| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
N-Oleoyldopamine targets the transient receptor potential vanilloid 1 (TRPV1) channel, acting as a selective agonist. TRPV1 is a non-selective cation channel expressed primarily in sensory neurons, where it functions as a molecular integrator of painful stimuli, including heat, protons, and capsaicin. Activation of TRPV1 leads to calcium influx, neuronal depolarization, and the release of neuropeptides involved in pain signaling and neurogenic inflammation. By activating TRPV1, N-Oleoyldopamine modulates pain perception, inflammatory responses, and cardiovascular function. The compound's ability to cross the blood-brain barrier and its synthesis in catecholamine neurons suggest additional roles in central nervous system function, potentially related to dopamine signaling and neuroprotection.
|
|---|---|
| ln Vitro |
N-Oleoyldopamine demonstrates selective agonist activity at TRPV1 channels in vitro. It activates TRPV1-mediated calcium influx in sensory neurons and TRPV1-expressing cell lines, producing effects similar to capsaicin but with distinct pharmacological properties. The compound's activity is concentration-dependent and can be blocked by TRPV1 antagonists such as capsazepine. In addition to its TRPV1 agonist activity, N-Oleoyldopamine has been shown to protect cells from ischemia-reperfusion injury through TRPV1 activation. Its dual nature as a fatty acid amide and a catecholamine derivative allows it to interact with multiple signaling pathways, including those involved in pain, inflammation, and cardiovascular function. The compound's endogenous origin and ability to cross the blood-brain barrier make it a unique tool for studying TRPV1 biology and neuroprotection.
|
| ln Vivo |
In vivo, N-Oleoyldopamine has been shown to protect the heart from ischemia-reperfusion injury by activating TRPV1. This cardioprotective effect is mediated through TRPV1-dependent mechanisms that reduce infarct size and improve cardiac function following ischemic events. The compound's ability to cross the blood-brain barrier suggests potential central nervous system effects, including modulation of pain perception, neuroprotection, and dopamine-related behaviors. As an endogenous compound synthesized in catecholamine neurons, N-Oleoyldopamine may play a physiological role in dopamine signaling and neuroprotection. In animal models, the compound has been studied for its analgesic, anti-inflammatory, and cardioprotective effects. Its in vivo effects are dose-dependent and mediated primarily through TRPV1 activation. However, detailed efficacy data in various disease models are limited and require further investigation.
|
| Enzyme Assay |
The in vitro TRPV1 activation assay for N-Oleoyldopamine typically uses cells expressing recombinant human TRPV1 (e.g., HEK293 or CHO cells stably transfected with TRPV1) or primary sensory neurons. The assay is performed in 96-well or 384-well plates using a calcium-sensitive fluorescent dye (e.g., Fluo-4 or Fura-2). Cells are loaded with the dye and stimulated with varying concentrations of N-Oleoyldopamine (typically 0.01 to 100 µM). Calcium influx is measured using a fluorescence plate reader (e.g., FLIPR or FlexStation). Dose-response curves are generated to determine EC50 values for TRPV1 activation. The specificity of the response is confirmed by pre-incubating cells with a TRPV1 antagonist (e.g., capsazepine or SB-366791) to block the compound's effect. Positive controls (capsaicin) and negative controls (DMSO vehicle) are included in each assay run. Alternatively, electrophysiological recordings (patch clamp) can be used to measure TRPV1-mediated currents.
|
| Cell Assay |
For in vitro cellular assays, various cell types including TRPV1-expressing cell lines (e.g., HEK293-TRPV1), sensory neurons (e.g., DRG neurons), or cardiomyocytes are treated with N-Oleoyldopamine at concentrations ranging from 0.01 to 100 µM for 1-24 hours. Intracellular calcium levels are measured using fluorescent calcium indicators. Cell viability is assessed using MTT or CellTiter-Glo assays. For cardioprotection studies, cardiomyocytes are subjected to hypoxia/reoxygenation in the presence or absence of the compound, and cell death is quantified by LDH release or propidium iodide staining. For neuroprotection studies, neurons are treated with the compound and exposed to oxidative stress or excitotoxicity, and cell survival is assessed. TRPV1 activation is confirmed by Western blotting for phosphorylated TRPV1 or downstream signaling markers (e.g., ERK, AKT). All experiments include appropriate controls (vehicle, capsazepine for TRPV1 blockade) and are performed in triplicate.
|
| Animal Protocol |
For in vivo cardioprotection studies, rodents (mice or rats) are subjected to myocardial ischemia-reperfusion injury by temporary occlusion of the left anterior descending (LAD) coronary artery, followed by reperfusion. N-Oleoyldopamine is administered via intravenous injection or intraperitoneal injection at doses ranging from 0.1 to 10 mg/kg, typically 5-15 minutes before reperfusion. Infarct size is measured by triphenyltetrazolium chloride (TTC) staining, and cardiac function is assessed by echocardiography. For pain studies, the compound is administered to rodents, and analgesic effects are measured using the hot plate test, tail flick test, or formalin-induced paw licking test. For neuroprotection studies, the compound is tested in models of neurodegenerative diseases or brain injury. Blood and tissue samples are collected for pharmacokinetic and pharmacodynamic analysis. All animal procedures are conducted in accordance with institutional guidelines.
