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CasNo: 22503-72-6
Molecular Formula: C8H9 Cl N2 O2 S
Chemical Properties |
white to off-white crystalline powder IDRA-21 is a benzothiadiazine derivative and a chiral molecule. |
Description | IDRA-21 is a synthetic compound recognized as a positive allosteric modulator of the AMPA receptor, a crucial component in excitatory synaptic transmission. By inhibiting AMPA receptor desensitization, IDRA-21 enhances excitatory synaptic strength, potentially leading to improved cognitive function. |
Uses |
In animal studies, IDRA-21 has demonstrated notable nootropic effects, significantly enhancing learning and memory abilities. It exhibits potent activity, being approximately 10–30 times more effective than aniracetam in reversing cognitive deficits induced by certain compounds. Moreover, its effects can last up to 48 hours after a single dose. These cognitive benefits are attributed to the compound's ability to promote the induction of long-term potentiation between synapses in the brain. While IDRA-21 generally appears safe in normal conditions without causing neurotoxicity, caution is warranted in situations of neuronal damage such as stroke or seizures, where it may exacerbate existing injuries. |
Biological Activity |
Inhibits AMPA receptor desensitization and enhances cognition by a related mechanism. More able to cross the blood-brain barrier than cyclothiazide (6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiazidiazine-7-sulfonamide-1,1-dioxide ). |
InChI:InChI=1/C8H9ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-5,10-11H,1H3
IDRA 21 doubled the charge transfer at a concentration of 70 μM, suggesting that this compound can facilitate excitatory neurotransmission via GluR 1/2 receptors. We next sought to exploit this mechanism of action by examining the drug as a potential cognition-enhancing agent in non-human primates.
In this retention trial, the IDRA 21-treated rats performed considerably better than those that received the vehicle. Moreover, oral IDRA 21 (ED50 = 7.6 microM) attenuated the performance impairment induced by the AMPA receptor antagonist 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo (F) quinoxaline in the water maze test.
2-amino-5-chlorobenzenesulfonamide
acetaldehyde
IDRA 21
Conditions | Yield |
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In acetonitrile;
|
|
With camphorsulfonic acid; In acetonitrile; at 20 ℃; Sealed tube;
|
2-amino-5-chlorobenzenesulfonamide
ethanol
IDRA 21
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; at 110 ℃; for 12h;
|
80% |
2-amino-5-chlorobenzenesulfonamide
acetaldehyde
4-Chlor-2-acetylsulfamoyl-acetanilid
2-acetylamino-benzenesulfonic acid acetylamide
2-amino-5-chloro-N-ethylbenzenesulfonamide
5-chloro-2-(ethylamino)benzenesulfonamide
N-acetyl-5-chloro-2-nitrobenzenesulfonamide