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Key Documents

I5773

Sigma-Aldrich

IDRA 21

≥98%

Synonym(s):

7-Chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

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About This Item

Empirical Formula (Hill Notation):
C8H9ClN2O2S
CAS Number:
Molecular Weight:
232.69
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98%

SMILES string

CC1Nc2ccc(Cl)cc2S(=O)(=O)N1

InChI

1S/C8H9ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-5,10-11H,1H3

InChI key

VZRNTCHTJRLTMU-UHFFFAOYSA-N

Biochem/physiol Actions

Blocks the rapid desensitization of the AMPA receptors and markedly prolongs the decay time of the evoked excitatory post-synaptic current.

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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Amy C Arai et al.
Molecular pharmacology, 62(3), 566-577 (2002-08-16)
Alkyl-substituted benzothiadiazides (BTDs) were tested for their effects on (R,S)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)-type glutamate receptors. In excised patches, the 5'-ethyl derivative "D1" blocked the desensitization of AMPA receptor currents during prolonged application of glutamate (EC(50), 36 microM), and it slowed deactivation
Dean Phillips et al.
Bioorganic & medicinal chemistry, 10(5), 1229-1248 (2002-03-12)
AMPA receptors form a major subdivision of the glutamate receptor family that mediates excitatory synaptic transmission in the brain. Currents through AMPA receptors can be up- or down-regulated by compounds that allosterically modulate receptor kinetics through binding sites distinct from
I Zivkovic et al.
The Journal of pharmacology and experimental therapeutics, 272(1), 300-309 (1995-01-01)
7-Chloro-3-Methyl-3-4-Dihydro-2H-1,2,4 Benzothiadiazine S,S Dioxide (IDRA 21), which attenuates the rapid autodesensitization of DL-alpha-amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (AMPA)-selective glutamate receptors and increases excitatory synaptic strength, improves cognition (learning and memory), as revealed by its ability to improve performance in water maze and passive
Ludise Malkova et al.
Neuropharmacology, 60(7-8), 1262-1268 (2010-12-28)
Nootropic agents or cognitive enhancers are purported to improve mental functions such as cognition, memory, or attention. The aim of our study was to determine the effects of two possible cognitive enhancers, huperzine A and IDRA 21, in normal young
Gabriele Losi et al.
Neuropharmacology, 46(8), 1105-1113 (2004-04-28)
IDRA-21 (7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide) reduces alpha-amino-3-hydroxy-5-methylisoxazolepropionic acid (AMPA) receptors desensitisation in vitro and restores learning and cognitive impairment in vivo. In this study, we show that in cerebellar granule cells (CGCs) in culture IDRA-21 reduces N-methyl-d-aspartate receptor (NMDAR) whole-cell currents. The

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