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D9446

Sigma-Aldrich

L-DOPS

≥98% (HPLC)

Sinónimos:

Droxidopa, L-threo 3,4-Dihydroxyphenylserine

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About This Item

Fórmula empírica (notación de Hill):
C9H11NO5
Número de CAS:
23651-95-8
Peso molecular:
213.19
Número MDL:
MFCD00799030
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329798902
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

white to tan

solubilidad

DMSO: ≥3 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

N[C@@H]([C@H](O)c1ccc(O)c(O)c1)C(O)=O

InChI

1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1

Clave InChI

QXWYKJLNLSIPIN-JGVFFNPUSA-N

Información sobre el gen

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , ADRB1(153) , ADRB2(154) , ADRB3(155)

Descripción general

L-DOPS, also called L-threo 3,4-Dihydroxyphenylserine or droxidopa is a catecholamine. L-DOPS has many clinical advantages and may be useful for treating norepinephrine deficiency. It is used for treating neurogenic orthostatic hypotension and improves norepinephrine levels. L-DOPS mediates reduction of amyloid plaques and could have a therapeutic potential for treating amyloid pathology.

Aplicación

L-DOPS has been administered for clinical trial studies in mice with amyloid pathology.

Acciones bioquímicas o fisiológicas

L-DOPS is a norepinephrine precursor in vivo.

Características y beneficios

This compound is featured on the Dopamine, Norepinephrine and Epinephrine Synthesis page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000422237
0000422235
0000422237
0000422235
0000414816

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David S Goldstein et al.
Journal of clinical pharmacology, 51(1), 66-74 (2010-03-12)
L-threo-3,4-dihydroxyphenylserine (L-DOPS), a norepinephrine (NE) prodrug, is investigational for orthostatic hypotension, which occurs commonly in Parkinson's disease. Adjunctive anti-parkinsonian drugs might interact with L-DOPS. We tested whether L-aromatic amino-acid decarboxylase inhibition by carbidopa (CAR) attenuates L-DOPS conversion to NE and
Horacio Kaufmann
Clinical autonomic research : official journal of the Clinical Autonomic Research Society, 18 Suppl 1, 19-24 (2008-04-23)
Neurogenic orthostatic hypotension results from failure to release norepinephrine, the neurotransmitter of sympathetic postganglionic neurons, appropriately upon standing. In double blind, cross over, placebo controlled trials, administration of droxidopa, a synthetic amino acid that is decarboxylated to norepinephrine by the
Courtney Holmes et al.
Clinical chemistry, 56(5), 832-838 (2010-03-09)
L-threo-3,4-dihydroxyphenylserine (L-DOPS, droxidopa) is a norepinephrine (NE) prodrug under development to treat orthostatic hypotension. 3,4-Dihydroxyphenylacetaldehyde (DOPAL), an endogenous catecholaldehyde produced by enzymatic oxidative deamination of dopamine, is toxic to catecholaminergic neurons. Based on the observation of increasing plasma DOPAL after
Christopher J Mathias
Clinical autonomic research : official journal of the Clinical Autonomic Research Society, 18 Suppl 1, 25-29 (2008-04-23)
Neurogenic orthostatic hypotension is a cardinal feature of generalised autonomic failure and commonly is the presenting sign in patients with primary autonomic failure. Orthostatic hypotension can result in considerable morbidity and even mortality and is a major management problem in
Hui-Jeong Gwon et al.
Biotechnology letters, 32(1), 143-149 (2009-09-18)
Diastereoselectivity-enhanced mutants of L: -threonine aldolase (L: -TA) for L: -threo-3,4-dihydroxyphenylserine (L: -threo-DOPS) synthesis were isolated by error-prone PCR followed by a high-throughput screening. The most improved mutant was achieved from the mutant T3-3mm2, showing a 4-fold increase over the
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Artículos

Dopamine, Norepinephrine and Ephinephrine Synthesis

Dopamine-β-hydroxylase is located inside amine storage vesicles of norepinephrine neurons. Dopamine is actively transported from the cytoplasm into the vesicles. As the enzyme is a copper containing protein, its activity can be inhibited by copper chelating agents, such as diethyldithiocarbamate and FLA-63. Inhibition of the enzyme effectively reduces tissue norepinephrine levels.

Dopamine, Norepinephrine and Ephinephrine Synthesis

Dopamine-β-hydroxylase is located inside amine storage vesicles of norepinephrine neurons. Dopamine is actively transported from the cytoplasm into the vesicles. As the enzyme is a copper containing protein, its activity can be inhibited by copper chelating agents, such as diethyldithiocarbamate and FLA-63. Inhibition of the enzyme effectively reduces tissue norepinephrine levels.

Dopamine, Norepinephrine and Ephinephrine Synthesis

Dopamine-β-hydroxylase is located inside amine storage vesicles of norepinephrine neurons. Dopamine is actively transported from the cytoplasm into the vesicles. As the enzyme is a copper containing protein, its activity can be inhibited by copper chelating agents, such as diethyldithiocarbamate and FLA-63. Inhibition of the enzyme effectively reduces tissue norepinephrine levels.

Dopamine, Norepinephrine and Ephinephrine Synthesis

Dopamine-β-hydroxylase is located inside amine storage vesicles of norepinephrine neurons. Dopamine is actively transported from the cytoplasm into the vesicles. As the enzyme is a copper containing protein, its activity can be inhibited by copper chelating agents, such as diethyldithiocarbamate and FLA-63. Inhibition of the enzyme effectively reduces tissue norepinephrine levels.

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