Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H25IN2O3 |
| Molecular Weight | 504.3607 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C(=O)C2=C(C)N(CCN3CCOCC3)C4=CC(I)=CC=C24
InChI
InChIKey=JHOTYHDSLIUKCJ-UHFFFAOYSA-N
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
| Molecular Formula | C23H25IN2O3 |
| Molecular Weight | 504.3607 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
6-Iodopravadoline (AM-630) is a cannabinoid receptor antagonist under development with the Univerisity of Wisconsin, USA, for potential use in the treatment of Anorexia nervosa. AM-630 is a selective CB2 receptor antagonist that binds to CB1 and CB2 receptors with Ki values of 5.2 μM and 31.2 nM, respectively. AM630 has been shown to display 165-fold selectivity over CB1 receptors and behave as a weak partial/inverse agonist at CB1 receptors. AM-630 acts as an inverse agonist on cloned human CB1 receptors. The efficacy of AM-630 in reducing the anxiety of the spontaneously anxious DBA/2 strain of mice strengthens the potential of the CB(2) receptor as a new target in the treatment of anxiety-related disorders.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630. | 1999 Feb |
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| Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells. | 2006 Apr |
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| Effect of anandamide on nonadrenergic noncholinergic-mediated relaxation of rat corpus cavernosum. | 2006 Aug 21 |
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| 2-Arachidonylglycerol acting on CB1 cannabinoid receptors mediates delayed cardioprotection induced by nitric oxide in rat isolated hearts. | 2006 May |
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| Transcriptional regulation of the cannabinoid receptor type 1 gene in T cells by cannabinoids. | 2007 Jan |
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| Cannabinoid (CB1) receptor activation inhibits trigeminovascular neurons. | 2007 Jan |
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| Cannabinoids ameliorate pain and reduce disease pathology in cerulein-induced acute pancreatitis. | 2007 May |
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| The cannabinoid delta(9)-tetrahydrocannabinol inhibits RAS-MAPK and PI3K-AKT survival signalling and induces BAD-mediated apoptosis in colorectal cancer cells. | 2007 Nov 15 |
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| MDA7: a novel selective agonist for CB2 receptors that prevents allodynia in rat neuropathic pain models. | 2008 Dec |
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| Inhibition of cancer cell invasion by cannabinoids via increased expression of tissue inhibitor of matrix metalloproteinases-1. | 2008 Jan 2 |
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| Effect of cannabinoids upon the uptake of folic acid by BeWo cells. | 2009 |
|
| Delta9-tetrahydrocannabinol and cannabidiol modulate mitogen-induced tryptophan degradation and neopterin formation in peripheral blood mononuclear cells in vitro. | 2009 Feb 15 |
|
| Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging. | 2009 Jan |
|
| Investigations on the 4-quinolone-3-carboxylic acid motif. 4. Identification of new potent and selective ligands for the cannabinoid type 2 receptor with diverse substitution patterns and antihyperalgesic effects in mice. | 2011 Aug 11 |
|
| Cannabidiol inhibits lung cancer cell invasion and metastasis via intercellular adhesion molecule-1. | 2012 Apr |
|
| Cannabinoid receptor-2 (CB2) agonist ameliorates colitis in IL-10(-/-) mice by attenuating the activation of T cells and promoting their apoptosis. | 2012 Jan 15 |
|
| Cannabinoid-induced enhanced interaction and protein levels of serotonin 5-HT(2A) and dopamine D₂ receptors in rat prefrontal cortex. | 2012 Oct |
|
| Cannabinoid receptor agonists upregulate and enhance serotonin 2A (5-HT(2A)) receptor activity via ERK1/2 signaling. | 2013 Mar |
|
| Cytotoxicity of synthetic cannabinoids on primary neuronal cells of the forebrain: the involvement of cannabinoid CB1 receptors and apoptotic cell death. | 2014 Jan 1 |
|
| The psychoactive compound of Cannabis sativa, Δ(9)-tetrahydrocannabinol (THC) inhibits the human trophoblast cell turnover. | 2015 Aug 6 |
Patents
Sample Use Guides
Mice: 6-Iodopravadoline (AM-630) (2, 3 mg/kg, i.p.) significantly reduces the time spent in the light box compared with vehicle group. AM-630 increases anxiety since the time spent in the light box is reduced compared with its corresponding control group. AM-630 (1, 2 or 3 mg/kg, i.p., twice a day) produces a significant anxiolytic effect, increasing the time spent in the light box at all of the doses used.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Curator's Comment: Binding assays with membranes from CHO cells stably transfected with human CB1 or CB2 receptors were used.
6-Iodopravadoline (AM-630) inhibited [35S]-GTPgammaS binding to CB2 receptor membranes (EC50 = 76.6 nM), enhanced forskolin-stimulated cyclic AMP production in CB2-transfected cells (5.2 fold by 1 uM), and antagonized the inhibition of forskolin-stimulated cyclic AMP production in this cell line induced by CP55940. In CB1-transfected cells, forskolin-stimulated cyclic AMP production was significantly inhibited by AM-630 (22.6% at 1 uM and 45.9% at 10 uM).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:16:31 UTC 2023
by
admin
on
Sat Dec 16 09:16:31 UTC 2023
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| Record UNII |
U1LNJ6NBKA
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| Record Status |
Validated (UNII)
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| Record Version |
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WIKIPEDIA |
Designer-drugs-AM-630
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admin on Sat Dec 16 09:16:31 UTC 2023 , Edited by admin on Sat Dec 16 09:16:31 UTC 2023
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164178-33-0
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AM-630
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U1LNJ6NBKA
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DTXSID10167719
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4302963
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ACTIVE MOIETY |
