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MedKoo Cat#: 111540 | Name: Arachidonyl Dopamine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arachidonyl dopamine is an endogenous lipid amide formed from arachidonic acid and dopamine, structurally related to both anandamide and capsaicin-like compounds. It exhibits bioactivity as a potent TRPV1 agonist, inducing calcium influx and contributing to pain modulation, vasodilation, and neurogenic inflammation. Additionally, it acts as a partial agonist at CB1 cannabinoid receptors, implicating it in neuromodulatory processes such as analgesia, thermoregulation, and synaptic transmission.

Chemical Structure

Arachidonyl Dopamine
Arachidonyl Dopamine
CAS#199875-69-9

Theoretical Analysis

MedKoo Cat#: 111540

Name: Arachidonyl Dopamine

CAS#: 199875-69-9

Chemical Formula: C28H41NO3

Exact Mass: 439.3086

Molecular Weight: 439.64

Elemental Analysis: C, 76.50; H, 9.40; N, 3.19; O, 10.92

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
200mg USD 1,950.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 4,650.00 2 Weeks
2g USD 6,750.00 2 Weeks
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Related CAS #
199875-69-9
Synonym
N-Arachidonoyldopamine; N-Arachidonyldopamine; NADA dopamine, arachidonyl-dopamine; arachidonyldopamine
IUPAC/Chemical Name
(5Z,8Z,11Z,14Z)-N-(3,4-dihydroxyphenethyl)icosa-5,8,11,14-tetraenamide
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-
SMILES Code
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCC1=CC=C(O)C(O)=C1)=O
Appearance
Liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
1: Sukhanova IA, Sebentsova EA, Khukhareva DD, Vysokikh MY, Bezuglov VV, Bobrov MY, Levitskaya NG. Early-life N-arachidonoyl-dopamine exposure increases antioxidant capacity of the brain tissues and reduces functional deficits after neonatal hypoxia in rats. Int J Dev Neurosci. 2019 Nov;78:7-18. doi: 10.1016/j.ijdevneu.2019.06.007. Epub 2019 Jul 29. PMID: 31369794. 2: Muller C, Morales P, Reggio PH. Cannabinoid Ligands Targeting TRP Channels. Front Mol Neurosci. 2019 Jan 15;11:487. doi: 10.3389/fnmol.2018.00487. PMID: 30697147; PMCID: PMC6340993. 3: Matsumoto G, Inobe T, Amano T, Murai K, Nukina N, Mori N. N-Acyldopamine induces aggresome formation without proteasome inhibition and enhances protein aggregation via p62/SQSTM1 expression. Sci Rep. 2018 Jun 25;8(1):9585. doi: 10.1038/s41598-018-27872-6. PMID: 29941919; PMCID: PMC6018635. 4: Novosadova EV, Arsenyeva EL, Manuilova ES, Khaspekov LG, Bobrov MY, Bezuglov VV, Illarioshkin SN, Grivennikov IA. Neuroprotective Properties of Endocannabinoids N-Arachidonoyl Dopamine and N-Docosahexaenoyl Dopamine Examined in Neuronal Precursors Derived from Human Pluripotent Stem Cells. Biochemistry (Mosc). 2017 Nov;82(11):1367-1372. doi: 10.1134/S0006297917110141. PMID: 29223163. 5: Lawton SK, Xu F, Tran A, Wong E, Prakash A, Schumacher M, Hellman J, Wilhelmsen K. N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1. J Immunol. 2017 Aug 15;199(4):1465-1475. doi: 10.4049/jimmunol.1602151. Epub 2017 Jul 12. PMID: 28701511; PMCID: PMC5544930. 6: Dux M, Deák É, Tassi N, Sántha P, Jancsó G. Endovanilloids are potential activators of the trigeminovascular nocisensor complex. J Headache Pain. 2016;17:53. doi: 10.1186/s10194-016-0644-7. Epub 2016 May 17. PMID: 27189587; PMCID: PMC4870586. 7: Redmond WJ, Cawston EE, Grimsey NL, Stuart J, Edington AR, Glass M, Connor M. Identification of N-arachidonoyl dopamine as a highly biased ligand at cannabinoid CB1 receptors. Br J Pharmacol. 2016 Jan;173(1):115-27. doi: 10.1111/bph.13341. Epub 2015 Nov 17. PMID: 26398720; PMCID: PMC4813372. 8: Almaghrabi SY, Geraghty DP, Ahuja KD, Adams MJ. Vanilloid-like agents inhibit aggregation of human platelets. Thromb Res. 2014 Aug;134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. Epub 2014 Jun 6. PMID: 24953906. 