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Merck
CN

A6478

(R,S)-AM1241

≥98% (HPLC), solid

Synonym(s):

(R,S)-3-(2-Iodo-5-nitrobenzoyl)-1-(1-methyl-2-piperidinylmethyl)-1H-indole

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About This Item

Empirical Formula (Hill Notation):
C22H22IN3O3
CAS Number:
444912-48-5
Molecular Weight:
503.33
NACRES:
NA.77
PubChem Substance ID:
24891092
UNSPSC Code:
12352200
MDL number:
MFCD11045986
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Quality Level

100

assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

yellow

solubility

DMSO: ~18 mg/mL at 60 °C

SMILES string

CN1CCCCC1Cn2cc(C(=O)c3cc(ccc3I)[N+]([O-])=O)c4ccccc24

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

InChI key

ZUHIXXCLLBMBDW-UHFFFAOYSA-N

Application

(R,S)-AM1241 has been used as a cannabinoid CB2 agonist:
  • to study its inhibitory effect on bone cancer-induced pain and bone loss
  • to study the effect of its interaction with 17βestradiol on proliferation activity in primary human osteoblasts
  • to evaluate the sites of CB2 mediated antinociception in vivo.

Biochem/physiol Actions

AM1241 acts as an antinociceptive agent in several animal pain models. It has a potential to delay disease progression in amyotrophic lateral sclerosis (ALS) mouse model. Intrathecal, intravenous or intraperitoneal administration of AM1241 reduces hyperalgesia and allodynia in neuropathic rats.
Selective CB2 cannabinoid receptor agonist

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
108K4602V
0000044412
0000044442
0000022688
108K4602

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The cannabinoid CB2 receptor-specific agonist AM1241 increases pentylenetetrazole-induced seizure severity in Wistar rats
de Carvalho CR, et al.
Epilepsy Research, 127(2), 160-167 (2016)
AM1241, a cannabinoid CB2 receptor selective compound, delays disease progression in a mouse model of amyotrophic lateral sclerosis
Kim K, et al.
European Journal of Pharmacology, 542(1-3), 100-105 (2006)
A synergistic interaction of 17-$\beta$-estradiol with specific cannabinoid receptor type 2 antagonist/inverse agonist on proliferation activity in primary human osteoblasts
Hojnik M, et al.
Biomedical Reports, 3(4), 554-558 (2015)
Elizabeth J Rahn et al.
Pharmacology, biochemistry, and behavior, 98(4), 493-502 (2011-03-09)
Cannabinoid CB(2) agonists produce antinociception without central nervous system (CNS) side-effects. This study was designed to characterize the pharmacological and antinociceptive profile of AM1710, a CB(2) agonist from the cannabilactone class of cannabinoids. AM1710 did not exhibit off-target activity at
Elizabeth J Rahn et al.
The AAPS journal, 12(2), 147-157 (2010-02-04)
Cannabinoid CB(2) receptors represent a therapeutic target that circumvents unwanted central side effects (e.g., psychoactivity and/or addiction) associated with activation of CB(1) receptors. One of the primary investigative tools used to study functions of the CB(2) receptor is the aminoalkylindole
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Global Trade Item Number

SKUGTIN
A6478-5MG04061832555416
A6478-25MG04061832555409

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