ContaminantDB: Triazolam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (23)XML

Record Information

Version

1.0

Creation Date

2009-07-05 03:14:44 UTC

Update Date

2026-05-14 16:52:12 UTC

Accession Number

CHEM002090

Identification

Common Name

Triazolam

Class

Small Molecule

Description

Triazolam is only found in individuals that have used or taken this drug. It is withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions. This drug continues to be available in the U.S. Internationally, triazolam is a Schedule IV drug under the Convention on Psychotropic Substances.Benzodiazepines 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 (GABA_A) 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 Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Adjuvant, Anesthesia
Anti-Anxiety Agent
Benzodiazepine
Drug
GABA Modulator
Human Neurotoxin
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Halcion	ChEBI
DEA no. 2887	HMDB
Genpharm brand OF triazolam	HMDB
Apo triazo	HMDB
Apo-triazo	HMDB
Apotex brand OF triazolam	HMDB
Gen triazolam	HMDB
Gerard brand OF triazolam	HMDB
Pfizer brand OF triazolam	HMDB
Gen-triazolam	HMDB
Triazolam pfizer brand	HMDB
Trilam	HMDB

Chemical Formula

C₁₇H₁₂Cl₂N₄

Average Molecular Mass

343.210 g/mol

Monoisotopic Mass

342.044 g/mol

CAS Registry Number

28911-01-5

IUPAC Name

12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene

Traditional Name

triazolam

SMILES

CC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=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 Key

JOFWLTCLBGQGBO-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

triazolobenzodiazepine (CHEBI:9674 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

sedative

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystalline powder (RxList, A308).

Experimental Properties

Property	Value
Melting Point	233-235°C
Boiling Point	Not Available
Solubility	4.53 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	2.94	ALOGPS
logP	2.89	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.08	ChemAxon
pKa (Strongest Basic)	4.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	103.68 m³·mol⁻¹	ChemAxon
Polarizability	34.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8089000000-80a2c04b55ba4ec57f7d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-0019000000-c8c0d3cd9a1976505512	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0019000000-1a48dd0b8ad68d4c7152	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0019000000-299396e073c781434d64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ke9-1393000000-9375b44f5c2300bb98ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0019000000-45c89b536091edda4e23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0029000000-ff0a3ff2d1d3a8b13088	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fai-0390000000-188cc5d505add9b26071	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-66a85ec67775de1bf91b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-66a85ec67775de1bf91b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-1289000000-ce967160c7f8152bf73c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-3ebd0ee81f9052f5a37b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053u-6009000000-48a129158117535fca22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9152000000-8ffd20b7c50c68f2a695	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0imr-4954000000-75bcea16a1182103168f	Spectrum

Toxicity Profile

Route of Exposure

Inhalation; dermal or skin contact; ingestion (MSDS, A308). Bioavailability is 44% (oral) and 53% (sublingual).

Mechanism of Toxicity

Benzodiazepines 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 (GABA_A) 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.

Metabolism

Hepatic. Small amounts of unmetabolized triazolam appear in the urine. Triazolam undergoes hepatic microsomal oxidation to inactive hydroxylated metabolites that are eliminated primarily as glucuronide conjugates (3). Route of Elimination: Triazolam and its metabolites, principally as conjugated glucuronides, which are presumably inactive, are excreted primarily in the urine. Only small amounts of unmetabolized triazolam appear in the urine. The two primary metabolites accounted for 79.9% of urinary excretion. Half Life: 1.5-5.5 hours

Toxicity Values

LD50: >1000 mg/kg (Oral, Mouse) LD50: >5000 mg/kg (Oral, Rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the short-term treatment of insomnia (1).

Minimum Risk Level

Not Available

Health Effects

Following acute overdose, clinical symptoms or manifestations may include sleepiness, which, following larger overdose can range from stage zero to stage one coma. Initially, excitement may be seen as a result of the disinhibition effects of these drugs, which then progresses to central nervous system depression, hypotension, respiratory depression, and coma (2).

Symptoms

Symptoms of overdose include drowsiness, slurred speech, motor inco-ordination, coma, and respiratory depression.

Treatment

Flumazenil, 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)

Concentrations

Not Available

External Links

DrugBank ID

DB00897

HMDB ID

HMDB0015034

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID