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MW 389.9 Da, Purity >98%. Positive allosteric modulator of AMPA receptors. Produces a fast inhibition of AMPA receptor desensitization and a much slower potentiation of the AMPA current. Also available in Kit: Ionotropic agonists (ab120323).

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Images

Chemical Structure - Cyclothiazide, AMPA receptor desensitisation inhibitor (AB120061), expandable thumbnail
  • Cellular Activation - Cyclothiazide, AMPA receptor desensitisation inhibitor (AB120061), expandable thumbnail

Publications

Key facts

CAS number
2259-96-3
Purity
> 98%
Form
Solid
Molecular weight
389.9 Da
Molecular formula
C14H16ClN3O4S2
PubChem identifier
2910
Nature
Synthetic

Alternative names

Recommended products

MW 389.9 Da, Purity >98%. Positive allosteric modulator of AMPA receptors. Produces a fast inhibition of AMPA receptor desensitization and a much slower potentiation of the AMPA current. Also available in Kit: Ionotropic agonists (ab120323).

Key facts

Purity
> 98%
PubChem identifier
2910
Solubility

Soluble in ethanol to 25 mM.

Soluble in DMSO to 100 mM.

Biochemical name
Cyclothiazide
Biological description

Positive allosteric modulator of AMPA receptors. Produces a fast inhibition of AMPA receptor desensitization and a much slower potentiation of the AMPA current. Also available in Kit: Ionotropic agonists (ab120323).

Canonical SMILES
C1C2CC(C1C=C2)C3NC4=CC(=C(C=C4S(=O)(=O)N3)S(=O)(=O)N)Cl
InChI
InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)
InChIKey
BOCUKUHCLICSIY-UHFFFAOYSA-N
IUPAC name
3-(2-bicyclo[2.2.1]hept-5-enyl)-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
Store under desiccating conditions, The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

Glutamate Receptor 1 also called AMPA receptor 1 is an ionotropic receptor that mediates fast synaptic transmission in the central nervous system. It is part of a larger family of glutamate receptors including subtypes GluA2 GluA3 and GluA4. The AMPA receptor structure typically forms a tetrameric complex mainly located in neuronal cells such as those in the hippocampus and cerebral cortex. The receptor has a mass of approximately 100 kDa. These receptors enable rapid excitatory signaling by allowing the flow of sodium (Na+) and calcium (Ca2+) ions into the cell upon binding glutamate.

Biological function summary

The AMPA receptors facilitate neuronal communication and plasticity by modulating synaptic strength. This modulation occurs through processes such as potentiation and desensitisation where the receptor's response to glutamate changes. Potentiated sulfonamides like cyclothiazide can influence AMPA receptor activity by preventing desensitization maintaining prolonged neurotransmission. Cyclothiazide itself binds within the AMPA structure altering the conformation to prevent the desensitised state which is key in sustaining synaptic efficacy. AMPA receptors also interact with auxiliary proteins like TARPs (Transmembrane AMPA Receptor Regulatory Proteins) that assist in their trafficking and channel properties.

Pathways

AMPA receptors play a significant role in the glutamatergic pathway integral for synaptic transmission and neuroplasticity. This pathway influences learning and memory processes. AMPA receptors also interact with the NMDA receptors in long-term potentiation (LTP) a process critical for memory formation and synaptic strength. Additionally they connect with proteins like CaMKII (Calcium/Calmodulin-dependent protein kinase II) during signal transduction processes inside neurons important for cellular responses following synaptic activation.

Associated diseases and disorders

Abnormal AMPA receptor function associates with neurodegenerative conditions like Alzheimer’s disease and neurological disorders such as epilepsy. Dysregulation can lead to conditions characterized by excitotoxicity where excessive receptor activity causes neuronal damage. The abnormal interaction between AMPA receptors and proteins like the NMDA receptor may contribute to these conditions. Therapies targeting AMPA receptors aiming to modulate their activity present possible strategies for managing these diseases highlighting their importance on the AMPA receptors market.

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2 product images

  • Chemical Structure - Cyclothiazide, AMPA receptor desensitisation inhibitor (ab120061), expandable thumbnail

    Chemical Structure - Cyclothiazide, AMPA receptor desensitisation inhibitor (ab120061)

    2D chemical structure image of ab120061, Cyclothiazide, AMPA receptor desensitisation inhibitor

  • Cellular Activation - Cyclothiazide, AMPA receptor desensitisation inhibitor (ab120061), expandable thumbnail
    Image from Case DT, et al. Plos One, 6(6), e20756. Fig S4,; doi: 10.1371/journal.pone.0020756

    Cellular Activation - Cyclothiazide, AMPA receptor desensitisation inhibitor (ab120061)

    To determine the capability of VCN-LSO synapses to support repetitive activity in the developing circuit, we added cyclothiazide to the perfusate to prevent AMPAR desensitization and measured responses to 50 Hz pulse-train stimuli delivered to the ventral acoustic stria. A. Representative responses to 50 Hz pulse-trains in P2, P5, and P9 cells; responses to the first five pulses only are shown. Greater paired-pulse depression between pulse 1 and 2 is evident in the youngest cell than in the older cells.

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