinP38432HumansPredicted (SEA)3.26967
Plastin-2 structureClick to view 3D structurePlastin-2P13796HumansPredicted (SEA)3.26967
DNA dC->dU-editing enzyme APOBEC-3C structureClick to view 3D structureDNA dC->dU-editing enzyme APOBEC-3CQ9NRW3HumansPredicted (SEA)3.26967
Histone H2A type 1-D structureClick to view 3D structureHistone H2A type 1-DP20671HumansPredicted (SEA)3.26967
U4/U6 small nuclear ribonucleoprotein Prp31 structureClick to view 3D structureU4/U6 small nuclear ribonucleoprotein Prp31Q8WWY3HumansPredicted (SEA)3.26967
Click to view 3D structureSAP30-binding proteinQ9UHR5HumansPredicted (SEA)3.26967
Gamma-aminobutyric acid receptor subunit alpha-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-1P14867HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-2P47869HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-3P34903HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-6Q16445HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit beta-3 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-3P28472HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-4 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-4P48169HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit alpha-5 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit alpha-5P31644HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit beta-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-1P18505HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit beta-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-2P47870HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit delta structureClick to view 3D structureGamma-aminobutyric acid receptor subunit deltaO14764HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit epsilonP78334HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit gamma-1Q8N1C3HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit gamma-2 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit gamma-2P18507HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit gamma-3Q99928HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit pi structureClick to view 3D structureGamma-aminobutyric acid receptor subunit piO00591HumansKnownNot Available
Gamma-aminobutyric acid receptor subunit rho-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit rho-1P24046HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit rho-2P28476HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit rho-3A8MPY1HumansKnownNot Available
Click to view 3D structureGamma-aminobutyric acid receptor subunit thetaQ9UN88HumansKnownNot Available
Platelet-activating factor receptor structureClick to view 3D structurePlatelet-activating factor receptorP25105HumansKnownNot Available
Gastrin/cholecystokinin type B receptor structureClick to view 3D structureGastrin/cholecystokinin type B receptorP32239HumansKnownNot Available
Click to view 3D structureTranslocator proteinP30536HumansKnownBenzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects 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 GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Concentrations
Not Available
External Links
DrugBank IDDB00897
HMDB IDHMDB0015034
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTriazolam
Chemspider ID5355
ChEBI ID9674
PubChem Compound ID5556
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72.
2. Veje JO, Andersen K, Gjesing S, Kielgast H: [Prescription of tranquilizers and hypnotics in the municipality of Holbaek]. Ugeskr Laeger. 1989 Aug 21;151(34):2134-6.
3. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41.
4. Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51.
5. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8.