JDTIC DIHYDROCHLORIDE

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 Search

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

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Cocaine addiction 28 Sources: https://clinicaltrials.gov/ct2/show/NCT01431586	Primary		Withdrawn	Unknown Approved Use Unknown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
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
[11C]-MeJDTic: a novel radioligand for kappa-opioid receptor positron emission tomography imaging.	2008 Jul	18589300
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
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	19954245
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	20372878
Effect of the selective kappa-opioid receptor antagonist JDTic on nicotine antinociception, reward, and withdrawal in the mouse.	2010 Jun	20232057

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 DIHYDROCHLORIDE

Common 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

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)-

Common 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)-