JDTIC

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H39N3O3
Molecular Weight	465.6276
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@@H](CN1CC[C@](C)([C@@H](C)C1)C2=CC(O)=CC=C2)NC(=O)[C@H]3CC4=C(CN3)C=C(O)C=C4

InChI

InChIKey=ZLVXBBHTMQJRSX-VMGNSXQWSA-N

InChI=1S/C28H39N3O3/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)/t19-,25+,26+,28+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11495579
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

Targets

Primary Target	Pharmacology	Condition	Potency
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11495579	Antagonist 2778		0.3 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cocaine addiction 28 Sources: https://clinicaltrials.gov/ct2/show/NCT01431586	Primary		Withdrawn	Unknown Approved Use Unknown

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	11495579
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 Jul 3	12825951
Importance of phenolic address groups in opioid kappa receptor selective antagonists.	2004 Feb 12	14761209
Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist.	2004 Oct 6	15464069
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 Nov	16184376
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 Nov 7	16236279
Kappa receptor bivalent ligands.	2007	17305578
Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase.	2007 Oct 12	17702750
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	17935738
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	18307295
Role of kappa-opioid receptors in the effects of salvinorin A and ketamine on attention in rats.	2010 Jun	20358363

Patents

Sample Use Guides

In Vivo Use Guide

Single dose: 1 mg, 3 mg, or 10 mg

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

JDTIC

Common Name

English

RTI-JDTIC

Common Name

English

(3R)-7-HYDROXY-N-((2S)-1-((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYLPIPERIDIN-1-YL)-3-METHYLBUTAN-2-YL)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXAMIDE

Systematic 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)-, (3R)-

Systematic Name

English

Code System Code Type Description

CAS

361444-66-8