M182

MDL-12,330A hydrochloride

Name: MDL-12,330A hydrochloride
Brand: SIGMA

≥98% (HPLC), Adenylyl cyclase inhibitor, powder

Synonym(s):

cis-N-(2-Phenylcyclopentyl)-azacyclotridec-1-en-2-amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₆N₂ · HCl

CAS Number:

40297-09-4

Molecular Weight:

377.01

UNSPSC Code:

41106305

PubChem Substance ID:

24896696

NACRES:

NA.77

MDL number:

MFCD00210204

Product Name

MDL-12,330A hydrochloride, ≥98% (HPLC), powder

SMILES string

Cl[H].C1CCCCCN=C(CCCCC1)N[C@H]2CCC[C@H]2c3ccccc3

InChI

1S/C23H36N2.ClH/c1-2-4-6-11-18-23(24-19-12-7-5-3-1)25-22-17-13-16-21(22)20-14-9-8-10-15-20;/h8-10,14-15,21-22H,1-7,11-13,16-19H2,(H,24,25);1H/t21-,22-;/m0./s1

InChI key

CKOPQUCSDBVAQG-VROPFNGYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

Bioactive Small Molecules

Application

MDL-12,330A hydrochloride has been used as an inhibitor of adenylyl cyclase to block cyclic AMP signaling in mesenchymal stem/stromal cells (MSC). It has also been used as an adenylyl cyclase blocker to test its effect on the locomotor activity based on tail suspension test (TST) in mice.

Biochem/physiol Actions

Adenylyl cyclase inhibitor.

MDL-12,330A is a cycloalkyl lactamimide that acts as a voltage-gated potassium channel blocker (KV) leading to extension of action potential duration (APD) and favoring insulin secretion. It also blocks calcium (Ca²⁺) entry.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Bile acid stimulates hepatocyte polarization through a cAMP-Epac-MEK-LKB1-AMPK pathway.

Dong Fu et al.

Proceedings of the National Academy of Sciences of the United States of America, 108(4), 1403-1408 (2011-01-12)

This study describes a unique function of taurocholate in bile canalicular formation involving signaling through a cAMP-Epac-MEK-Rap1-LKB1-AMPK pathway. In rat hepatocyte sandwich cultures, polarization was manifested by sequential progression of bile canaliculi from small structures to a fully branched network.

The adenylyl cyclase inhibitor MDL-12,330A potentiates insulin secretion via blockade of voltage-dependent K(+) channels in pancreatic beta cells.

Xiaodong Li et al.

PloS one, 8(10), e77934-e77934 (2013-11-10)

Adenylyl cyclases (ACs) play important role in regulating pancreatic beta cell growth, survival and secretion through the synthesis of cyclic AMP (cAMP). MDL-12,330A and SQ 22536 are two AC inhibitors used widely to establish the role of ACs. The goal

Mesenchymal stem cell mechanotransduction is cAMP dependent and regulated by adenylyl cyclase 6 and the primary cilium.

Gillian P Johnson et al.

Journal of cell science, 131(21) (2018-10-12)

Mechanical loading is a potent stimulus of bone adaptation, requiring the replenishment of the osteoblast from a progenitor population. One such progenitor is the mesenchymal stem cell (MSC), which undergoes osteogenic differentiation in response to oscillatory fluid shear. Yet, the

Gαq protein signaling in the bed nucleus of the stria terminalis regulate the lipopolysaccharide-induced despair-like behavior in mice.

Nao Fukuwada et al.

AIMS neuroscience, 7(4), 438-458 (2020-12-03)

Major depressive disorder (MDD) is highly comorbid with anxiety disorders. It has been reported that the bed nucleus of the stria terminalis (BNST) is important for the induction of anxiety and MDD. Recently, the Gαq protein signaling within the BNST

Effects of scoparone on dopamine release in PC12 cells.

Yoo Jung Yang et al.

Fitoterapia, 81(6), 497-502 (2010-01-19)

The effects of scoparone on dopamine release in PC12 cells were investigated. Scoparone at 50-200 microM increased dopamine release into the culture medium. However, the released levels of dopamine by scoparone were not altered in the absence of extracellular Ca(2+)

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