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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

MDL number:

MFCD11045986

UNSPSC Code:

12352200

PubChem Substance ID:

24891092

NACRES:

NA.77

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

GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H334,H335

Precautionary Statements

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pharmacological characterization of AM1710, a putative cannabinoid CB2 agonist from the cannabilactone class: antinociception without central nervous system side-effects.

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

Selective activation of cannabinoid CB(2) receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation.

A G Nackley et al.

Neuroscience, 119(3), 747-757 (2003-06-18)

Activation of cannabinoid CB(2) receptors attenuates thermal nociception in untreated animals while failing to produce centrally mediated effects such as hypothermia and catalepsy [Pain 93 (2001) 239]. The present study was conducted to test the hypothesis that activation of CB(2)

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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