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C9847

Cyclothiazide

AMPA glutamate receptor blocker, powder

Synonym(s):

6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2-4-benzothiadiazine-7-sulfonamide 1,1-dioxide

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$136.00

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$322.00

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About This Item

Empirical Formula (Hill Notation):
C14H16ClN3O4S2
CAS Number:
2259-96-3
Molecular Weight:
389.88
NACRES:
NA.77
PubChem Substance ID:
24278350
UNSPSC Code:
12352125
EC Number:
218-859-7
MDL number:
MFCD00210192
Form:
powder
Quality level:
200

Key Documents

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Product Name

Cyclothiazide,

InChI key

BOCUKUHCLICSIY-QJWLJZLASA-N

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)/t7-,8+,9?,14?/m0/s1

SMILES string

[H][C@@]12CC(C3Nc4cc(Cl)c(cc4S(=O)(=O)N3)S(N)(=O)=O)[C@@]([H])(C1)C=C2

form

powder

originator

Eli Lilly

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... CA1(759), CA4(762), GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)
rat ... Gria1(50592)

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1 of 4

This Item
D9035C4911SML2047
Cyclothiazide

Sigma-Aldrich

C9847

Cyclothiazide

Diazoxide

Sigma-Aldrich

D9035

Diazoxide

Chlorothiazide thiazide diuretic

Sigma-Aldrich

C4911

Chlorothiazide

BPAM344 ≥98% (HPLC)

Sigma-Aldrich

SML2047

BPAM344

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

originator

Eli Lilly

originator

Schering Plough

originator

-

originator

-

Gene Information

human ... CA1(759), CA4(762), GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)
rat ... Gria1(50592)

Gene Information

human ... KCNA1(3736), KCNJ11(3767), KCNJ8(3764), KCNMA1(3778)
mouse ... Kcnj1(56379), Kcnj11(16514)
rat ... Gria1(50592), Kcna1(24520), Kcnj1(24521), Kcnj11(83535), Kcnj8(25472)

Gene Information

human ... CA1(759), CA4(762), SLC12A3(6559)

Gene Information

-

General description

Cyclothiazide is a benzothiadiazine, which has a similar structure to diazoxide.[1]

Application

Cyclothiazide has been used as a α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) desensitization blocker to study the effects of γ2 on receptor desensitization.[2]

Biochem/physiol Actions

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

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 Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000516144
0000516144
0000303633
0000303633
0000254868

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H Schmidhammer et al.
Journal of medicinal chemistry, 32(2), 418-421 (1989-02-01)
(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation
Autumn M Weeks et al.
Neuropharmacology, 85, 57-66 (2014-06-01)
Positive allosteric modulators of α-amino-3-hydroxy-5-methyl-isoxazole-propionic acid (AMPA) ionotropic glutamate receptors facilitate synaptic plasticity and contribute essentially to learning and memory, properties which make AMPA receptors targets for drug discovery and development. One region at which several different classes of positive
Cole W Graydon et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(24), 8358-8372 (2014-06-13)
Sensory processing in the auditory system requires that synapses, neurons, and circuits encode information with particularly high temporal and spectral precision. In the amphibian papillia, sound frequencies up to 1 kHz are encoded along a tonotopic array of hair cells
Lisa Grant et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(12), 4210-4220 (2010-03-26)
Cochlear inner hair cells (IHCs) convert sounds into receptor potentials and via their ribbon synapses into firing rates in auditory nerve fibers. Multivesicular release at individual IHC ribbon synapses activates AMPA-mediated EPSCs with widely ranging amplitudes. The underlying mechanisms and
Martin Loynaz Prieto et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(12), 4449-4459 (2010-03-26)
AMPA receptors are ligand-gated ion channels that show multiple conductance levels, indicating that gating of individual AMPA subunits is to some extent independent of the other subunits. To study AMPAR subunit interactions during activation gating, we recorded from single channels
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