Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C28H39N3O3.2ClH |
| Molecular Weight | 538.549 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CC(C)[C@@H](CN1CC[C@](C)([C@@H](C)C1)C2=CC(O)=CC=C2)NC(=O)[C@H]3CC4=CC=C(O)C=C4CN3
InChI
InChIKey=QJNHURYCTCUGHH-AVWZHOAASA-N
InChI=1S/C28H39N3O3.2ClH/c1-18(2)26(30-27(34)25-13-20-8-9-24(33)12-21(20)15-29-25)17-31-11-10-28(4,19(3)16-31)22-6-5-7-23(32)14-22;;/h5-9,12,14,18-19,25-26,29,32-33H,10-11,13,15-17H2,1-4H3,(H,30,34);2*1H/t19-,25+,26+,28+;;/m0../s1
DescriptionCurator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01431586?term=JDTIC&rank=1
Curator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01431586?term=JDTIC&rank=1
JDTic demonstrated high affinity for the kappa opioid receptor in the binding assay and highly potent and selective kappa antagonism in the [(35)S]GTP-gamma-S assay. This drug was in phase I of clinical trials for the treatment of cocaine abuse, but development was stopped because of incidence of non-sustained ventricular tachycardia.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Kappa receptor bivalent ligands. | 2007 |
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| Anxiolytic-like effects of kappa-opioid receptor antagonists in models of unlearned and learned fear in rats. | 2007 Dec |
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| In vivo rat brain opioid receptor binding of LY255582 assessed with a novel method using LC/MS/MS and the administration of three tracers simultaneously. | 2007 Oct 13 |
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| [11C]-MeJDTic: a novel radioligand for kappa-opioid receptor positron emission tomography imaging. | 2008 Jul |
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| Synthesis and in vitro opioid receptor functional antagonism of analogues of the selective kappa opioid receptor antagonist (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). | 2008 Mar 27 |
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| Synthesis and in vitro opioid receptor functional antagonism of methyl-substituted analogues of (3R)-7-hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). | 2009 Dec 10 |
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| Analogues of (3R)-7-hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in vitro and in vivo opioid receptor antagonist activity. | 2010 Jul 22 |
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| Effectiveness of analogs of the kappa opioid receptor antagonist (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic) to reduce U50,488-induced diuresis and stress-induced cocaine reinstatement in rats. | 2010 Jun |
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| Role of kappa-opioid receptors in the effects of salvinorin A and ketamine on attention in rats. | 2010 Jun |
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| Kappa opioid mediation of cannabinoid effects of the potent hallucinogen, salvinorin A, in rodents. | 2010 Jun |
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| Effect of the selective kappa-opioid receptor antagonist JDTic on nicotine antinociception, reward, and withdrawal in the mouse. | 2010 Jun |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: JDTic demonstrated high affinity for the κ receptor in the binding assay and highly potent and selective κ antagonism in the [35S]GTP-γ-S assay. In the [35S]GTP-γ-S functional assay, JDTic demonstrated a 3.4-fold increase in κ antagonist potency relative to the functional assay utilizing guinea pig membranes.
Unknown
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Common Name | English |
| Code System | Code | Type | Description | ||
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3-ISOQUINOLINECARBOXAMIDE, 1,2,3,4-TETRAHYDRO-7-HYDROXY-N-((1S)-1-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-2-METHYLPROPYL)-, HYDROCHLORIDE (1:2), (3R)-
Created by
admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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PRIMARY | Biological Activity:; Description: JDTic is a selective inhibitor of kappa opioid receptor with IC50 value of 0.02 nM.; Target: kappa opioid receptor with an IC50 0.02 NM; Cell experiment:, Cell line: HEK293 cells expressing KOPr-GFP | ||
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VR27M77CW3
Created by
admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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3-ISOQUINOLINECARBOXAMIDE, 1,2,3,4-TETRAHYDRO-7-HYDROXY-N-((1S)-1-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-2-METHYLPROPYL)-, HYDROCHLORIDE (1:2), (3R)-
Created by
admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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PRIMARY | This study has been terminated.(No further subjects will be enrolled due to adverse events.) | ||
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785835-79-2
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admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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66576991
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admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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DTXSID70735337
Created by
admin on Sat Dec 16 12:02:13 GMT 2023 , Edited by admin on Sat Dec 16 12:02:13 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
