Levodopa

Dopamine precursor CAS# 59-92-7

Levodopa

Catalog No. BCN1098----Order now to get a substantial discount!

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Chemical structure

Levodopa

3D structure

Chemical Properties of Levodopa

Cas No. 59-92-7 SDF Download SDF
PubChem ID 6047 Appearance White powder
Formula C9H11NO4 M.Wt 197.20
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms Levodopa
Solubility H2O : 2 mg/mL (10.14 mM; Need ultrasonic and warming)
Chemical Name (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
SMILES C1=CC(=C(C=C1CC(C(=O)O)N)O)O
Standard InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
Standard InChI InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Levodopa

The seeds of Mucuna sempervirens Hemsl.

Biological Activity of Levodopa

DescriptionLevodopa is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), used to treat Parkinson's symptoms.
TargetsDopamine D3
In vitro

Evaluation of the Cytotoxicity of Levodopa and its Complex with Hydroxypropyl-ß-Cyclodextrin (HP-ß-CD) to an Astrocyte Cell Line.[Pubmed: 25941458]

Malays J Med Sci. 2014 Dec;21(Spec Issue):6-11.


METHODS AND RESULTS:
A simple, reliable a 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxy-phenyl)-2-(4-sulfophenyl)-2H-tetrazolium, (MTS) assay was conducted to evaluate the potential cytotoxic effects of Levodopa, a "gold standard therapy" for Parkinsonism, and its complex with Hydroxypropyl-β-Cyclodextrin (HP-β-CD) on an astrocyte cell line. The cells were incubated in a range of concentrations from 4.69 to 300 μg/mL Levodopa, HP-β-CD or the complex for up to 72 hours. At every 24-hour interval, the optical density (OD), which reflects the number of viable cells, was recorded. In general, linear dose-dependent cytotoxicity profiles were observed for the cells subjected to Levodopa or the complex, whereas a slightly triphasic response was observed for the cells exposed to HP-β-CD. A significant difference (P < 0.05) in cytotoxicity was detected between the HP-β-CD-treated group and the Levodopa-treated group.
CONCLUSIONS:
In particular, we observed that the cells treated with the complex, even at the highest concentrations (> 200 μg/mL), exhibited improved tolerability in a time-dependent manner, which may indicate the potential ability of HP-β-CD to mask the toxic effects of Levodopa via complexation.

In vivo

[Effects of a single dose levodopa on heart rate variability in Parkinson's disease].[Pubmed: 25916922]

Zhonghua Yi Xue Za Zhi. 2015 Feb 17;95(7):493-5.

To explore the effects of Levodopa on heart rate variability (HRV) in Parkinson's disease (PD).
METHODS AND RESULTS:
A total of 48 PD patients (M:F = 35: 13, mean age: 59 ± 6 years, duration of illness: 4.7 ± 1.8 years, Hoehn & Yahr stage: 2.2 ± 0.3) on a stable dose of Levodopa were recruited from January 2012 to May 2014.For confirming autonomic dysfunction, the baseline patient data (12 hours off-medication) were compared with a control group consisting of 48 age and gender-matched healthy subjects (M: F = 35: 13, mean age 58 ± 6 years). Resting lead II electrocardiogram (ECG) was recorded at baseline and continuously after two tablets of 100/10 mg Levodopa/carbidopa.However, 5-min segments were selected from every quarter, i.e., Q1 (0-15 min), Q2 (15-30 min), Q3 (30-45 min) and Q4 (45-60 min). Artifact-free 5-min segments of ECG were analyzed offline to acquire the parameters of heart rate variability in time and frequency domains. At baseline, PD patients had a significantly reduced standard deviation of normal-to-normal intervals (SDRR) [(24 ± 4) vs (26 ± 4) ms, P < 0.01)] and total power (TP) [(569 ± 180) vs (652 ± 205) ms2, P < 0.05] when compared to controls. Comparing of HRV in PD patients at baseline and during first hour after drug administration, we observed significant increase in SDRR [(29 ± 12) vs (24 ± 8) ms, P < 0.05)], TP [(708 ± 253) vs (569 ± 180) ms2, P < 0.01], low frequency power (LF) [(203 ± 98) vs (168 ± 60) ms2, P < 0.05) ] and high frequency power (HF) [158 ± 86) vs (114 ± 90) ms2, P < 0.05] in Q3.
CONCLUSIONS:
The results suggest an improvement in the overall variability of heart rate resulting from an enhanced vagal tone.

Protocol of Levodopa

Animal Research

Coadministration of hydroxysafflor yellow A with levodopa attenuates the dyskinesia.[Pubmed: 25914172]

Physiol Behav. 2015 Apr 23;147:193-197.