9: Fawley JA, Hofmann ME, Andresen MC. Cannabinoid 1 and transient receptor potential vanilloid 1 receptors discretely modulate evoked glutamate separately from spontaneous glutamate transmission. J Neurosci. 2014 Jun 11;34(24):8324-32. doi: 10.1523/JNEUROSCI.0315-14.2014. PMID: 24920635; PMCID: PMC4051980. 10: Ji D, Jang CG, Lee S. A sensitive and accurate quantitative method to determine N-arachidonoyldopamine and N-oleoyldopamine in the mouse striatum using column-switching LC-MS-MS: use of a surrogate matrix to quantify endogenous compounds. Anal Bioanal Chem. 2014 Jul;406(18):4491-9. doi: 10.1007/s00216-014-7816-6. Epub 2014 May 11. PMID: 24817351. 11: Vedunova MV, Mitroshina EV, Sakharnova TA, Bobrov MY, Bezuglov VV, Khaspekov LG, Mukhina IV. Effect of N-arachidonoyl dopamine on activity of neuronal network in primary hippocampus culture upon hypoxia modelling. Bull Exp Biol Med. 2014 Feb;156(4):461-4. doi: 10.1007/s10517-014-2374-7. Epub 2014 Mar 5. PMID: 24771427. 12: Wilhelmsen K, Khakpour S, Tran A, Sheehan K, Schumacher M, Xu F, Hellman J. The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells. J Biol Chem. 2014 May 9;289(19):13079-100. doi: 10.1074/jbc.M113.536953. Epub 2014 Mar 18. PMID: 24644287; PMCID: PMC4036321. 13: Freestone PS, Guatteo E, Piscitelli F, di Marzo V, Lipski J, Mercuri NB. Glutamate spillover drives endocannabinoid production and inhibits GABAergic transmission in the Substantia Nigra pars compacta. Neuropharmacology. 2014 Apr;79:467-75. doi: 10.1016/j.neuropharm.2013.12.007. Epub 2013 Dec 12. PMID: 24334069. 14: Cazade M, Nuss CE, Bidaud I, Renger JJ, Uebele VN, Lory P, Chemin J. Cross- modulation and molecular interaction at the Cav3.3 protein between the endogenous lipids and the T-type calcium channel antagonist TTA-A2. Mol Pharmacol. 2014 Feb;85(2):218-25. doi: 10.1124/mol.113.089581. Epub 2013 Nov 8. PMID: 24214826. 15: Köles L, Garção P, Zádori ZS, Ferreira SG, Pinheiro BS, da Silva-Santos CS, Ledent C, Köfalvi A. Presynaptic TRPV1 vanilloid receptor function is age- but not CB1 cannabinoid receptor-dependent in the rodent forebrain. Brain Res Bull. 2013 Aug;97:126-35. doi: 10.1016/j.brainresbull.2013.06.007. Epub 2013 Jul 4. PMID: 23831917. 16: Stock K, Kumar J, Synowitz M, Petrosino S, Imperatore R, Smith ES, Wend P, Purfürst B, Nuber UA, Gurok U, Matyash V, Wälzlein JH, Chirasani SR, Dittmar G, Cravatt BF, Momma S, Lewin GR, Ligresti A, De Petrocellis L, Cristino L, Di Marzo V, Kettenmann H, Glass R. Neural precursor cells induce cell death of high-grade astrocytomas through stimulation of TRPV1. Nat Med. 2012 Aug;18(8):1232-8. doi: 10.1038/nm.2827. Epub 2012 Jul 22. PMID: 22820645; PMCID: PMC3480991. 17: Mahmmoud YA, Gaster M. Uncoupling of sarcoplasmic reticulum Ca²⁺-ATPase by N-arachidonoyl dopamine. Members of the endocannabinoid family as thermogenic drugs. Br J Pharmacol. 2012 Aug;166(7):2060-9. doi: 10.1111/j.1476-5381.2012.01899.x. PMID: 22335600; PMCID: PMC3402771. 18: Wojtalla A, Herweck F, Granzow M, Klein S, Trebicka J, Huss S, Lerner R, Lutz B, Schildberg FA, Knolle PA, Sauerbruch T, Singer MV, Zimmer A, Siegmund SV. The endocannabinoid N-arachidonoyl dopamine (NADA) selectively induces oxidative stress-mediated cell death in hepatic stellate cells but not in hepatocytes. Am J Physiol Gastrointest Liver Physiol. 2012 Apr 15;302(8):G873-87. doi: 10.1152/ajpgi.00241.2011. Epub 2012 Feb 2. PMID: 22301114. 19: Grabiec U, Koch M, Kallendrusch S, Kraft R, Hill K, Merkwitz C, Ghadban C, Lutz B, Straiker A, Dehghani F. The endocannabinoid N-arachidonoyldopamine (NADA) exerts neuroprotective effects after excitotoxic neuronal damage via cannabinoid receptor 1 (CB(1)). Neuropharmacology. 2012 Mar;62(4):1797-807. doi: 10.1016/j.neuropharm.2011.11.023. Epub 2011 Dec 13. PMID: 22186081. 20: Hayase T. Differential effects of TRPV1 receptor ligands against nicotine- induced depression-like behaviors. BMC Pharmacol. 2011 Jul 18;11:6. doi: 10.1186/1471-2210-11-6. PMID: 21767384; PMCID: PMC3155896.

