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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
Structure of JDTIC DIHYDROCHLORIDE

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

HIDE SMILES / InChI
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
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

Description
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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.
2010-07-22
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.
2010-06
Role of kappa-opioid receptors in the effects of salvinorin A and ketamine on attention in rats.
2010-06
Kappa opioid mediation of cannabinoid effects of the potent hallucinogen, salvinorin A, in rodents.
2010-06
Effect of the selective kappa-opioid receptor antagonist JDTic on nicotine antinociception, reward, and withdrawal in the mouse.
2010-06
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).
2009-12-10
[11C]-MeJDTic: a novel radioligand for kappa-opioid receptor positron emission tomography imaging.
2008-07
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).
2008-03-27
Anxiolytic-like effects of kappa-opioid receptor antagonists in models of unlearned and learned fear in rats.
2007-12
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.
2007-10-13
Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase.
2007-10-12
Kappa receptor bivalent ligands.
2007
Effects of JDTic, a selective kappa-opioid receptor antagonist, on the development and expression of physical dependence on morphine using a rat continuous-infusion model.
2005-11-07
Differential effects of the novel kappa opioid receptor antagonist, JDTic, on reinstatement of cocaine-seeking induced by footshock stressors vs cocaine primes and its antidepressant-like effects in rats.
2005-11
Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist.
2004-10-06
Importance of phenolic address groups in opioid kappa receptor selective antagonists.
2004-02-12
Identification 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 as a novel potent and selective opioid kappa receptor antagonist.
2003-07-03
Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity.
2001-08-16
Patents

Patents

06974824
2
20020132828
2

Sample Use Guides

In Vivo Use Guide
Single dose: 1 mg, 3 mg, or 10 mg
Route of Administration: Oral
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 Tue Apr 01 17:49:09 GMT 2025
Edited
by admin
on Tue Apr 01 17:49:09 GMT 2025
Record UNII
VR27M77CW3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JDTIC DIHYDROCHLORIDE
Common Name English
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)-
Preferred Name English
JDTIC HYDROCHLORIDE
Common Name English
(3R)-7-HYDROXY-N-((1S)-1-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDYL)METHYL)-2-METHYL-PROPYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXAMIDE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
MANUFACTURER PRODUCT INFORMATION
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 Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
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
FDA UNII
VR27M77CW3
Created by admin on Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
PRIMARY
CLINICAL_TRIALS.GOV
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 Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
PRIMARY This study has been terminated.(No further subjects will be enrolled due to adverse events.)
CAS
785835-79-2
Created by admin on Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
PRIMARY
PUBCHEM
66576991
Created by admin on Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID70735337
Created by admin on Tue Apr 01 17:49:09 GMT 2025 , Edited by admin on Tue Apr 01 17:49:09 GMT 2025
PRIMARY
Related Record Type Details
Structure of JDTIC
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