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SML2646

Sigma-Aldrich

CX614

≥98% (HPLC)

Synonym(s):

2,3,6a,7,8,9-Hexahydro-11H-1,4-dioxino[2,3-g]pyrrolo[2,1-b][1,3]benzoxazin-11-one, 2H,3H,6aH-Pyrrolidino[2",1"-3′,2′]1,3-oxazino[6′,5′-5,4]benzo[e]1,4-dioxan-10-one, BDP 37, BDP-37, CX 614, CX-614, LiD 37

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About This Item

Empirical Formula (Hill Notation):
C13H13NO4
CAS Number:
191744-13-5
Molecular Weight:
247.25
MDL number:
MFCD13248581
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C13H13NO4/c15-13-8-6-10-11(17-5-4-16-10)7-9(8)18-12-2-1-3-14(12)13/h6-7,12H,1-5H2

InChI key

RQEPVMAYUINZRE-UHFFFAOYSA-N

Biochem/physiol Actions

CX614 (BDP-37) is a brain-penetrant class I ampakine (benzoxazine subgroup of benzamide-type) with AMPA receptor (AMPAR; iGluR) positive allosteric modulator (PAM) activity via targeting a binding site shared by cyclothiazide (CTZ), but distinct from that of GYKI 52466. CX614 enhances field excitatory postsynaptic potentials (amplitude & duration) in rat hippocampal slices and autaptically evoked excitatory postsynaptic currents in neuronal cultures (EC50 of 20-40 μM) by blocking desensitization and slowing deactivation of responses to glutamate. CX614 is also widely employed for studying AMPAR-mediated physiological responses in vivo (1-10 mg/kg n rats and mice via i.p.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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U S Hess et al.
Neuroscience, 121(2), 509-521 (2003-10-03)
It has been proposed that glutamatergic and dopaminergic systems are functionally opposed in their regulation of striatal output. The present study tested the effects of drugs that enhance AMPA-receptor-mediated glutamatergic transmission (ampakines) for their effects on dopamine-related alterations in cortical
Daniel P Radin et al.
Biochemical pharmacology, 148, 308-314 (2018-01-14)
It was previously reported that Stargazin (STG) enhances the surface expression of AMPA receptors, controls receptor gating and slows channel desensitization as an auxiliary subunit of the receptors. Ampakines are a class of AMPA receptor positive allosteric modulators that modify
Daniel P Radin et al.
Anticancer research, 38(6), 3461-3465 (2018-06-01)
Mounting evidence suggests that trophic cell signaling can be mediated by alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) activation. It has been demonstrated that exogenous application of brain-derived neurotrophic factor (BDNF) is highly neuroprotective in vitro against neurotoxic insults such as standard chemotherapies.
Daniel P Radin et al.
Anticancer research, 38(1), 265-269 (2017-12-27)
The 5-year survival rate of glioblastoma (GBM) is ~10%, demonstrating that a new therapeutic modality for this cancer is desperately needed. Complicating the search for such a modality is that most large molecules cannot pass through the blood brain barrier
L Cavalleri et al.
Molecular psychiatry, 23(4), 812-823 (2017-11-22)
Among neurobiological mechanisms underlying antidepressant properties of ketamine, structural remodeling of prefrontal and hippocampal neurons has been proposed as critical. The suggested mechanism involves downstream activation of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors, which trigger mammalian target of rapamycin (mTOR)-dependent structural plasticity
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