Preparing Stock Solutions

The following data is based on the product molecular weight 439.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mottawea W, Yousuf B, Sultan S, Ahmed T, Yeo J, Hüttmann N, Li Y, Bouhlel NE, Hassan H, Zhang X, Minic Z, Hammami R. Multi-level analysis of gut microbiome extracellular vesicles-host interaction reveals a connection to gut-brain axis signaling. Microbiol Spectr. 2025 Feb 4;13(2):e0136824. doi: 10.1128/spectrum.01368-24. Epub 2024 Dec 19. PMID: 39699251; PMCID: PMC11792502. 2: Gamisonia AM, Yushina MN, Fedorova-Gogolina IA, Akimov MG, Eldarov CM, Pavlovich SV, Bezuglov VV, Gretskaya NM, Sukhikh GT, Bobrov MY. N-Acyl Dopamines Induce Apoptosis in Endometrial Stromal Cells from Patients with Endometriosis. Int J Mol Sci. 2021 Sep 30;22(19):10648. doi: 10.3390/ijms221910648. PMID: 34638988; PMCID: PMC8509064. 3: Novosadova E, Antonov S, Arsenyeva E, Kobylanskiy A, Vanyushina Y, Malova T, Khaspekov L, Bobrov M, Bezuglov V, Tarantul V, Illarioshkin S, Grivennikov I. Neuroprotective and neurotoxic effects of endocannabinoid-like compounds, N-arachidonoyl dopamine and N-docosahexaenoyl dopamine in differentiated cultures of induced pluripotent stem cells derived from patients with Parkinson's disease. Neurotoxicology. 2021 Jan;82:108-118. doi: 10.1016/j.neuro.2020.11.010. Epub 2020 Nov 25. PMID: 33248189. 4: Sukhanova IA, Sebentsova EA, Khukhareva DD, Vysokikh MY, Bezuglov VV, Bobrov MY, Levitskaya NG. Early-life N-arachidonoyl-dopamine exposure increases antioxidant capacity of the brain tissues and reduces functional deficits after neonatal hypoxia in rats. Int J Dev Neurosci. 2019 Nov;78:7-18. doi: 10.1016/j.ijdevneu.2019.06.007. Epub 2019 Jul 29. PMID: 31369794. 5: Muller C, Morales P, Reggio PH. Cannabinoid Ligands Targeting TRP Channels. Front Mol Neurosci. 2019 Jan 15;11:487. doi: 10.3389/fnmol.2018.00487. PMID: 30697147; PMCID: PMC6340993. 6: Matsumoto G, Inobe T, Amano T, Murai K, Nukina N, Mori N. N-Acyldopamine induces aggresome formation without proteasome inhibition and enhances protein aggregation via p62/SQSTM1 expression. Sci Rep. 2018 Jun 25;8(1):9585. doi: 10.1038/s41598-018-27872-6. PMID: 29941919; PMCID: PMC6018635. 7: Novosadova EV, Arsenyeva EL, Manuilova ES, Khaspekov LG, Bobrov MY, Bezuglov VV, Illarioshkin SN, Grivennikov IA. Neuroprotective Properties of Endocannabinoids N-Arachidonoyl Dopamine and N-Docosahexaenoyl Dopamine Examined in Neuronal Precursors Derived from Human Pluripotent Stem Cells. Biochemistry (Mosc). 2017 Nov;82(11):1367-1372. doi: 10.1134/S0006297917110141. PMID: 29223163. 8: Lawton SK, Xu F, Tran A, Wong E, Prakash A, Schumacher M, Hellman J, Wilhelmsen K. N-Arachidonoyl Dopamine Modulates Acute Systemic Inflammation via Nonhematopoietic TRPV1. J Immunol. 2017 Aug 15;199(4):1465-1475. doi: 10.4049/jimmunol.1602151. Epub 2017 Jul 12. PMID: 28701511; PMCID: PMC5544930. 9: Dux M, Deák É, Tassi N, Sántha P, Jancsó G. Endovanilloids are potential activators of the trigeminovascular nocisensor complex. J Headache Pain. 2016;17:53. doi: 10.1186/s10194-016-0644-7. Epub 2016 May 17. PMID: 27189587; PMCID: PMC4870586. 10: Redmond WJ, Cawston EE, Grimsey NL, Stuart J, Edington AR, Glass M, Connor M. Identification of N-arachidonoyl dopamine as a highly biased ligand at cannabinoid CB1 receptors. Br J Pharmacol. 