Nepicastat, also known as SYN117 and RS-25560-197, is an inhibitor of dopamine beta-hydroxylase, an enzyme that catalyzes the conversion of dopamine to norepinephrine. It has been studied as a possible treatment for congestive heart failure, and appears to be well tolerated. As of 2012, clinical trials to assess nepicastat as a treatment for post-traumatic stress disorder (PTSD) and cocaine dependence have been completed. In Phase 2 study treatment with nepicastat was not effective in relieving PTSD-associated symptoms when compared to placebo.

MedKoo Cat#: 510304 Name: Nepicastat HCl CAS#: 170151-24-3 (HCl) Chemical Formula: C14H15F2N3S Exact Mass: Molecular Weight: 295.35 Elemental Analysis: C, 56.93; H, 5.12; F, 12.86; N, 14.23; S, 10.86

Related CAS #: 170151-24-3 (HCl) 173997-05-2 (free base) 195881-94-8 (HCl R isomer)

Synonym: SYN117; SYN-117; SYN 117; RS25560197; RS25560-197; RS-25560-197; RS 25560-197; Nepicastat; Nepicastat HCl

IUPAC/Chemical Name: (S)-5-(aminomethyl)-1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1H-imidazole-2(3H)-thione hydrochloride

InChi Key: DIPDUAJWNBEVOY-PPHPATTJSA-N

InChi Code: InChI=1S/C14H15F2N3S.ClH/c15-9-3-8-4-10(1-2-12(8)13(16)5-9)19-11(6-17)7-18-14(19)20;/h4,5,7,10H,1-2,4,6,17H2,(H,18,20);1H/t10-;/m0./s1

SMILES Code: S=C1NC=C(CN)N1[C@@H]2CC3=C(C(F)=CC(F)=C3)CC2.[H]Cl

Technical Data

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: current batch, Lot#BBC70417

QC Data: View QC data: current batch, Lot#BBC70417

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

  Related CAS# 170151-24-3 ( Nepicastat HCl); 173997-05-2 ( Nepicastat free base).       

References

1: Devoto P, Fattore L, Antinori S, Saba P, Frau R, Fratta W, Gessa GL. Elevated dopamine in the medial prefrontal cortex suppresses cocaine seeking via D1 receptor overstimulation. Addict Biol. 2014 Aug 19. doi: 10.1111/adb.12178. [Epub ahead of print] PubMed PMID: 25135633.

2: Cooper DA, Kimmel HL, Manvich DF, Schmidt KT, Weinshenker D, Howell LL. Effects of pharmacologic dopamine β-hydroxylase inhibition on cocaine-induced reinstatement and dopamine neurochemistry in squirrel monkeys. J Pharmacol Exp Ther. 2014 Jul;350(1):144-52. doi: 10.1124/jpet.113.212357. Epub 2014 May 9. PubMed PMID: 24817036; PubMed Central PMCID: PMC4056266.

3: Manvich DF, DePoy LM, Weinshenker D. Dopamine β-hydroxylase inhibitors enhance the discriminative stimulus effects of cocaine in rats. J Pharmacol Exp Ther. 2013 Dec;347(3):564-73. doi: 10.1124/jpet.113.207746. Epub 2013 Sep 25. PubMed PMID: 24068832; PubMed Central PMCID: PMC3836309.

4: Zaru A, Maccioni P, Colombo G, Gessa GL. The dopamine β-hydroxylase inhibitor, nepicastat, suppresses chocolate self-administration and reinstatement of chocolate seeking in rats. Br J Nutr. 2013 Oct;110(8):1524-33. doi: 10.1017/S0007114513000743. Epub 2013 Apr 8. PubMed PMID: 23561307.

5: Schroeder JP, Epps SA, Grice TW, Weinshenker D. The selective dopamine β-hydroxylase inhibitor nepicastat attenuates multiple aspects of cocaine-seeking behavior. Neuropsychopharmacology. 2013 May;38(6):1032-8. doi: 10.1038/npp.2012.267. Epub 2013 Jan 3. PubMed PMID: 23303068; PubMed Central PMCID: PMC3629392.

6: Devoto P, Flore G, Saba P, Bini V, Gessa GL. The dopamine beta-hydroxylase inhibitor nepicastat increases dopamine release and potentiates psychostimulant-induced dopamine release in the prefrontal cortex. Addict Biol. 2014 Jul;19(4):612-22. doi: 10.1111/adb.12026. Epub 2013 Jan 7. PubMed PMID: 23289939.

7: Gaval-Cruz M, Liles LC, Iuvone PM, Weinshenker D. Chronic inhibition of dopamine β-hydroxylase facilitates behavioral responses to cocaine in mice. PLoS One. 2012;7(11):e50583. doi: 10.1371/journal.pone.0050583. Epub 2012 Nov 27. PubMed PMID: 23209785; PubMed Central PMCID: PMC3507785.

8: Kapoor A, Shandilya M, Kundu S. Structural insight of dopamine β-hydroxylase, a drug target for complex traits, and functional significance of exonic single nucleotide polymorphisms. PLoS One. 2011;6(10):e26509. doi: 10.1371/journal.pone.0026509. Epub 2011 Oct 20. PubMed PMID: 22028891; PubMed Central PMCID: PMC3197665.

9: Schroeder JP, Cooper DA, Schank JR, Lyle MA, Gaval-Cruz M, Ogbonmwan YE, Pozdeyev N, Freeman KG, Iuvone PM, Edwards GL, Holmes PV, Weinshenker D. Disulfiram attenuates drug-primed reinstatement of cocaine seeking via inhibition of dopamine β-hydroxylase. Neuropsychopharmacology. 2010 Nov;35(12):2440-9. doi: 10.1038/npp.2010.127. Epub 2010 Aug 25. PubMed PMID: 20736996; PubMed Central PMCID: PMC2956132.

10: Gaval-Cruz M, Schroeder JP, Liles LC, Javors MA, Weinshenker D. Effects of disulfiram and dopamine beta-hydroxylase knockout on cocaine-induced seizures. Pharmacol Biochem Behav. 2008 Jun;89(4):556-62. doi: 10.1016/j.pbb.2008.02.009. Epub 2008 Feb 12. PubMed PMID: 18329701; PubMed Central PMCID: PMC2386143.

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