JDTic

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JDTic
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Systematic (IUPAC) name
(3R)-7-hydroxy- N-((1S)-1-{[(3R,4R)-4- (3-hydroxyphenyl)- 3,4-dimethylpiperidin- 1-yl]methyl}- 2-methylpropyl)- 1,2,3,4-tetrahydroisoquinoline- 3-carboxamide
Identifiers
CAS Number 361444-66-8
785835-79-2 (hydrochloride)
PubChem CID 9956146
Synonyms JDTic
Chemical data
Formula C28H39N3O3
Molar mass 465.626 g/mol[[Script error: No such module "String".]]
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JDTic is a drug that acts as an opioid antagonist, which is highly selective for the κ-opioid receptor, and blocks this receptor without affecting the μ- or δ-opioid receptors.[1] It is a 4-phenylpiperidine derivative, distantly structurally related to analgesic drugs such as meperidine and ketobemidone, and more closely to the mu opioid antagonist alvimopan, and is structurally distinct from other kappa antagonists such as norbinaltorphimine.[2][3] It has a very long duration of action, with effects in animals seen for up to several weeks after administration of a single dose,[4] although its binding to the kappa opioid receptor is not irreversible and its long-acting effects are instead caused by altered activity of c-Jun N-terminal kinases.[5] Animal studies suggest that it may produce antidepressant and anxiolytic effects,[6] as well as having possible application in the treatment of addiction to cocaine and morphine.[7][8]

References

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  1. ↑ Thomas JB, Atkinson RN, Rothman RB, Fix SE, Mascarella SW, Vinson NA, Xu H, Dersch CM, Lu Y, Cantrell BE, Zimmerman DM, Carroll FI. Identification of the first trans-(3R,4R)- dimethyl-4-(3-hydroxyphenyl)piperidine derivative to possess highly potent and selective opioid kappa receptor antagonist activity. Journal of Medicinal Chemistry. 2001 Aug 16;44(17):2687-90. PMID 11495579
  2. ↑ Thomas JB, Atkinson RN, Vinson NA, Catanzaro JL, Perretta CL, Fix SE, Mascarella SW, Rothman RB, Xu H, Dersch CM, Cantrell BE, Zimmerman DM, Carroll FI. 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. Journal of Medicinal Chemistry. 2003 Jul 3;46(14):3127-37. PMID 12825951
  3. ↑ Cai TB, Zou Z, Thomas JB, Brieaddy L, Navarro HA, Carroll FI. 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). Journal of Medicinal Chemistry. 2008 Mar 27;51(6):1849-60. PMID 18307295
  4. ↑ Carroll FI, Thomas JB, Dykstra LA, Granger AL, Allen RM, Howard JL, Pollard GT, Aceto MD, Harris LS. Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist. European Journal of Pharmacology. 2004 Oct 6;501(1-3):111-9. PMID 15464069
  5. ↑ Bruchas MR, Yang T, Schreiber S, Defino M, Kwan SC, Li S, Chavkin C. Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase. Journal of Biological Chemistry. 2007 Oct 12;282(41):29803-11. PMID 17702750
  6. ↑ Knoll AT, Meloni EG, Thomas JB, Carroll FI, Carlezon WA Jr. Anxiolytic-like effects of kappa-opioid receptor antagonists in models of unlearned and learned fear in rats. Journal of Pharmacology and Experimental Therapeutics. 2007 Dec;323(3):838-45. PMID 17823306
  7. ↑ Beardsley PM, Howard JL, Shelton KL, Carroll FI. 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. Psychopharmacology (Berlin). 2005 Nov;183(1):118-26. PMID 16184376
  8. ↑ Carroll FI, Harris LS, Aceto MD. 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. European Journal of Pharmacology. 2005 Nov 7;524(1-3):89-94. PMID 16236279
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