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Details

Stereochemistry RACEMIC
Molecular Formula C22H22IN3O3
Molecular Weight 503.3337
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AM-1241

SMILES

CN1CCCCC1Cn2cc(c3ccccc32)C(=O)c4cc(ccc4I)N(=O)=O

InChI

InChIKey=ZUHIXXCLLBMBDW-UHFFFAOYSA-N
InChI=1S/C22H22IN3O3/c1-24-11-5-4-6-16(24)13-25-14-19(17-7-2-3-8-21(17)25)22(27)18-12-15(26(28)29)9-10-20(18)23/h2-3,7-10,12,14,16H,4-6,11,13H2,1H3

HIDE SMILES / InChI

Molecular Formula C22H22IN3O3
Molecular Weight 503.3337
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21610490

AM-1241, was developed at the University of Connecticut. AM-1241 was derived from the known non-selective indole class of cannabinoid receptor agonists represented by WIN55212-2 and JWH-015. Compared to earlier agonists that exhibited modest selectivities, AM-1241 exhibited 82-fold selectivity for CB2 over CB1 based on binding affinity assays. Using AM-1241, it was demonstrated that a selective CB2 receptor agonist provides relief of pain without the psychotropic effects produced by a pan-cannabinoid receptor agonist. After injection of AM-1241 into the hindpaw of a mouse, analgesic activity toward a thermal stimulus applied to the same paw was observed. Co-administration of a CB2 receptor antagonist blocked the effect, while a CB1 antagonist did not. The results of this initial study led researchers to investigate the use of a CB2 receptor selective agonist for the treatment of pain as well as other disease states that involve the CB2 receptor. It was found that AM-1241 inhibited nociception in CB+/+ mice, but not CB2+/+ littermates, providing strong evidence of its direct activation of CB2. AM-1241 was shown to dose-dependently inhibit capsaicin-induced release of the pain biomarker calcitonin gene-related peptide (CGRP) in rat spinal cord slices, a result that also suggests the presence of CB2 in neurons of the spinal cord. AM-1241 has being shown to be a promising target for the management of cancer pain.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro pharmacological characterization of AM1241: a protean agonist at the cannabinoid CB2 receptor?
2006 Sep
Effect of cannabinoid receptor agonists on streptozotocin-induced hyperalgesia in diabetic neuropathy.
2008
Cannabinoids desensitize capsaicin and mustard oil responses in sensory neurons via TRPA1 activation.
2008 Jan 30
Selective activation of cannabinoid CB2 receptors suppresses neuropathic nociception induced by treatment with the chemotherapeutic agent paclitaxel in rats.
2008 Nov
Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging.
2009 Jan
Discovery and optimization of 1-(4-(pyridin-2-yl)benzyl)imidazolidine-2,4-dione derivatives as a novel class of selective cannabinoid CB2 receptor agonists.
2011 Oct 27
Patents

Patents

Sample Use Guides

Rats: 1, 3 and 10 mg/kg IP
Route of Administration: Intraperitoneal
In Vitro Use Guide
Curator's Comment:: AM-1241 pretreatment attenuates microglial activation by shifting M1 to M2 activated state via CB2 receptor
Pretreatment with 5 uM AM-1241 at 1 h before N9 murine microglia were exposed to LPS plus IFNγ decreased the expression of inducible nitric oxide synthase (iNOS) and the release of pro-inflammatory factors, increased the expression of arginase 1 (Arg-1) and the release of anti-inflammatory and neurotrophic factors in microglia
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:29:26 UTC 2021
Edited
by admin
on Fri Jun 25 22:29:26 UTC 2021
Record UNII
DLM851L3RD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AM-1241
Common Name English
1-((N-METHYL-2-PIPERIDINYL)METHYL)-3-(2-IODO-5-NITROBENZOYL)-1H-INDOLE
Systematic Name English
METHANONE, (2-IODO-5-NITROPHENYL)(1-((1-METHYL-2-PIPERIDINYL)METHYL)-1H-INDOL-3-YL)-
Systematic Name English
J1.955.911D
Code English
Code System Code Type Description
FDA UNII
DLM851L3RD
Created by admin on Fri Jun 25 22:29:26 UTC 2021 , Edited by admin on Fri Jun 25 22:29:26 UTC 2021
PRIMARY
PUBCHEM
10141893
Created by admin on Fri Jun 25 22:29:26 UTC 2021 , Edited by admin on Fri Jun 25 22:29:26 UTC 2021
PRIMARY
CAS
444912-48-5
Created by admin on Fri Jun 25 22:29:26 UTC 2021 , Edited by admin on Fri Jun 25 22:29:26 UTC 2021
PRIMARY
WIKIPEDIA
AM-1241
Created by admin on Fri Jun 25 22:29:26 UTC 2021 , Edited by admin on Fri Jun 25 22:29:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
binding assay
Ki
Related Record Type Details
ACTIVE MOIETY