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Merck
CN

SML2728

ML375

≥98% (HPLC)

Synonym(s):

(S)-9b-(4-Chlorophenyl)-1-(3,4-difluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one, (S)-9b-(4-Chlorophenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-one, ML 375, VU0483253

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About This Item

Empirical Formula (Hill Notation):
C23H15ClF2N2O2
CAS Number:
1488362-55-5
Molecular Weight:
424.83
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD28411378

Key Documents

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SMILES string

Fc1c(ccc(c1)C(=O)N2[C@]4(N(CC2)C(=O)c5c4cccc5)c3ccc(cc3)Cl)F

InChI key

GXBAKXRLQAPKEE-QHCPKHFHSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -150 to -175, c = 0.5 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

ML375 is an orally active, brain-penetrant, potent and M5 subtype-selective muscarinic acetylcholine receptor (mAChR) negative allosteric modulator (NAM) (IC50 = 300/790 nM against 10 μM NMS-induced Ca2+ mobilization in h/r M5-transfected CHO cells; h/r M1-M4 IC50 >30 μM) that reduces N-methylscopolamine (NMS) ML5 dissociation rate without competing against NMS for receptor binding. M375 shows in vivo efficacy in rat models of substances addiction (cocaine, ethanol, oxycodone) with excellent multispecies pharmacokinetic properties.
Orally active, brain-penetrant, potent & M5-selective muscarinic acetylcholine receptor (mAChR) NAM with in vivo efficacy in rat models of substances addiction.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000529401
0000529401
0000334080
0000334080
0000096680

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Patrick R Gentry et al.
Journal of medicinal chemistry, 56(22), 9351-9355 (2013-10-30)
A functional high throughput screen and subsequent multidimensional, iterative parallel synthesis effort identified the first muscarinic acetylcholine receptor (mAChR) negative allosteric modulator (NAM) selective for the M5 subtype. ML375 is a highly selective M5 NAM with submicromolar potency (human M5
Robert W Gould et al.
ACS chemical neuroscience, 10(8), 3740-3750 (2019-07-04)
Opioid use disorder (OUD) is a debilitating neuropsychiatric condition characterized by compulsive opioid use, dependence, and repeated relapse after periods of abstinence. Given the high risk of developing OUD following prescription opioid use, the continued need for opioid-induced analgesia, and
Alice E Berizzi et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 43(7), 1510-1517 (2018-02-28)
Despite the cost to both individual and society, alcohol use disorders (AUDs) remain a major health risk within society, and both relapse and heavy drinking are still poorly controlled with current medications. Here we demonstrate for the first time that
Barak W Gunter et al.
Addiction biology, 23(5), 1106-1116 (2017-10-19)
Cocaine use disorder (CUD) remains a debilitating health problem in the United States for which there are no Food and Drug Administration-approved treatment options. Accumulating anatomical and electrophysiological evidence indicates that the muscarinic acetylcholine receptor (mAChR) subtype 5 (M5 )
Alice E Berizzi et al.
Molecular pharmacology, 90(4), 427-436 (2016-07-28)
Recently, the first subtype-selective allosteric modulators of the M5 muscarinic acetylcholine receptor (mAChR) have been described, but their molecular mechanisms of action remain unknown. Using radioligand-binding and functional assays of inositol phosphate (IP) accumulation and Ca(2+) mobilization in a recombinant

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