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Merck
CN

SML3125

LEI-401

≥98% (HPLC)

Synonym(s):

N-(Cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide, N-(Cyclopropylmethyl)-6-[(3S)-3-hydroxy-1-pyrrolidinyl]-2-[(3S)-3-phenyl-1-piperidinyl]-4-pyrimidinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C24H31N5O2
CAS Number:
Molecular Weight:
421.54
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
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InChI

1S/C24H31N5O2/c30-20-10-12-28(16-20)22-13-21(23(31)25-14-17-8-9-17)26-24(27-22)29-11-4-7-19(15-29)18-5-2-1-3-6-18/h1-3,5-6,13,17,19-20,30H,4,7-12,14-16H2,(H,25,31)/t19-,20+/m1/s1

InChI key

GFHJYPQZBBHOCC-UXHICEINSA-N

SMILES string

O=C(C1=CC(N2CC[C@@H](C2)O)=NC(N3CCC[C@H](C3)C4=CC=CC=C4)=N1)NCC5CC5

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

Biochem/physiol Actions

CNS-active, potent and selective inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD)
LEI-401 is a CNS-active, potent and selective inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD). LEI-401 reduces N-acylethanolamines (NAEs) in in the brain of freely moving mice and neuroblastoma cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Elliot D Mock et al.
Journal of medicinal chemistry, 64(1), 481-515 (2021-01-01)
N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs
Elliot D Mock et al.
Nature chemical biology, 16(6), 667-675 (2020-05-13)
N-acylethanolamines (NAEs), which include the endocannabinoid anandamide, represent an important family of signaling lipids in the brain. The lack of chemical probes that modulate NAE biosynthesis in living systems hamper the understanding of the biological role of these lipids. Using

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