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N-Arachidonyldopamine

Alias: N-Arachidonyldopamine
Cat No.:V49231 Purity: ≥98%
N-Arachidonyldopamine is a potent and specific endogenous CB1 receptor agonist (activator) with Ki of 250 nM.
N-Arachidonyldopamine
N-Arachidonyldopamine Chemical Structure CAS No.: 199875-69-9
Product category: Cannabinoid Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
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Other Forms of N-Arachidonyldopamine:

  • N-Arachidonyldopamine-d8
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
N-Arachidonyldopamine is a potent and specific endogenous CB1 receptor agonist (activator) with Ki of 250 nM. N-Arachidonyldopamine is also a potent and specific TRPV1 agonist with EC50 of ~50 nM.
N-Arachidonyldopamine (CAS 199875-69-9), also known as NADA or AA-DA, is an endogenous lipid mediator belonging to the N-acyldopamine family, formed via conjugation of arachidonic acid with dopamine. It has a molecular weight of 439.64 g/mol and formula C28H41NO3. N-Arachidonyldopamine is a potent and specific endogenous CB1 receptor agonist with a Ki of 250 nM and a potent TRPV1 agonist with an EC50 of ~50 nM.
Biological Activity I Assay Protocols (From Reference)
Targets
CB1 ( Ki = 250 nM ); TRPV1 ( EC50 ~50 nM )
N-Arachidonyldopamine targets two key receptors: cannabinoid receptor 1 (CB1) and transient receptor potential vanilloid 1 (TRPV1). It is a potent agonist at CB1 receptors with a Ki of 250 nM, showing 40-fold selectivity for CB1 over CB2 receptors (Ki = 12 µM). It is also a potent agonist at TRPV1 receptors with an EC50 of ~50 nM. The compound has no action at dopamine receptors.
ln Vitro
N-Arachidonyldopamine is a potent endogenous CB1 receptor agonist with a Ki of 250 nM, showing 40-fold selectivity for CB1 over CB2 receptors. It is also a potent TRPV1 agonist with an EC50 of ~50 nM. The compound has no action at dopamine receptors. As an endogenous lipid signaling molecule, it plays multifaceted roles in mammalian physiology, including inflammation and neuroscience research.
ln Vivo
In vivo, N-arachidonyldopamine is an endogenous lipid signaling molecule that plays multifaceted roles in mammalian physiology. As a dual CB1/TRPV1 agonist, it is involved in pain modulation, inflammation, and other physiological processes. The compound is not used as a therapeutic agent but is studied for its roles in neuroscience and inflammation research. Specific in vivo efficacy studies for therapeutic applications are not documented.
Enzyme Assay
The in vitro receptor binding assay for N-arachidonyldopamine typically involves measuring its affinity for CB1 and TRPV1 receptors. For CB1 binding, membrane preparations from rat brain are incubated with varying concentrations of N-arachidonyldopamine (typically 0.001-100 µM) and a radiolabeled ligand such as [3H]CP-55940. The binding affinity (Ki = 250 nM for CB1) is determined by competition binding analysis. For TRPV1 activity, calcium flux assays are performed using TRPV1-expressing cells.
Cell Assay
In vitro cellular assays for N-arachidonyldopamine typically involve treating cells expressing CB1 or TRPV1 receptors with the compound at concentrations ranging from 0.001 to 10 µM. CB1 receptor activation is assessed by measuring cAMP production (inhibition of forskolin-stimulated cAMP). TRPV1 activation is assessed by measuring calcium influx using fluorescent calcium indicators. The compound is dissolved in DMSO and diluted in cell culture medium.
Animal Protocol
In vivo animal studies for N-arachidonyldopamine are not typically performed for therapeutic purposes, as the compound is an endogenous lipid mediator. The compound may be used in pharmacological studies to investigate the roles of CB1 and TRPV1 receptors in pain, inflammation, and other physiological processes. The compound is administered to animals via injection, and behavioral and physiological responses are measured.
ADME/Pharmacokinetics
N-Arachidonyldopamine has a molecular weight of 439.64 g/mol and formula C28H41NO3. It is an endogenous lipid mediator. The compound is soluble in organic solvents such as DMSO and ethanol. Recommended storage is at -20°C. Detailed PK parameters such as half-life, Cmax, AUC, and bioavailability would require experimental determination. The compound is also known as NADA and AA-DA.
Toxicity/Toxicokinetics
N-Arachidonyldopamine is intended for research use only and is not approved for human therapeutic applications. As an endogenous compound, it is generally considered to have low toxicity, but appropriate safety precautions should be taken when handling. Standard toxicity assessments would include acute toxicity and repeated-dose toxicity studies if required for specific applications. The compound is a dual CB1/TRPV1 agonist and may have physiological effects at high concentrations.
References

[1]. N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J. 2000 Nov 1;351 Pt 3(Pt 3):817-24.

[2]. An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proc Natl Acad Sci U S A. 2002 Jun 11;99(12):8400-5.

Additional Infomation
Arachidonoyl dopamine is a fatty amide, belonging to the catechol class of compounds. It is a secondary carboxylamide and also an N-(fatty acyl)-dopamine. Functionally, it is related to dopamine and arachidonic acid.
N-Arachidonyldopamine (CAS 199875-69-9) is an endogenous lipid mediator belonging to the N-acyldopamine family with a molecular weight of 439.64 g/mol and formula C28H41NO3. It is a potent CB1 receptor agonist (Ki = 250 nM, 40-fold selective over CB2) and a potent TRPV1 agonist (EC50 ~50 nM). The compound has no action at dopamine receptors. It is also known as NADA and AA-DA. The compound is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H41NO3
Molecular Weight
439.63004
Exact Mass
439.308
Elemental Analysis
C, 76.50; H, 9.40; N, 3.19; O, 10.92
CAS #
199875-69-9
Related CAS #
N-Arachidonyldopamine-d8; 1159908-42-5
PubChem CID
5282105
Appearance
Solid powder
Density
1.0±0.1 g/cm3
Boiling Point
640.0±55.0 °C at 760 mmHg
Flash Point
340.8±31.5 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.546
LogP
7.07
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
17
Heavy Atom Count
32
Complexity
579
Defined Atom Stereocenter Count
0
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCC1=CC(O)=C(O)C=C1)=O
InChi Key
MVVPIAAVGAWJNQ-DOFZRALJSA-N
InChi Code
InChI=1S/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15-
Chemical Name
(5Z,8Z,11Z,14Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
Synonyms
N-Arachidonyldopamine
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 Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2746 mL 11.3732 mL 22.7464 mL
5 mM 0.4549 mL 2.2746 mL 4.5493 mL
10 mM 0.2275 mL 1.1373 mL 2.2746 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

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