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A8800

Sigma-Aldrich

Alprazolam

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H13ClN4
CAS Number:
28981-97-7
Molecular Weight:
308.76
EC Number:
249-349-2
MDL number:
MFCD00078881
UNSPSC Code:
12352200
PubChem Substance ID:
24891366
NACRES:
NA.77

form

powder

Quality Level

200

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

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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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
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
J M Jonas et al.
The Journal of clinical psychiatry, 54 Suppl, 25-45 (1993-10-01)
A review of the worldwide published literature was conducted to assess the efficacy and safety of alprazolam for the treatment of anxiety disorders, panic disorder, and depression in comparison with those of other active drugs (including other benzodiazepines and antidepressant
J O Cole et al.
The Journal of clinical psychiatry, 54 Suppl, 49-61 (1993-10-01)
A review of the published case reports of adverse behavioral episodes or unexpected psychopathology in patients taking benzodiazepines was undertaken in an attempt to determine if these adverse or unexpected events are more likely to occur with alprazolam when compared
E M Sellers et al.
The Journal of clinical psychiatry, 54 Suppl, 64-75 (1993-10-01)
The incidence of nonmedical use of alprazolam is very low relative to its widespread legitimate medical use; in fact, given the millions of patients who have received this medication, the incidence is remarkably small. In particular, among patients with anxiety
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