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SML1861

Sigma-Aldrich

J104129 fumarate

≥98% (HPLC)

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Synonym(s):
(αR)-α-Cyclopentyl-α-hydroxy-N-[1-(4-methyl-3-penten-1-yl)-4-piperidinyl]-Benzeneacetamide fumarate, J-104129
Empirical Formula (Hill Notation):
C24H36N2O2 · C4H4O4
CAS Number:
257603-40-0
Molecular Weight:
500.63
MDL number:
MFCD09753272
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -6 to -8°, c = 1 in methanol

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(O)/C=C/C(O)=O.CC(C)=CCCN(CC1)CCC1NC([C@](C2CCCC2)(O)C3=CC=CC=C3)=O

InChI

1S/C24H36N2O2.C4H4O4/c1-19(2)9-8-16-26-17-14-22(15-18-26)25-23(27)24(28,21-12-6-7-13-21)20-10-4-3-5-11-20;5-3(6)1-2-4(7)8/h3-5,9-11,21-22,28H,6-8,12-18H2,1-2H3,(H,25,27);1-2H,(H,5,6)(H,7,8)/b;2-1+/t24-;/m0./s1

InChI key

HUCQUCITPHOUAC-DSSYAJFBSA-N

Biochem/physiol Actions

J104129 is a muscarinic M3 receptor antagonist greater than 100-fold selectivity for M3 over M2 receptors. Its Ki for M3 receptors = 4.2 nM compared to a Ki of 490 nM for M2 receptors. J-104129 showed potent bronchodilator activity in animal studies.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Aline Fassini et al.
Journal of neuroscience research, 93(5), 830-838 (2015-01-17)
The prelimbic cortex (PL), a limbic structure, sends projections to areas involved in the control of cardiovascular responses. Stimulation of the PL with acetylcholine (ACh) evokes depressor and tachycardiac responses mediated by local PL muscarinic receptors. Early studies demonstrated that
M Mitsuya et al.
Bioorganic & medicinal chemistry, 7(11), 2555-2567 (2000-01-13)
A new class of 4-acetamidopiperidine derivatives has been synthesized and investigated for human muscarinic receptor subtype selectivity. Introduction of a hydrocarbon chain of appropriate length into the piperidine nitrogen of the racemic N-(piperidin-4-yl)-2-cyclobutyl-2-hydroxy-2-phenylacetamide platform conferred up to 70-fold selectivity for
Yun Zhu et al.
Journal of neurochemistry, 137(2), 226-239 (2016-01-30)
Neurons in the vestibular nuclei have a vital function in balance maintenance, gaze stabilization, and posture. Although muscarinic acetylcholine receptors (mAChRs) are expressed and involved in regulating vestibular function, it remains unclear how individual mAChR subtypes regulate vestibular neuronal activity.

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