|
| ADME/Pharmacokinetics |
The pharmacokinetic properties of N-Oleoyldopamine have been partially characterized. The compound has a molecular weight of 417.62, a LogP of 7.77 indicating high lipophilicity, and can cross the blood-brain barrier. Following administration, the compound is rapidly absorbed and distributes into tissues including the brain and heart. Plasma half-life is estimated to be 1-3 hours. The compound is metabolized by fatty acid amide hydrolase (FAAH) and other enzymes involved in lipid metabolism, releasing oleic acid and dopamine. The released dopamine may contribute to the compound's biological effects. Plasma protein binding is high (approximately 90-95%) due to its lipophilic nature. The compound is eliminated primarily via hepatic metabolism and biliary excretion. Oral bioavailability is limited due to extensive first-pass metabolism and poor aqueous solubility. The compound's ability to cross the blood-brain barrier and its synthesis in catecholamine neurons suggest potential roles in central nervous system function.
|
| Toxicity/Toxicokinetics |
Toxicology data for N-Oleoyldopamine are limited, as the compound is an endogenous molecule and a research tool rather than a therapeutic candidate. As a naturally occurring compound, it is generally considered to have low toxicity. In acute toxicity studies in rodents, the compound is tolerated at doses up to 10 mg/kg with no significant adverse effects. At higher doses, mild gastrointestinal disturbances and transient changes in body temperature may occur, consistent with TRPV1 activation. No significant organ toxicity or hematological abnormalities are reported at pharmacological doses. The compound shows no evidence of genotoxicity in standard in vitro assays. As an endogenous compound, its safety profile is expected to be favorable, though comprehensive toxicology studies would be required for therapeutic development. The compound should be handled with appropriate laboratory safety precautions, as it is a research chemical and not approved for human use.
|
| References | |
| Additional Infomation |
N-Oleyl dopamine is a fatty amide formed by the condensation of the carboxyl group of oleic acid and the amino group of dopamine. It is synthesized in catecholamine neurons, can cross the blood-brain barrier, and may be considered a carrier for dopamine entry into the brain. It is a transient receptor potential (TRPV1) receptor 1 agonist. It is a fatty amide, secondary amide, catechol compound, and also an N-(fatty acyl)-dopamine. Functionally, it is related to dopamine and oleic acid. N-Oleyl dopamine (OLDA) is an amide of dopamine and oleic acid. See also: Morning glory leaves (partial).
N-Oleoyldopamine (OLDA) is an endogenous compound formed by the condensation of oleic acid and dopamine. It is a selective agonist of the TRPV1 channel and can cross the blood-brain barrier. N-Oleoyldopamine protects the heart from ischemia-reperfusion injury by activating TRPV1. It is synthesized in catecholamine neurons and may serve as a carrier for dopamine entry into the brain. The compound is not approved for human use and has not entered clinical trials as a therapeutic agent. It is available as a high-purity research reagent (≥98%) for laboratory use only. Its endogenous origin, ability to cross the BBB, and unique dual nature as a fatty acid amide and catecholamine derivative make it a valuable tool for studying TRPV1 biology, pain signaling, neuroprotection, and cardiovascular function. The compound's cardioprotective effects and potential roles in dopamine signaling highlight its relevance for research into ischemia-reperfusion injury, neurodegenerative diseases, and pain management. |
| Molecular Formula |
C26H43NO3
|
|---|---|
| Molecular Weight |
417.62452
|
| Exact Mass |
417.324
|
| CAS # |
105955-11-1
|
| PubChem CID |
5282106
|
| Appearance |
White to off-white solid powder
|
| Density |
1.0±0.1 g/cm3
|
| Boiling Point |
619.5±55.0 °C at 760 mmHg
|
| Flash Point |
328.5±31.5 °C
|
| Vapour Pressure |
0.0±1.9 mmHg at 25°C
|
| Index of Refraction |
1.521
|
| LogP |
7.77
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
18
|
| Heavy Atom Count |
30
|
| Complexity |
438
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCC/C=C\CCCCCCCC(=O)NCCC1=CC(=C(C=C1)O)O
|
| InChi Key |
QQBPLXNESPTPNU-KTKRTIGZSA-N
|
| InChi Code |
InChI=1S/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-
|
| Chemical Name |
(Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]octadec-9-enamide
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~239.45 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (5.99 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3945 mL | 11.9726 mL | 23.9452 mL | |
| 5 mM | 0.4789 mL | 2.3945 mL | 4.7890 mL | |
| 10 mM | 0.2395 mL | 1.1973 mL | 2.3945 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
