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Merck
CN

SML0940

Nepicastat hydrochloride

≥95% (HPLC)

Synonym(s):

5-(Aminomethyl)-1-[(2S)-5,7-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl]-1,3-dihydro-2H-imidazole-2-thione hydrochloride, SYN-117

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About This Item

Empirical Formula (Hill Notation):
C14H15F2N3S · HCl
CAS Number:
170151-24-3
Molecular Weight:
331.81
NACRES:
NA.77
PubChem Substance ID:
329825620
UNSPSC Code:
12352200
MDL number:
MFCD00954638

Key Documents

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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;/h3,5,7,10H,1-2,4,6,17H2,(H,18,20);1H/t10-;/m0./s1

SMILES string

FC1=CC2=C(CC[C@H](N3C(CN)=CNC3=S)C2)C(F)=C1.Cl

InChI key

DIPDUAJWNBEVOY-PPHPATTJSA-N

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Application

Nepicastat hydrochloride has been used as an inhibitor of dopamine β-hydroxylase (DBH) in zinc finger protein 521 (ZFP521) deficient mice.

Biochem/physiol Actions

By inhibiting dopamine β-hydroxylase (DβH), nepicastat enhances dopamine levels and norepinephrine levels in brain.
Nepicastat is a potent and selective dopamine β-hydroxylase inhibitor
Nepicastat is a potent and selective dopamine β-hydroxylase inhibitor with an IC50 of 9 nM and negligible affinity (>10 μM) for twelve other enzymes and thirteen neurotransmitter receptors tested. Nepicastat has been shown to attenuate multiple aspects of cocaine-seeking behavior and suppress cocaine-primed reinstatement of cocaine seeking in rats, and has been in clinical trials for cocaine dependence. Nepicastat also suppressed chocolate self-administration and reinstatement of chocolate seeking in rats.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

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GHS07

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000395644
0000324195
0000324195
0000395644
0000289258

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Richard De La Garza et al.
Progress in neuro-psychopharmacology & biological psychiatry, 59, 40-48 (2015-01-21)
In the present study, we tested the hypothesis that the potent and selective dopamine-β-hydroxylase (DβH) inhibitor nepicastat would have minimal effects on cardiovascular and pharmacokinetic parameters associated with cocaine administration and would reduce the positive subjective effects produced by cocaine.
Nobutaka Ohkubo et al.
Life sciences, 231, 116559-116559 (2019-06-15)
Previously, we reported that mice deficient in most of the Zfp521 coding region (Zfp521Δ/Δ mice) displayed abnormal behaviors, including hyperlocomotion and lower anxiety. In this study, we aimed to elucidate the involvement and mechanisms of monoamine variation. First, we compared

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