77-LH-28-1

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H32N2O
Molecular Weight	328.4916
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC1CCN(CCCN2C(=O)CCC3=CC=CC=C23)CC1

InChI

InChIKey=PHMGZAICAOYEAF-UHFFFAOYSA-N

InChI=1S/C21H32N2O/c1-2-3-7-18-12-16-22(17-13-18)14-6-15-23-20-9-5-4-8-19(20)10-11-21(23)24/h4-5,8-9,18H,2-3,6-7,10-17H2,1H3

HIDE SMILES / InChI

Molecular Formula	C21H32N2O
Molecular Weight	328.4916
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/21964721 | https://www.ncbi.nlm.nih.gov/pubmed/20600173

77-LH-28-1 Oxalate is a salt of 77-LH-28-1. This drug is a potent, selective, bioavailable and brain-penetrant agonist of muscarinic acetylcholine receptor subtype 1. 77-LH-28-1 can increase network oscillations relevant to cognitive processing that would support the potential use of this mechanism in the treatment of cognitive impairment. 77-LH-28-1 exhibited U-shaped dose-effect functions in attenuating cocaine discrimination. 77-LH-28-1, can significantly enhance donepezil-induced gamma oscillations. These data support the notion that it should be possible to find a more efficacious AChE inhibitor or an adjunctive approach, to provide a better therapeutic intervention in Alzheimer's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Agonist 2678	8.1 null [pEC50]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Agonist 2678	5.6 null [pEC50]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Antagonist 2778	5.5 null [pIC50]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Antagonist 2778	5.9 null [pIC50]
Muscarinic acetylcholine receptor M5 62 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Antagonist 2778	5.8 null [pIC50]

Conditions

Condition	Modality	Highest Phase	Product
Cognitive impairment 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18454168	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20600173	Primary	Basic research	Unknown Approved Use Unknown
Cocaine addiction 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21964721	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Characterization of a CNS penetrant, selective M1 muscarinic receptor agonist, 77-LH-28-1.	2008 Jul	18454168
Molecular mechanisms of bitopic ligand engagement with the M1 muscarinic acetylcholine receptor.	2014 Aug 22	25006252
Synthesis and biological evaluation of a novel series of heterobivalent muscarinic ligands based on xanomeline and 1-[3-(4-butylpiperidin-1-yl)propyl]-1,2,3,4-tetrahydroquinolin-2-one (77-LH-28-1).	2014 Nov 13	25275964

Patents

Sample Use Guides

In Vivo Use Guide

3 mg/kg

Route of Administration: Other

In Vitro Use Guide

77-LH-28-1 was assessed for their ability to initiate single-unit cell firing in the CA1 region of the rat hippocampus. 77-LH-28-1 stimulated single-unit firing, acting as a full agonist with respect to carbachol, with a pEC50 value of 6.3.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:11:29 GMT 2023` Edited by `admin` on `Sat Dec 16 17:11:29 GMT 2023`
Record UNII	9ZH28BM589
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

77-LH-28-1

Common Name

English

2(1H)-Quinolinone, 1-[3-(4-butyl-1-piperidinyl)propyl]-3,4-dihydro-

Systematic Name

English

77LH28-1

Common Name

English

1-(3-(4-BUTYLPIPERIDIN-1-YL)PROPYL)-3,4-DIHYDRO-1H-QUINOLIN-2-ONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

10236758