2016 Jan;173(1):115-27. doi: 10.1111/bph.13341. Epub 2015 Nov 17. PMID: 26398720; PMCID: PMC4813372. 11: Almaghrabi SY, Geraghty DP, Ahuja KD, Adams MJ. Vanilloid-like agents inhibit aggregation of human platelets. Thromb Res. 2014 Aug;134(2):412-7. doi: 10.1016/j.thromres.2014.05.038. Epub 2014 Jun 6. PMID: 24953906. 12: Fawley JA, Hofmann ME, Andresen MC. Cannabinoid 1 and transient receptor potential vanilloid 1 receptors discretely modulate evoked glutamate separately from spontaneous glutamate transmission. J Neurosci. 2014 Jun 11;34(24):8324-32. doi: 10.1523/JNEUROSCI.0315-14.2014. PMID: 24920635; PMCID: PMC4051980. 13: Ji D, Jang CG, Lee S. A sensitive and accurate quantitative method to determine N-arachidonoyldopamine and N-oleoyldopamine in the mouse striatum using column-switching LC-MS-MS: use of a surrogate matrix to quantify endogenous compounds. Anal Bioanal Chem. 2014 Jul;406(18):4491-9. doi: 10.1007/s00216-014-7816-6. Epub 2014 May 11. PMID: 24817351. 14: Vedunova MV, Mitroshina EV, Sakharnova TA, Bobrov MY, Bezuglov VV, Khaspekov LG, Mukhina IV. Effect of N-arachidonoyl dopamine on activity of neuronal network in primary hippocampus culture upon hypoxia modelling. Bull Exp Biol Med. 2014 Feb;156(4):461-4. doi: 10.1007/s10517-014-2374-7. Epub 2014 Mar 5. PMID: 24771427. 15: Wilhelmsen K, Khakpour S, Tran A, Sheehan K, Schumacher M, Xu F, Hellman J. The endocannabinoid/endovanilloid N-arachidonoyl dopamine (NADA) and synthetic cannabinoid WIN55,212-2 abate the inflammatory activation of human endothelial cells. J Biol Chem. 2014 May 9;289(19):13079-100. doi: 10.1074/jbc.M113.536953. Epub 2014 Mar 18. PMID: 24644287; PMCID: PMC4036321. 16: Freestone PS, Guatteo E, Piscitelli F, di Marzo V, Lipski J, Mercuri NB. Glutamate spillover drives endocannabinoid production and inhibits GABAergic transmission in the Substantia Nigra pars compacta. Neuropharmacology. 2014 Apr;79:467-75. doi: 10.1016/j.neuropharm.2013.12.007. Epub 2013 Dec 12. PMID: 24334069. 17: Cazade M, Nuss CE, Bidaud I, Renger JJ, Uebele VN, Lory P, Chemin J. Cross- modulation and molecular interaction at the Cav3.3 protein between the endogenous lipids and the T-type calcium channel antagonist TTA-A2. Mol Pharmacol. 2014 Feb;85(2):218-25. doi: 10.1124/mol.113.089581. Epub 2013 Nov 8. PMID: 24214826. 18: Köles L, Garção P, Zádori ZS, Ferreira SG, Pinheiro BS, da Silva-Santos CS, Ledent C, Köfalvi A. Presynaptic TRPV1 vanilloid receptor function is age- but not CB1 cannabinoid receptor-dependent in the rodent forebrain. Brain Res Bull. 2013 Aug;97:126-35. doi: 10.1016/j.brainresbull.2013.06.007. Epub 2013 Jul 4. PMID: 23831917. 19: Stock K, Kumar J, Synowitz M, Petrosino S, Imperatore R, Smith ES, Wend P, Purfürst B, Nuber UA, Gurok U, Matyash V, Wälzlein JH, Chirasani SR, Dittmar G, Cravatt BF, Momma S, Lewin GR, Ligresti A, De Petrocellis L, Cristino L, Di Marzo V, Kettenmann H, Glass R. Neural precursor cells induce cell death of high-grade astrocytomas through stimulation of TRPV1. Nat Med. 2012 Aug;18(8):1232-8. doi: 10.1038/nm.2827. Epub 2012 Jul 22. PMID: 22820645; PMCID: PMC3480991. 20: Mahmmoud YA, Gaster M. Uncoupling of sarcoplasmic reticulum Ca²⁺-ATPase by N-arachidonoyl dopamine. Members of the endocannabinoid family as thermogenic drugs. Br J Pharmacol. 2012 Aug;166(7):2060-9. doi: 10.1111/j.1476-5381.2012.01899.x. PMID: 22335600; PMCID: PMC3402771.