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A6478

Sigma-Aldrich

(R,S)-AM1241

≥98% (HPLC), solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C22H22IN3O3
Numéro CAS:
444912-48-5
Poids moléculaire :
503.33
Numéro MDL:
MFCD11045986
Code UNSPSC :
12352200
ID de substance PubChem :
24891092
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Couleur

yellow

Solubilité

DMSO: ~18 mg/mL at 60 °C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H334,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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)
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
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)
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