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Merck

SML0940

Sigma-Aldrich

Nepicastat hydrochloride

≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C14H15F2N3S · HCl
Número de CAS:
Peso molecular:
331.81
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

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

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

InChI key

DIPDUAJWNBEVOY-PPHPATTJSA-N

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 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.

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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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
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.

Artículos

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

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