Home Amines 3916-18-5
3916-18-5,MFCD00004266
Catalog No.:AA00BY6T

3916-18-5 | (2RS,3RS)-2-AMINO-3-(3,4-DIHYDROXY-PHENYL)-3-HYDROXY-PROPIONIC ACID

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2.5mg
3 weeks  
$430.00   $301.00
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10mg
3 weeks  
$1,162.00   $813.00
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25mg
3 weeks  
$2,236.00   $1,565.00
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00BY6T
Chemical Name:
(2RS,3RS)-2-AMINO-3-(3,4-DIHYDROXY-PHENYL)-3-HYDROXY-PROPIONIC ACID
CAS Number:
3916-18-5
Molecular Formula:
C9H11NO5
Molecular Weight:
213.1873
MDL Number:
MFCD00004266
SMILES:
OC(=O)C(C(c1ccc(c(c1)O)O)O)N
Properties
Computed Properties
 
Complexity:
235  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
3  
XLogP3:
-3.2  

Literature

Title: Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats.

Journal: Hepatology (Baltimore, Md.) 20121101

Title: The noradrenaline precursor L-DOPS reduces pathology in a mouse model of Alzheimer's disease.

Journal: Neurobiology of aging 20120801

Title: Dopamine dysregulation syndrome including mania related to coadministration of droxidopa.

Journal: Journal of clinical psychopharmacology 20120601

Title: Embryonic lethality in mice lacking mismatch-specific thymine DNA glycosylase is partially prevented by DOPS, a precursor of noradrenaline.

Journal: The Tohoku journal of experimental medicine 20120101

Title: Optimal production of L-threo-2,3-dihydroxyphenylserine (L-threo-DOPS) on a large scale by diastereoselectivity-enhanced variant of L-threonine aldolase expressed in Escherichia coli.

Journal: Preparative biochemistry & biotechnology 20120101

Title: Effects of carbidopa and entacapone on the metabolic fate of the norepinephrine prodrug L-DOPS.

Journal: Journal of clinical pharmacology 20110101

Title: Identification of clinically used drugs that activate pregnane X receptors.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110101

Title: DBH deficiency in an elderly patient: efficacy and safety of chronic droxidopa.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20100601

Title: Noradrenergic control of cortico-striato-thalamic and mesolimbic cross-structural synchrony.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100505

Title: Contamination of the norepinephrine prodrug droxidopa by dihydroxyphenylacetaldehyde.

Journal: Clinical chemistry 20100501

Title: [New perspectives on molecular and genic therapies in Down syndrome].

Journal: Medecine sciences : M/S 20100401

Title: [Pharmacological hypotheses and therapeutic strategies for gait disorders in Parkinson's disease].

Journal: Revue neurologique 20100201

Title: Alpha2-adrenoceptor blockade accelerates the neurogenic, neurotrophic, and behavioral effects of chronic antidepressant treatment.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100120

Title: Diastereoselective synthesis of L: -threo-3,4-dihydroxyphenylserine by low-specific L: -threonine aldolase mutants.

Journal: Biotechnology letters 20100101

Title: Enhanced synthesis of L-threo-3,4-dihydroxyphenylserine by high-density whole-cell biocatalyst of recombinant L-threonine aldolase from Streptomyces avelmitilis.

Journal: Biotechnology letters 20090301

Title: Neurogenic orthostatic hypotension: new prospects in treatment. Introduction.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20080301

Title: L-dihydroxyphenylserine (Droxidopa): a new therapy for neurogenic orthostatic hypotension: the US experience.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20080301

Title: L-dihydroxyphenylserine (Droxidopa) in the treatment of orthostatic hypotension: the European experience.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20080301

Title: Comment on 'Midodrine hydrochloride and L-threo-3,4-dihydroxy-phenylserine preserve cerebral blood flow in hemodialysis patients with orthostatic hypotension' by Fujisaki et al.

Journal: Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20071001

Title: Synthesis of L-threo-3,4-dihydroxyphenylserine (L-threo-DOPS) with thermostabilized low-specific L-threonine aldolase from Streptomyces coelicolor A3(2).

Journal: Journal of microbiology and biotechnology 20070501

Title: Midodrine hydrochloride and L-threo-3,4-dihydroxy-phenylserine preserve cerebral blood flow in hemodialysis patients with orthostatic hypotension.

Journal: Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy 20070201

Title: Noradrenaline is necessary for the hedonic properties of addictive drugs.

Journal: Vascular pharmacology 20061001

Title: Role of noradrenergic signaling by the nucleus tractus solitarius in mediating opiate reward.

Journal: Science (New York, N.Y.) 20060217

Title: The discovery of the pressor effect of DOPS and its blunting by decarboxylase inhibitors.

