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SML0327

Sigma-Aldrich

AM630

≥90% (HPLC)

Synonym(s):

6-Iodo-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl](4-methoxyphenyl)methanone, AM 630, Iodopravadoline

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About This Item

Empirical Formula (Hill Notation):
C23H25IN2O3
CAS Number:
164178-33-0
Molecular Weight:
504.36
MDL number:
MFCD01861183
UNSPSC Code:
12352200
PubChem Substance ID:
329825332
NACRES:
NA.77

Quality Level

100

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.

Biochem/physiol Actions

AM630 is a selective CB2 cannabinoid antagonist/inverse agonist (Ki = 31.2 nM) with > 150-fold selectivity over CB1 receptors.
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).

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
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
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
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
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
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