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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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000233404
0000233404
0000189924
0000140518
0000189924

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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.
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
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
Peiyu Xie et al.
International immunopharmacology, 12(1), 158-168 (2011-12-14)
A recombinant complement anaphylatoxin, C4a, inhibited chemotaxis, respiratory burst and histamine release in mast cell-like HMC-1 cells that were treated with recombinant C5a anaphylatoxin. C4a also inhibited histamine release from HMC-1 cells that were induced by recombinant C3a. The inhibition
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.
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