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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

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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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
Horacio Kaufmann et al.
Neurology, 83(4), 328-335 (2014-06-20)
To determine whether droxidopa, an oral norepinephrine precursor, improves symptomatic neurogenic orthostatic hypotension (nOH). Patients with symptomatic nOH due to Parkinson disease, multiple system atrophy, pure autonomic failure, or nondiabetic autonomic neuropathy underwent open-label droxidopa dose optimization (100-600 mg 3
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
Jill M Wecht et al.
Archives of physical medicine and rehabilitation, 94(10), 2006-2012 (2013-04-23)
To determine the effect of an escalating dose of droxidopa (100, 200, and 400 mg) compared with placebo on seated blood pressure (BP) in hypotensive individuals with spinal cord injury (SCI). Secondarily, we aimed to determine the effect of droxidopa
Kafui Dzirasa et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(18), 6387-6397 (2010-05-07)
Although normal dopaminergic tone has been shown to be essential for the induction of cortico-striatal and mesolimbic theta oscillatory activity, the influence of norepinephrine on these brain networks remains relatively unknown. To address this question, we simultaneously recorded local field
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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.

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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