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A8800

Sigma-Aldrich

Alprazolam

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Synonym(s):
8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
Empirical Formula (Hill Notation):
C17H13ClN4
CAS Number:
Molecular Weight:
308.76
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

solubility

H2O: insoluble
methanol: soluble

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

originator

Johnson & Johnson

SMILES string

Cc1nnc2CN=C(c3ccccc3)c4cc(Cl)ccc4-n12

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 key

VREFGVBLTWBCJP-UHFFFAOYSA-N

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1 of 4

This Item
A0357000D0899E3638
vibrant-m

A8800

Alprazolam

vibrant-m

A0357000

Alprazolam

vibrant-m

D0899

Diazepam

vibrant-m

E3638

Estazolam

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

form

powder

form

-

form

powder

form

-

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

200

originator

Johnson & Johnson

originator

-

originator

Roche

originator

Abbott

solubility

H2O: insoluble, methanol: soluble

solubility

-

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.6 mg/mL, DMF: soluble, H2O: slightly soluble, ethanol: soluble

solubility

-

General description

Alprazolam is a triazole-containing benzodiazepine that is related to diazepam and other 1,4-benxodiazepines. Like other benzodiazepines, Alprazolam is a GABAergic agonist that modulates GABAA receptors. GABAA receptors in the central nervous system are ligand-gated ion channels that are bound by the stimulatory neurotransmitter GABA; binding of this ligand allows ion movement through the channel and results in neurotransmission inhibition.

Biochem/physiol Actions

Alprazolam binds the GABAA receptor at the benzodiazepine site, which is different than the ligand-binding site at which GABA binds. Alprazolam has been shown to be an anxiolytic (anti-anxiety agent) as well as having anticonvulsant, muscle relaxant and antidepressant activity.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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An Overview of the CNS-Pharmacodynamic Profiles of Nonselective and Selective GABA Agonists
Chen, X., et al.
Advances in Pharmacological Sciences, 2012, 1-10 (2012)
G W Dawson et al.
Drugs, 27(2), 132-147 (1984-02-01)
Alprazolam is a triazolobenzodiazepine which is related to diazepam and other 1,4-benzodiazepines, and has a similar pharmacological profile. Relative to the newer benzodiazepines, alprazolam has an intermediate half-life of 10 to 12 hours in healthy young subjects. In placebo-controlled and
Angela C Rintoul et al.
The Medical journal of Australia, 198(4), 206-209 (2013-03-05)
To examine the rate of detection of alprazolam among cases of heroin-related death (HRD) in Victoria, including the relationship between alprazolam supply and HRDs. Population-based study of community alprazolam supply in Victoria and HRDs reported to the Victorian coroner from
Gary G Kay et al.
Postgraduate medicine, 124(3), 7-15 (2012-06-14)
To evaluate the cognitive effects of fesoterodine 4 and 8 mg versus placebo in healthy older adults. This was an active- and placebo-controlled, double-blind, double-dummy crossover study conducted using healthy volunteers (aged 65-85 years) with baseline Mini-Mental State Examination score
Geoffrey K Isbister et al.
British journal of clinical pharmacology, 58(1), 88-95 (2004-06-23)
To describe alprazolam poisoning and the relative toxicity of alprazolam compared with other benzodiazepines. A database of consecutive poisoning admissions to a regional toxicology service was searched to identify consecutive benzodiazepine deliberate self poisonings, which were coded as alprazolam, diazepam

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