Nepicastat hydrochloride monohydrate | CAS# 177645-08-8 | Biochemical

MedKoo Cat#: 578090 | Name: Nepicastat hydrochloride monohydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nepicastat hydrochloride monohydrate is an inhibitor of dopamine beta-hydroxylase, an enzyme that catalyzes the conversion of dopamine to norepinephrine.

Chemical Structure

Nepicastat hydrochloride monohydrate

CAS#177645-08-8 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 578090

Name: Nepicastat hydrochloride monohydrate

CAS#: 177645-08-8 (HCl hydrate)

Chemical Formula: C14H18ClF2N3OS

Exact Mass: 349.0827

Molecular Weight: 349.82

Elemental Analysis: C, 48.07; H, 5.19; Cl, 10.13; F, 10.86; N, 12.01; O, 4.57; S, 9.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

170151-24-3 (HCl) 173997-05-2 (free base) 195881-94-8 (HCl R isomer) 177645-08-8 (HCl hydrate)

Synonym

Nepicastat hydrochloride monohydrate; Nepicastat HCl monohydrate; Nepicastat HCl hydrate

IUPAC/Chemical Name

2h-imidazole-2-thione, 5-(aminomethyl)-1-(5,7-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)-1,3-dihydro-, monohydrochloride, monohydrate, (s)-

InChi Key

AILBEJJAAWNNIR-XRIOVQLTSA-N

InChi Code

InChI=1S/C14H15F2N3S.ClH.H2O/c15-9-3-8-4-10(1-2-12(8)13(16)5-9)19-11(6-17)7-18-14(19)20;;/h3,5,7,10H,1-2,4,6,17H2,(H,18,20);1H;1H2/t10-;;/m0../s1

SMILES Code

O.Cl.NCC1=CNC(=S)N1[C@H]2CCc3c(F)cc(F)cc3C2

Appearance

Solid powder

Purity

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

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 349.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Catelas DN, Serrão MP, Soares-Da-Silva P. Effects of nepicastat upon dopamine-β-hydroxylase activity and dopamine and norepinephrine levels in the rat left ventricle, kidney, and adrenal gland. Clin Exp Hypertens. 2020;42(2):118-125. doi: 10.1080/10641963.2019.1583245. Epub 2019 Mar 1. PMID: 30821508. 2: Colombo G, Maccioni P, Vargiolu D, Loi B, Lobina C, Zaru A, Carai MA, Gessa GL. The dopamine β-hydroxylase inhibitor, nepicastat, reduces different alcohol- related behaviors in rats. Alcohol Clin Exp Res. 2014 Sep;38(9):2345-53. doi: 10.1111/acer.12520. PMID: 25257286. 3: 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. PMID: 23303068; PMCID: PMC3629392. 4: Stanley WC, Lee K, Johnson LG, Whiting RL, Eglen RM, Hegde SS. Cardiovascular effects of nepicastat (RS-25560-197), a novel dopamine beta-hydroxylase inhibitor. J Cardiovasc Pharmacol. 1998 Jun;31(6):963-70. doi: 10.1097/00005344-199806000-00023. PMID: 9641484. 5: De La Garza R 2nd, Bubar MJ, Carbone CL, Moeller FG, Newton TF, Anastasio NC, Harper TA, Ware DL, Fuller MA, Holstein GJ, Jayroe JB, Bandak SI, Reiman KZ, Neale AC, Pickford LB, Cunningham KA. Evaluation of the dopamine β-hydroxylase (DβH) inhibitor nepicastat in participants who meet criteria for cocaine use disorder. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Jun 3;59:40-48. doi: 10.1016/j.pnpbp.2015.01.009. Epub 2015 Jan 17. PMID: 25602710; PMCID: PMC4777897. 6: 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. PMID: 23561307. 7: 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. PMID: 23289939. 8: Stanley WC, Li B, Bonhaus DW, Johnson LG, Lee K, Porter S, Walker K, Martinez G, Eglen RM, Whiting RL, Hegde SS. Catecholamine modulatory effects of nepicastat (RS-25560-197), a novel, potent and selective inhibitor of dopamine- beta-hydroxylase. Br J Pharmacol. 1997 Aug;121(8):1803-9. doi: 10.1038/sj.bjp.0701315. PMID: 9283721; PMCID: PMC1564872. 9: Bonifácio MJ, Sousa F, Neves M, Palma N, Igreja B, Pires NM, Wright LC, Soares-da-Silva P. Characterization of the interaction of the novel antihypertensive etamicastat with human dopamine-β-hydroxylase: comparison with nepicastat. Eur J Pharmacol. 2015 Mar 15;751:50-8. doi: 10.1016/j.ejphar.2015.01.034. Epub 2015 Jan 29. PMID: 25641750. 10: Loureiro AI, Bonifácio MJ, Fernandes-Lopes C, Pires N, Igreja B, Wright LC, Soares-da-Silva P. Role of P-glycoprotein and permeability upon the brain distribution and pharmacodynamics of etamicastat: a comparison with nepicastat. Xenobiotica. 2015;45(9):828-39. doi: 10.3109/00498254.2015.1018985. Epub 2015 Jun 10. PMID: 25915108.