AM-1172

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H39NO2
Molecular Weight	409.6041
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCNC(=O)C1=CC=C(O)C=C1

InChI

InChIKey=XCWBOAHOJHPWLA-DOFZRALJSA-N

InChI=1S/C27H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-28-27(30)25-20-22-26(29)23-21-25/h6-7,9-10,12-13,15-16,20-23,29H,2-5,8,11,14,17-19,24H2,1H3,(H,28,30)/b7-6-,10-9-,13-12-,16-15-

HIDE SMILES / InChI

Molecular Formula	C27H39NO2
Molecular Weight	409.6041
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	4
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cannabinoid receptor 1 30 Target ID: P20272 Gene ID: 25248.0 Gene Symbol: Cnr1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15138300	Partial Agonist 290	86.0 nM [EC50]
Cannabinoid receptor 2 27 Target ID: P34972 Gene ID: 1269.0 Gene Symbol: CNR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15138300	Binding Agent 1064	189.0 nM [IC50]
anandamide transport 1 Target ID: anandamide transport Sources: https://www.ncbi.nlm.nih.gov/pubmed/15138300	Inhibitor 8297	2.5 µM [IC50]
Fatty-acid amide hydrolase 1 2 Target ID: O08914 Gene ID: 14073.0 Gene Symbol: Faah Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17901541	Inhibitor 8297	3.18 µM [IC50]
Cannabinoid receptor 1 30 Target ID: P20272 Gene ID: 25248.0 Gene Symbol: Cnr1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15138300	Partial Agonist 290	271.0 nM [IC50]
Cannabinoid receptor 2 27 Target ID: P34972 Gene ID: 1269.0 Gene Symbol: CNR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15138300	Partial Agonist 290	189.0 nM [IC50]
uptake of arachidonoyl ethanolamide (anandamide, AEA) 1 Target ID: uptake of arachidonoyl ethanolamide (anandamide, AEA) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16461355	Inhibitor 8297

PubMed

Title	Date	PubMed
Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172.	2004 Jun 8	15138300
Anandamide uptake is consistent with rate-limited diffusion and is regulated by the degree of its hydrolysis by fatty acid amide hydrolase.	2006 Apr 7	16461355
Arvanil, olvanil, AM 1172 and LY 2183240 (various cannabinoid CB1 receptor agonists) increase the threshold for maximal electroshock-induced seizures in mice.	2018 Feb	29335158

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:00:31 GMT 2023` Edited by `admin` on `Sat Dec 16 14:00:31 GMT 2023`
Record UNII	G5DZB59PZA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AM-1172

Code

English

N-(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAEN-1-YL-4-HYDROXYBENZAMIDE

Systematic Name

English

BENZAMIDE, N-(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAEN-1-YL-4-HYDROXY-

Systematic Name

English

BENZAMIDE, N-(5Z,8Z,11Z,14Z)-5,8,11,14-EICOSATETRAENYL-4-HYDROXY-

Systematic Name

English

Code System Code Type Description

PUBCHEM

10364179