SML0327

Sigma-Aldrich

AM630

≥90% (HPLC)

Sinónimos:
6-Iodo-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl](4-methoxyphenyl)methanone, AM 630, Iodopravadoline
Empirical Formula (Hill Notation):
C23H25IN2O3
Número de CAS:
Peso molecular:
504.36
MDL number:
PubChem Substance ID:
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Quality Level

assay

≥90% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)C(=O)c2c(C)n(CCN3CCOCC3)c4cc(I)ccc24

InChI

1S/C23H25IN2O3/c1-16-22(23(27)17-3-6-19(28-2)7-4-17)20-8-5-18(24)15-21(20)26(16)10-9-25-11-13-29-14-12-25/h3-8,15H,9-14H2,1-2H3

InChI key

JHOTYHDSLIUKCJ-UHFFFAOYSA-N

Application

AM630 has been used:
  • as a cannabinoid 2(CB2) inhibitor to study the analgesic effect exerted by polysaccharopeptide from Trametes versicolor (TPSP).
  • as a CB2 antagonist along with β-caryophyllene (BCP) to study its effects on re-epithilialization of fibroblast cells.
  • as a CB2 antagonist to study its interaction with 17-β-estradiol in primary human osteoblasts.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

AM630 is an aminoalkylindole and acts as a competitive antagonist of CP 55,940 and WIN 55,212-2. It also behaves as a competitive antagonist of anandamide and (R)-(+)-arachidonyl-1′-hydroxy-2′-propylamide (AM356).
AM630 is a selective CB2 cannabinoid antagonist/inverse agonist (Ki = 31.2 nM) with > 150-fold selectivity over CB1 receptors.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Environment

signalword

Warning

hcodes

RIDADR

UN 3077 9 / PGIII

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

R Pertwee et al.
Life sciences, 56(23-24), 1949-1955 (1995-01-01)
AM630 (iodopravadoline), a novel aminoalkylindole, has been found to attenuate the ability of a number of cannabinoids to inhibit electrically-evoked twitches of the mouse isolated vas deferens. It did not block the inhibitory effects of morphine or clonidine on the...
Marko Hojnik et al.
Biomedical reports, 3(4), 554-558 (2015-07-15)
The bone remodeling process is influenced by various factors, including estrogens and transmitters of the endocannabinoid system. In osteoblasts, cannabinoid receptors 2 (CB-2) are expressed at a much higher level compared to CB-1 receptors. Previous studies have shown that estrogens...
K A Jenkin et al.
British journal of pharmacology, 173(7), 1128-1142 (2014-12-30)
In diabetic nephropathy agonism of CB2 receptors reduces albuminuria and podocyte loss; however, the role of CB2 receptors in obesity-related nephropathy is unknown. The aim of this study was to determine the role of CB2 receptors in a model of...
Massimo Nabissi et al.
Oncotarget, 7(47), 77543-77557 (2016-10-22)
Several studies showed a potential anti-tumor role for cannabinoids, by modulating cell signaling pathways involved in cancer cell proliferation, chemo-resistance and migration. Cannabidiol (CBD) was previously noted in multiple myeloma (MM), both alone and in synergy with the proteasome inhibitor...
Sachiko Koyama et al.
PloS one, 14(12), e0216104-e0216104 (2019-12-17)
Beta-caryophyllene is an odoriferous bicyclic sesquiterpene found in various herbs and spices. Recently, it was found that beta-caryophyllene is a ligand of the cannabinoid receptor 2 (CB2). Activation of CB2 will decrease pain, a major signal for inflammatory responses. We...

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