Levodopa (L-DOPA) is used as the most effective drug available for the symptomatic treatment of Parkinson's disease (PD). However, long-term treatment of Levodopa frequently causes complications, including abnormal involuntary movements such as dyskinesia and response fluctuations in PD patients.
METHODS AND RESULTS:
In the present work, we investigated whether hydroxysafflor yellow A (HSYA) ameliorates Levodopa-induced dyskinesia and motor fluctuations in the 6-hydroxydopamine-lesioned rat model of PD. Valid PD rats were treated daily with vehicle, HSYA alone, Levodopa, or a combination of HSYA plus Levodopa for 21days, respectively.Levodopa(8mg/kg) and benserazide (15mg/kg) were treated intraperitoneally. HSYA was administrated intraperitoneally at a dose of 10mg/kg. The abnormal involuntary movements and rotational behavior were evaluated. The expression of the dopamine D3 receptor in the striatum was also assayed. The results demonstrated that daily administration of Levodopa to PD rats for 21days induced a steady expression of dyskinesia. Coadministration of HSYA with Levodopa significantly ameliorated Levodopa-induced dyskinesia. The combination treatment also prevented the shortening of the motor response duration that defines wearing off motor fluctuations. HSYA also inhibited the increase of expression of the dopamine D3 receptor in the striatum.
CONCLUSIONS:
These findings demonstrated that HSYA provided anti-dyskinetic relief against Levodopa in a preclinical model of PD via regulating the expression of the dopamine D3 receptor. The combination of Levodopa and HSYA also reduced the likelihood of wearing off development, and may thus support the utility of such compounds for the improved treatment of PD.

Levodopa Dilution Calculator

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Preparing Stock Solutions of Levodopa

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.071 mL 25.355 mL 50.7099 mL 101.4199 mL 126.7748 mL
5 mM 1.0142 mL 5.071 mL 10.142 mL 20.284 mL 25.355 mL
10 mM 0.5071 mL 2.5355 mL 5.071 mL 10.142 mL 12.6775 mL
50 mM 0.1014 mL 0.5071 mL 1.0142 mL 2.0284 mL 2.5355 mL
100 mM 0.0507 mL 0.2535 mL 0.5071 mL 1.0142 mL 1.2677 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Levodopa

Each tablet also contains corn starch, magnesium stearate, microcrystalline cellulose, povidone, talc and D&C Red No.7 lake dye.

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References on Levodopa

Evaluation of the Cytotoxicity of Levodopa and its Complex with Hydroxypropyl-ss-Cyclodextrin (HP-ss-CD) to an Astrocyte Cell Line.[Pubmed:25941458]

Malays J Med Sci. 2014 Dec;21(Spec Issue):6-11.

A simple, reliable a 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxy-phenyl)-2-(4-sulfophenyl)-2H-tet razolium, (MTS) assay was conducted to evaluate the potential cytotoxic effects of Levodopa, a "gold standard therapy" for Parkinsonism, and its complex with Hydroxypropyl-beta-Cyclodextrin (HP-beta-CD) on an astrocyte cell line. The cells were incubated in a range of concentrations from 4.69 to 300 mug/mL Levodopa, HP-beta-CD or the complex for up to 72 hours. At every 24-hour interval, the optical density (OD), which reflects the number of viable cells, was recorded. In general, linear dose-dependent cytotoxicity profiles were observed for the cells subjected to Levodopa or the complex, whereas a slightly triphasic response was observed for the cells exposed to HP-beta-CD. A significant difference (P < 0.05) in cytotoxicity was detected between the HP-beta-CD-treated group and the Levodopa-treated group. In particular, we observed that the cells treated with the complex, even at the highest concentrations (> 200 mug/mL), exhibited improved tolerability in a time-dependent manner, which may indicate the potential ability of HP-beta-CD to mask the toxic effects of Levodopa via complexation.

Levodopa enhances explicit new-word learning in healthy adults: a preliminary study.[Pubmed:25900350]

Hum Psychopharmacol. 2015 Sep;30(5):341-9.

OBJECTIVE: While the role of dopamine in modulating executive function, working memory and associative learning has been established; its role in word learning and language processing more generally is not clear. This preliminary study investigated the impact of increased synaptic dopamine levels on new-word learning ability in healthy young adults using an explicit learning paradigm. METHOD: A double-blind, placebo-controlled, between-groups design was used. Participants completed five learning sessions over 1 week with Levodopa or placebo administered at each session (five doses, 100 mg). Each session involved a study phase followed by a test phase. Test phases involved recall and recognition tests of the new (non-word) names previously paired with unfamiliar objects (half with semantic descriptions) during the study phase. RESULTS: The Levodopa group showed superior recall accuracy for new words over five learning sessions compared with the placebo group and better recognition accuracy at a 1-month follow-up for words learnt with a semantic description. CONCLUSIONS: These findings suggest that dopamine boosts initial lexical acquisition and enhances longer-term consolidation of words learnt with semantic information, consistent with dopaminergic enhancement of semantic salience.

