MEPPEP

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H25F3N2O2
Molecular Weight	454.4841
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC=C1)[C@H]2C[C@@H](N[C@H](C)C3=CC=CC=C3)C(=O)N2C4=CC=C(C=C4)C(F)(F)F

InChI

InChIKey=BPTDWRQYMMIHHK-UOKFIYJESA-N

InChI=1S/C26H25F3N2O2/c1-17(18-7-4-3-5-8-18)30-23-16-24(19-9-6-10-22(15-19)33-2)31(25(23)32)21-13-11-20(12-14-21)26(27,28)29/h3-15,17,23-24,30H,16H2,1-2H3/t17-,23-,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C26H25F3N2O2
Molecular Weight	454.4841
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20851117 | https://www.ncbi.nlm.nih.gov/pubmed/31268519 | https://www.ncbi.nlm.nih.gov/pubmed/17392732 | https://www.ncbi.nlm.nih.gov/pubmed/19573609 | https://clinicaltrials.gov/ct2/show/NCT00598390 | https://clinicaltrials.gov/ct2/show/NCT00816439

MePPEP ((3R,5R)-5-(3-methoxy-phenyl)-3-((R)-1-phenyl-ethylamino)-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one) is an inverse agonist at cannabinoid CB1 receptors. Radiolabeled MePPEP may be used for PET imaging of cannabinoid CB1 receptors in the brain of patients with psychiatric disorders such as alcohol dependence and psychoses.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20851117 \| https://www.ncbi.nlm.nih.gov/pubmed/22910406	Inverse Agonist 80		0.16 nM [Kd]

PubMed

Title	Date	PubMed
The PET radioligand [11C]MePPEP binds reversibly and with high specific signal to cannabinoid CB1 receptors in nonhuman primate brain.	2008 Jan	17392732
Pharmacological characterization of the cannabinoid CB₁ receptor PET ligand ortholog, [³H]MePPEP.	2010 Dec 15	20851117

Sample Use Guides

In Vivo Use Guide

brain positron emission tomography was performed in healthy subjects after injection of ~600 MBq (~80 GBq/µmol) [11C]MePPEP

Route of Administration: Parenteral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:41:10 GMT 2023` Edited by `admin` on `Fri Dec 15 19:41:10 GMT 2023`
Record UNII	5JL4MD0N76
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEPPEP

Common Name

English

(3R,5R)-5-(3-METHOXY-PHENYL)-3-((R)-1-PHENYL-ETHYLAMINO)-1-(4-TRIFLUOROMETHYL-PHENYL)-PYRROLIDIN-2-ONE

Systematic Name

English

2-PYRROLIDINONE, 5-(3-METHOXYPHENYL)-3-(((1R)-1-PHENYLETHYL)AMINO)-1-(4-(TRIFLUOROMETHYL)PHENYL)-, (3R,5R)-

Systematic Name

English

Code System Code Type Description

CAS

1059188-74-7

Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023

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PUBCHEM

25107855

Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023

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FDA UNII

5JL4MD0N76

Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023

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EPA CompTox

DTXSID50147419

Created by admin on Fri Dec 15 19:41:10 GMT 2023 , Edited by admin on Fri Dec 15 19:41:10 GMT 2023

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Related Record Type Details


					CS3P21MZK4

MEPPEP C-11

LABELED -> NON-LABELED

Amount: