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Merck
CN

T9772

Sigma-Aldrich

Triazolam

Synonym(s):

8-Chloro-6-[2-chlorophenyl]-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

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About This Item

Empirical Formula (Hill Notation):
C17H12Cl2N4
CAS Number:
28911-01-5
Molecular Weight:
343.21
EC Number:
249-307-3
MDL number:
MFCD00079623
UNSPSC Code:
12352200
PubChem Substance ID:
24900602
NACRES:
NA.77

Key Documents

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drug control

USDEA Schedule IV; Home Office Schedule 4.1; psychotrope (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IV (Portugal); Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet
kontrollierte Droge in Deutschland

solubility

0.1 M HCl: soluble 1 g in 600 mL solvent
chloroform: soluble 1 g in 25 mL solvent
ethanol: soluble 1 g in 1000 mL solvent
DMSO: soluble 5.4 mg/mL
dichloromethane: 50 mg/mL, clear, colorless to faintly yellow
methanol: soluble 8.8 mg/mL
H2O: insoluble
diethyl ether: insoluble

originator

Johnson & Johnson

SMILES string

ClC1=CC=CC=C1C2=NCC3=NN=C(C)N3C4=CC=C(Cl)C=C42

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

Gene Information

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879)

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Application

Triazolam has been used to define nonspecific binding in radioligand binding assays. Triazolam has also been used to study the effects of reducing mPer1 mRNA levels in mouse cerbellum.

Biochem/physiol Actions

Anxiolytic; ligand for the GABAA receptor benzodiazepine modulatory site.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Triazolam is soluble in dichloromethane at 50 mg/ml, with heat as needed, yielding a clear, colorless to faint yellow solution. Furthermore, 1g of triazolam is soluble in 25 mL chloroform, 1000 mL ethanol, and 600 mL 0.1 M HCl. It is also soluble in DMSO (5.4 mg/ml) and methanol (8.8 mg/ml). However, it is insoluble in water and in ether.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
059H0832
127H4125
126H4011
102H4001
067H4076

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R L Voorman et al.
The Journal of pharmacology and experimental therapeutics, 287(1), 381-388 (1998-10-09)
Administration of delavirdine, an HIV-1 reverse transcriptase inhibitor, to rats or monkeys resulted in apparent loss of hepatic microsomal CYP3A and delavirdine desalkylation activity. Human CYP3A catalyzes the formation of desalkyl delavirdine and 6'-hydroxy delavirdine, an unstable metabolite, while CYP2D6
M Akiyama et al.
British journal of pharmacology, 128(7), 1616-1622 (1999-12-22)
1. The mPer1 and mPer2 genes are putative mouse clock genes that regulate circadian oscillator present in the suprachiasmatic nucleus (SCN) neuron. While they are also expressed in the granular cell layer in the cerebellum, their function is unknown. In
Susan K Sullivan et al.
The Journal of pharmacology and experimental therapeutics, 311(2), 537-546 (2004-07-17)
Clinically used benzodiazepine and nonbenzodiazepine sedative-hypnotic agents for the treatment of insomnia produce their therapeutic effects through allosteric enhancement of the effects of the inhibitory neurotransmitter GABA at the GABA(A) receptor. Indiplon is a novel pyrazolopyrimidine sedative-hypnotic agent, currently in
P D Kroboth et al.
Drug intelligence & clinical pharmacy, 17(7-8), 495-500 (1983-07-01)
Triazolam is a sedative/hypnotic triazolobenzodiazepine, structurally related to alprazolam. Recently, it has been approved for the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. Triazolam is metabolized with a half-life of
Guoyou Jin et al.
Talanta, 84(3), 644-650 (2011-04-13)
A triazolam-imprinted silica microsphere was prepared by combining a surface molecular-imprinting technique with the sol-gel process. The results illustrate that the triazolam-imprinted silica microspheres provided using γ-aminopropyltriethoxysilane and phenyltrimethoxysilane as monomers exhibited higher selectivity than those provided from γ-aminopropyltriethoxysilane and
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