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D9446

Sigma-Aldrich

L-DOPS

≥98% (HPLC)

Synonym(s):

Droxidopa, L-threo 3,4-Dihydroxyphenylserine

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About This Item

Empirical Formula (Hill Notation):
C9H11NO5
CAS Number:
23651-95-8
Molecular Weight:
213.19
MDL number:
MFCD00799030
UNSPSC Code:
12352200
PubChem Substance ID:
329798902
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥3 mg/mL

storage temp.

−20°C

SMILES string

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

InChI key

QXWYKJLNLSIPIN-JGVFFNPUSA-N

Gene Information

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

General description

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.

Application

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

Biochem/physiol Actions

L-DOPS is a norepinephrine precursor in vivo.

Features and Benefits

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.

pictograms

Exclamation mark
GHS07

signalword

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
David S Goldstein
Cardiovascular drug reviews, 24(3-4), 189-203 (2007-01-12)
L-threo-3,4-dihydroxyphenylserine (L-DOPS, droxydopa) is a synthetic catecholamino acid. When taken orally, L-DOPS is converted to the sympathetic neurotransmitter, norepinephrine (NE), via decarboxylation catalyzed by L-aromatic-amino-acid decarboxylase (LAAAD). Plasma L-DOPS levels peak at about 3 h, followed by a monoexponential decline
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Articles

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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