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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All Photos(1)

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

Product Name

(R,S)-AM1241, ≥98% (HPLC), solid

InChI key

ZUHIXXCLLBMBDW-UHFFFAOYSA-N

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

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

Quality Level

100

Related Categories

Bioactive Small Molecule Agonists

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

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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Self-medication of a cannabinoid CB2 agonist in an animal model of neuropathic pain.

Tannia Gutierrez et al.

Pain, 152(9), 1976-1987 (2011-05-10)

Drug self-administration methods were used to test the hypothesis that rats would self-medicate with a cannabinoid CB(2) agonist to attenuate a neuropathic pain state. Self-medication of the CB(2) agonist (R,S)-AM1241, but not vehicle, attenuated mechanical hypersensitivity produced by spared nerve

Immunofluorescent spectral analysis reveals the intrathecal cannabinoid agonist, AM1241, produces spinal anti-inflammatory cytokine responses in neuropathic rats exhibiting relief from allodynia

Wilkerson JL, et al.

Brain and Behavior, 2(2), 155-177 (2012)

Interaction of a Cannabinoid-2 Agonist With Tramadol on Nociceptive Thresholds and Immune Responses in a Rat Model of Incisional Pain.

Chrysoula C Stachtari et al.

American journal of therapeutics, 23(6), e1484-e1492 (2014-11-06)

The aim of this study was to elucidate the antinociceptive interaction between cannabinoids and tramadol and their impact on proinflammatory response, in terms of serum intereleukin-6 (IL-6) and interleukin-2 (IL-2) release, in a rat model of incisional pain. Prospective randomized

Central and peripheral sites of action for CB₂ receptor mediated analgesic activity in chronic inflammatory and neuropathic pain models in rats.

Gin C Hsieh et al.

British journal of pharmacology, 162(2), 428-440 (2010-10-01)

Cannabinoid CB₂ receptor activation by selective agonists has been shown to produce analgesic effects in preclinical models of inflammatory and neuropathic pain. However, mechanisms underlying CB₂-mediated analgesic effects remain largely unknown. The present study was conducted to elucidate the CB₂

Antinociceptive effects of racemic AM1241 and its chirally synthesized enantiomers: lack of dependence upon opioid receptor activation.

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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