Coadministration of hydroxysafflor yellow A with levodopa attenuates the dyskinesia.[Pubmed:25914172]

Physiol Behav. 2015 Aug 1;147:193-7.

Levodopa (L-DOPA) is used as the most effective drug available for the symptomatic treatment of Parkinson's disease (PD). However, long-term treatment of L-DOPA frequently causes complications, including abnormal involuntary movements such as dyskinesia and response fluctuations in PD patients. In the present work, we investigated whether hydroxysafflor yellow A (HSYA) ameliorates L-DOPA-induced dyskinesia and motor fluctuations in the 6-hydroxydopamine-lesioned rat model of PD. Valid PD rats were treated daily with vehicle, HSYA alone, L-DOPA, or a combination of HSYA plus L-DOPA for 21days, respectively. L-DOPA (8mg/kg) and benserazide (15mg/kg) were treated intraperitoneally. HSYA was administrated intraperitoneally at a dose of 10mg/kg. The abnormal involuntary movements and rotational behavior were evaluated. The expression of the dopamine D3 receptor in the striatum was also assayed. The results demonstrated that daily administration of L-DOPA to PD rats for 21days induced a steady expression of dyskinesia. Coadministration of HSYA with L-DOPA significantly ameliorated L-DOPA-induced dyskinesia. The combination treatment also prevented the shortening of the motor response duration that defines wearing off motor fluctuations. HSYA also inhibited the increase of expression of the dopamine D3 receptor in the striatum. These findings demonstrated that HSYA provided anti-dyskinetic relief against L-DOPA in a preclinical model of PD via regulating the expression of the dopamine D3 receptor. The combination of L-DOPA and HSYA also reduced the likelihood of wearing off development, and may thus support the utility of such compounds for the improved treatment of PD.

[Effects of a single dose levodopa on heart rate variability in Parkinson's disease].[Pubmed:25916922]

Zhonghua Yi Xue Za Zhi. 2015 Feb 17;95(7):493-5.

OBJECTIVE: To explore the effects of Levodopa on heart rate variability (HRV) in Parkinson's disease (PD). METHODS: A total of 48 PD patients (M:F = 35: 13, mean age: 59 +/- 6 years, duration of illness: 4.7 +/- 1.8 years, Hoehn & Yahr stage: 2.2 +/- 0.3) on a stable dose of Levodopa were recruited from January 2012 to May 2014.For confirming autonomic dysfunction, the baseline patient data (12 hours off-medication) were compared with a control group consisting of 48 age and gender-matched healthy subjects (M: F = 35: 13, mean age 58 +/- 6 years). Resting lead II electrocardiogram (ECG) was recorded at baseline and continuously after two tablets of 100/10 mg Levodopa/carbidopa.However, 5-min segments were selected from every quarter, i.e., Q1 (0-15 min), Q2 (15-30 min), Q3 (30-45 min) and Q4 (45-60 min). Artifact-free 5-min segments of ECG were analyzed offline to acquire the parameters of heart rate variability in time and frequency domains. RESULTS: At baseline, PD patients had a significantly reduced standard deviation of normal-to-normal intervals (SDRR) [(24 +/- 4) vs (26 +/- 4) ms, P < 0.01)] and total power (TP) [(569 +/- 180) vs (652 +/- 205) ms(2), P < 0.05] when compared to controls. Comparing of HRV in PD patients at baseline and during first hour after drug administration, we observed significant increase in SDRR [(29 +/- 12) vs (24 +/- 8) ms, P < 0.05)], TP [(708 +/- 253) vs (569 +/- 180) ms(2), P < 0.01], low frequency power (LF) [(203 +/- 98) vs (168 +/- 60) ms(2), P < 0.05) ] and high frequency power (HF) [158 +/- 86) vs (114 +/- 90) ms(2), P < 0.05] in Q3. CONCLUSION: The results suggest an improvement in the overall variability of heart rate resulting from an enhanced vagal tone.

Description

L-DOPA (Levodopa) is an orally active metabolic precursor of neurotransmitters dopamine. L-DOPA can cross the blood-brain barrier and is converted into dopamine in the brain. L-DOPA has anti-allodynic effects and the potential for Parkinson's disease.

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