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A6478

(R,S)-AM1241

Name: (R,S)-AM1241
Brand: SIGMA

≥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

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Properties

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

Description

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

Selective CB₂ cannabinoid receptor agonist

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.

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H315,H319,H334,H335

pcodes

P302 + P352 - P305 + P351 + P338

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

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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)

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)

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)

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