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
| Molecular Formula | C28H39N3O3 |
| Molecular Weight | 465.6276 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity. | 2001 Aug 16 |
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| Importance of phenolic address groups in opioid kappa receptor selective antagonists. | 2004 Feb 12 |
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| Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist. | 2004 Oct 6 |
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| Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase. | 2007 Oct 12 |
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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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 12:02:12 GMT 2023
by
admin
on
Sat Dec 16 12:02:12 GMT 2023
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| Record UNII |
VR27M77CW3
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| Record Status |
Validated (UNII)
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| Record Version |
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Download
| Name | Type | Language | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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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
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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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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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66576991
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DTXSID70735337
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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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