Journal: Journal of neural transmission. Supplementum 20060101

Title: L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug.

Journal: Cardiovascular drug reviews 20060101

Title: Case report: Marathon runner with severe autonomic failure.

Journal: Lancet (London, England) 20051201

Title: L-DOPS therapy for refractory orthostatic hypotension in autoimmune autonomic neuropathy.

Journal: Neurology 20051011

Title: [Pure akinesia presenting with antecollis].

Journal: No to shinkei = Brain and nerve 20051001

Title: L-threo 3,4-dihydroxyphenylserine treatment during mouse perinatal and rat postnatal development does not alter the impact of dietary copper deficiency.

Journal: Nutritional neuroscience 20050601

Title: [Simple method for precognition of drug interaction between oral iron and phenolic hydroxyl group-containing drugs].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20050201

Title: An explanation of the unexpected efficacy of L-DOPS in pure autonomic failure.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20041201

Title: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20041201

Title: Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20040525

Title: Norepinephrine precursor therapy in neurogenic orthostatic hypotension.

Journal: Circulation 20030812

Title: [Human striatal D-neurons and their significance].

Journal: Nihon shinkei seishin yakurigaku zasshi = Japanese journal of psychopharmacology 20020801

Title: Behavior of fluorinated analogs of L-(3,4-dihydroxyphenyl)alanine and L-threo-(3,4-dihydroxyphenyl)serine as substrates for Dopa decarboxylase.

Journal: Biochemical and biophysical research communications 20020705

Title: Clinical effects of L-threo-3,4-dihydroxyphenylserine on orthostatic hypotension in hemodialysis patients.

Journal: Nephron 20020401

Title: Efficacy of high sodium intake in a boy with instantaneous orthostatic hypotension.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20020201

Title: Effects of L-threo-3,4-dihydroxyphenylserine on orthostatic hypotension in hemodialysis patients.

Journal: American journal of nephrology 20020101

Title: The norepinephrine precursor L-threo-3,4-dihydroxyphenylserine facilitates motor recovery in chronic stroke patients.

Journal: Journal of clinical neuroscience : official journal of the Neurosurgical Society of Australasia 20011101

Title: L-threo-dihydroxyphenylserine (L-threo-DOPS; droxidopa) in the management of neurogenic orthostatic hypotension: a multi-national, multi-center, dose-ranging study in multiple system atrophy and pure autonomic failure.

Journal: Clinical autonomic research : official journal of the Clinical Autonomic Research Society 20010801

Title: Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine as potential in vivo precursors of fluorinated norepinephrines.

Journal: The Journal of organic chemistry 20010713

Title: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters.

Journal: The Journal of biological chemistry 20010518

Title: Amelioration of frozen gait by tandospirone, a serotonin 1A agonist, in a patient with pure akinesia developing resistance to L-threo-3,4-dihydroxyphenylserine.

Journal: Clinical neuropharmacology 20010101

Title: Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.

Journal: Biological & pharmaceutical bulletin 20001201

Title: [Malignant syndrome in multiple system atrophy].

Journal: No to shinkei = Brain and nerve 19970601

Title: The involvement of noradrenaline, 5-hydroxytryptamine and acetylcholine in imipramine-induced seizures in mice.

Journal: Experientia 19931015

Title: Attenuation of haloperidol-induced catalepsy by noradrenaline and L-threo-DOPS.

Journal: Journal of neural transmission. Parkinson's disease and dementia section 19930101

Title: Effect of L-threo-3,4-dihydroxyphenylserine on muscle sympathetic nerve activity in humans.

Journal: Journal of the autonomic nervous system 19920615

Title: Oxaprotiline enantiomers given repeatedly and brain alpha-adrenoceptors.

Journal: Journal of neural transmission. General section 19900101

Title: L-threo-3,4-dihydroxyphenylserine treatment for gait apraxia in parkinsonian patients.

Journal: The Kurume medical journal 19890101

Title: Effect of L-threo-3,4-dihydroxyphenylserine on muscle sympathetic nerve activities in Shy-Drager syndrome.

Journal: Neurology 19880701

Title: Alteration of lidocaine- or procaine-induced convulsions by manipulation of brain amines.

Journal: Journal of dental research 19810201

Title: [Inhibition of harmaline induced tremor by L-threo-3, 4-dihydroxyphenylserine, an L-norepinephrine precursor].

Journal: Nihon yakurigaku zasshi. Folia pharmacologica Japonica 19760401

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Tags:3916-18-5 Molecular Formula|3916-18-5 MDL|3916-18-5 SMILES|3916-18-5 (2RS,3RS)-2-AMINO-3-(3,4-DIHYDROXY-PHENYL)-3-HYDROXY-PROPIONIC ACID