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M182

Sigma-Aldrich

MDL-12,330A hydrochloride

≥98% (HPLC), 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
MDL number:
MFCD00210204
UNSPSC Code:
41106305
PubChem Substance ID:
24896696
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

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

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

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.
Adenylyl cyclase inhibitor.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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.
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
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
Kohei Ueno et al.
The European journal of neuroscience, 28(10), 1956-1966 (2008-12-03)
In gustatory receptor neurons (GRNs) in Drosophila melanogaster, Gr5a and one of the Gr64s encode sugar receptors with seven transmembrane domains. Previously, we have shown that the responses to various sugars are depressed in DGsalpha mutant flies (Ueno et al.
Layla Al-Nakkash
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 30(1), 137-150 (2012-07-05)
Daily subcutaneous injections with the phytoestrogen genistein, 600 mg/ kg genistein/day (600G) significantly increased intestinal chloride (Cl(-)) secretion (I(sc), µA/cm(2)) in C57BL/6J female and male murine jejunum after 1-2-weeks treatment. In 600G females, basolateral application of the adenylate cyclase inhibitor
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