6-IODOPRAVADOLINE

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

Structure Search

SMILES

COC1=CC=C(C=C1)C(=O)C2=C(C)N(CCN3CCOCC3)C4=C2C=CC(I)=C4

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15556131 | https://www.ncbi.nlm.nih.gov/pubmed/10188977 | https://www.ncbi.nlm.nih.gov/pubmed/21838753 | http://adisinsight.springer.com/drugs/800014985

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

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15556131 \| https://www.ncbi.nlm.nih.gov/pubmed/20218623 \| https://www.ncbi.nlm.nih.gov/pubmed/10188977	Inverse Agonist 85		26.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21838753 https://www.ncbi.nlm.nih.gov/pubmed/23714073	Primary		Preclinical	Unknown Approved Use Unknown
Anorexia nervosa 1 Sources: http://adisinsight.springer.com/drugs/800014985	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The psychoactive compound of Cannabis sativa, Δ(9)-tetrahydrocannabinol (THC) inhibits the human trophoblast cell turnover.	2015-08-06	26070387
Cytotoxicity of synthetic cannabinoids on primary neuronal cells of the forebrain: the involvement of cannabinoid CB1 receptors and apoptotic cell death.	2014-01-01	24211273
Cannabinoid receptor agonists upregulate and enhance serotonin 2A (5-HT(2A)) receptor activity via ERK1/2 signaling.	2013-03	23151877
Cannabinoid-induced enhanced interaction and protein levels of serotonin 5-HT(2A) and dopamine D₂ receptors in rat prefrontal cortex.	2012-10	22791651
Cannabidiol inhibits lung cancer cell invasion and metastasis via intercellular adhesion molecule-1.	2012-04	22198381
Cannabinoid receptor-2 (CB2) agonist ameliorates colitis in IL-10(-/-) mice by attenuating the activation of T cells and promoting their apoptosis.	2012-01-15	22119709
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.	2011-08-11	21702498
Delta9-tetrahydrocannabinol and cannabidiol modulate mitogen-induced tryptophan degradation and neopterin formation in peripheral blood mononuclear cells in vitro.	2009-02-15	19167098
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.	2009-01	18931146
Effect of cannabinoids upon the uptake of folic acid by BeWo cells.	2009	19145103
MDA7: a novel selective agonist for CB2 receptors that prevents allodynia in rat neuropathic pain models.	2008-12	18846037
Inhibition of cancer cell invasion by cannabinoids via increased expression of tissue inhibitor of matrix metalloproteinases-1.	2008-01-02	18159069
The cannabinoid delta(9)-tetrahydrocannabinol inhibits RAS-MAPK and PI3K-AKT survival signalling and induces BAD-mediated apoptosis in colorectal cancer cells.	2007-11-15	17583570
Cannabinoids ameliorate pain and reduce disease pathology in cerulein-induced acute pancreatitis.	2007-05	17484889
Transcriptional regulation of the cannabinoid receptor type 1 gene in T cells by cannabinoids.	2007-01	17041005
Cannabinoid (CB1) receptor activation inhibits trigeminovascular neurons.	2007-01	17018694
Effect of anandamide on nonadrenergic noncholinergic-mediated relaxation of rat corpus cavernosum.	2006-08-21	16824514
2-Arachidonylglycerol acting on CB1 cannabinoid receptors mediates delayed cardioprotection induced by nitric oxide in rat isolated hearts.	2006-05	16775503
Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells.	2006-04	16434616
Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630.	1999-02	10188977

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 22:35:56 GMT 2025` Edited by `admin` on `Mon Mar 31 22:35:56 GMT 2025`
Record UNII	U1LNJ6NBKA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AM-630

Preferred Name

English

6-IODOPRAVADOLINE

Common Name

English

IODOPRAVADOLINE

Common Name

English

METHANONE, (6-IODO-2-METHYL-1-(2-(4-MORPHOLINYL)ETHYL)-1H-INDOL-3-YL)(4-METHOXYPHENYL)-

Systematic Name

English

2-METHYL-3-(4-METHOXYBENZOYL)-6-IODO-1-(2-MORPHOLINOETHYL)-1H-INDOLE

Systematic Name

English

J662.571A

Code

English

1-(2-(MORPHOLIN-4-YL)ETHYL)-2-METHYL-3-(4-METHOXYBENZOYL)-6-IODOINDOLE

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-AM-630