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 33 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 85		0.16 nM [Kd]

PubMed

Title	Date	PubMed
Pharmacological characterization of the cannabinoid CB₁ receptor PET ligand ortholog, [³H]MePPEP.	2010-12-15	20851117
The PET radioligand [11C]MePPEP binds reversibly and with high specific signal to cannabinoid CB1 receptors in nonhuman primate brain.	2008-01	17392732

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 `Mon Mar 31 19:53:26 GMT 2025` Edited by `admin` on `Mon Mar 31 19:53:26 GMT 2025`
Record UNII	5JL4MD0N76
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

MEPPEP

Common 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 Mon Mar 31 19:53:26 GMT 2025 , Edited by admin on Mon Mar 31 19:53:26 GMT 2025

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PUBCHEM

25107855

Created by admin on Mon Mar 31 19:53:26 GMT 2025 , Edited by admin on Mon Mar 31 19:53:26 GMT 2025

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FDA UNII

5JL4MD0N76

Created by admin on Mon Mar 31 19:53:26 GMT 2025 , Edited by admin on Mon Mar 31 19:53:26 GMT 2025

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EPA CompTox

DTXSID50147419

Created by admin on Mon Mar 31 19:53:26 GMT 2025 , Edited by admin on Mon Mar 31 19:53:26 GMT 2025

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Related Record Type Details


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MEPPEP C-11

LABELED -> NON-LABELED

Amount: