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MedKoo Cat#: 525001 | Name: Anandamide
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Description:

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

Anandamide, also known as N-arachidonoylethanolamine or AEA, is a fatty acid neurotransmitter derived from the non-oxidative metabolism of eicosatetraenoic acid (arachidonic acid) an essential ω-6 polyunsaturated fatty acid. The name is taken from the Sanskrit word ananda, which means "joy, bliss, delight", and amide. It is synthesized from N-arachidonoyl phosphatidylethanolamine by multiple pathways. It is degraded primarily by the fatty acid amide hydrolase (FAAH) enzyme, which converts anandamid.

Chemical Structure

Anandamide
Anandamide
CAS#94421-68-8

Theoretical Analysis

MedKoo Cat#: 525001

Name: Anandamide

CAS#: 94421-68-8

Chemical Formula: C22H35NO3

Exact Mass: 361.2617

Molecular Weight: 361.53

Elemental Analysis: C, 73.09; H, 9.76; N, 3.87; O, 13.28

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Anandamide; AEA; Arachidonylethanolamide; Arachidonoyl ethanolamide.
IUPAC/Chemical Name
N-Arachidonoyl-2-hydroxyethylamide
InChi Key
LIGWYLOEDYSMTP-DOFZRALJSA-N
InChi Code
InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(25)23-22(26)20-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-20H2,1H3,(H,23,25,26)/b7-6-,10-9-,13-12-,16-15-
SMILES Code
O=C(NC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)CO
Appearance
A solution in ethanol
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Endogenous and non-selective CB agonist.
In vitro activity:
AEA significantly inhibited TNF-α production from 2.5 μM up to 10 μM, being ineffective at lower concentrations (Supplemental Fig. 1A). Furthermore, 2.5 μM AEA did not affect cell viability, which decreased to ∼70% at 10 μM (data not shown). Upon activation with IFN-γ, HaCaT cells also produced significantly higher levels of several proinflammatory cytokines (IL-6, IL-8, TNF-α, IL-12 p40), as compared with untreated controls. When cells were pretreated with 2.5 μM AEA, the production of TNF-α and IL-12 p40 was significantly suppressed, whereas no significant effect was observed on IL-6 and IL-8 levels (Fig. 1A). Reference: J Immunol. 2016 Nov 1;197(9):3545-3553. https://pubmed.ncbi.nlm.nih.gov/27694494/
In vivo activity:
This study observed that the clinical parameters for lung function including specific airways resistance, specific airway conductance, and minute per volume to be significantly improved in SEB + AEA groups and similar to the naïve group, in comparison to SEB + VEH mice (Figure 1A). These data demonstrated that AEA was able to rescue impairments to the lung function caused by SEB exposure. Further, the total number of mononuclear cells (MNCs) in the lung was significantly decreased in SEB + AEA mice when compared to SEB + VEH mice (Figure 1B). Histological sections of the lungs are shown in Figure 1C that are representative pictures of the data presented in Figure 1B. Reference: Front Pharmacol. 2021; 12: 644281. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8113864/
Solvent mg/mL mM comments
Solubility
Ethanol:PBS (1:2) 8.5 23.51
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 361.53 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
Formulation protocol:
1. Costa L, Moreia-Pinto B, Felgueira E, Ribeiro A, Rebelo I, Fonseca BM. The major endocannabinoid anandamide (AEA) induces apoptosis of human granulosa cells. Prostaglandins Leukot Essent Fatty Acids. 2021 Jun 8;171:102311. doi: 10.1016/j.plefa.2021.102311. Epub ahead of print. PMID: 34126378. 2. Chiurchiù V, Rapino C, Talamonti E, Leuti A, Lanuti M, Gueniche A, Jourdain R, Breton L, Maccarrone M. Anandamide Suppresses Proinflammatory T Cell Responses In Vitro through Type-1 Cannabinoid Receptor-Mediated mTOR Inhibition in Human Keratinocytes. J Immunol. 2016 Nov 1;197(9):3545-3553. doi: 10.4049/jimmunol.1500546. Epub 2016 Sep 30. PMID: 27694494. 3. Çengelli Ünel Ç, Dönertaş B, Aydin Ş, Ulupinar E, Özatik O, Kaygisiz B, Yildirim E, Erol K. Protective effects of anandamide against cisplatin-induced peripheral neuropathy in rats. Turk J Med Sci. 2021 Jun 13. doi: 10.3906/sag-2101-224. Epub ahead of print. PMID: 34118805. 4. Sultan M, Alghetaa H, Mohammed A, Abdulla OA, Wisniewski PJ, Singh N, Nagarkatti P, Nagarkatti M. The Endocannabinoid Anandamide Attenuates Acute Respiratory Distress Syndrome by Downregulating miRNA that Target Inflammatory Pathways. Front Pharmacol. 2021 Apr 27;12:644281. doi: 10.3389/fphar.2021.644281. PMID: 33995054; PMCID: PMC8113864.
In vitro protocol:
1. Costa L, Moreia-Pinto B, Felgueira E, Ribeiro A, Rebelo I, Fonseca BM. The major endocannabinoid anandamide (AEA) induces apoptosis of human granulosa cells. Prostaglandins Leukot Essent Fatty Acids. 2021 Jun 8;171:102311. doi: 10.1016/j.plefa.2021.102311. Epub ahead of print. PMID: 34126378. 2. Chiurchiù V, Rapino C, Talamonti E, Leuti A, Lanuti M, Gueniche A, Jourdain R, Breton L, Maccarrone M. Anandamide Suppresses Proinflammatory T Cell Responses In Vitro through Type-1 Cannabinoid Receptor-Mediated mTOR Inhibition in Human Keratinocytes. J Immunol. 2016 Nov 1;197(9):3545-3553. doi: 10.4049/jimmunol.1500546. Epub 2016 Sep 30. PMID: 27694494.
In vivo protocol:
1. Çengelli Ünel Ç, Dönertaş B, Aydin Ş, Ulupinar E, Özatik O, Kaygisiz B, Yildirim E, Erol K. Protective effects of anandamide against cisplatin-induced peripheral neuropathy in rats. Turk J Med Sci. 2021 Jun 13. doi: 10.3906/sag-2101-224. Epub ahead of print. PMID: 34118805. 2. Sultan M, Alghetaa H, Mohammed A, Abdulla OA, Wisniewski PJ, Singh N, Nagarkatti P, Nagarkatti M. The Endocannabinoid Anandamide Attenuates Acute Respiratory Distress Syndrome by Downregulating miRNA that Target Inflammatory Pathways. Front Pharmacol. 2021 Apr 27;12:644281. doi: 10.3389/fphar.2021.644281. PMID: 33995054; PMCID: PMC8113864.
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Front Mol Neurosci. 2025 Mar 12;18:1534324. doi: 10.3389/fnmol.2025.1534324. PMID: 40144805; PMCID: PMC11937075. 5: Fan ZK, Chen YF, Han WW, Guo XF, Li D. Coffee peel polyphenols ameliorate nonalcoholic fatty liver disease by modulating cannabinoid receptor type-1-ceramide axis. Phytother Res. 2025 Mar 26. doi: 10.1002/ptr.8078. Epub ahead of print. PMID: 40135380. 6: Lim J, Quach C, Nguyen J, Rizk A, Getze S, Jung KM, Mahler SV, Piomelli D, Luderer U. Adolescent exposure to Δ9-tetrahydrocannabinol (THC) impairs testicular function in young adult male mice. Toxicol Sci. 2025 Mar 24:kfaf035. doi: 10.1093/toxsci/kfaf035. Epub ahead of print. PMID: 40127192. 7: Maccioni L, Dvorácskó S, Godlewski G, Cinar R, Iyer MR, Gao B, Kunos G. Gut cannabinoid receptor 1 regulates alcohol binge-induced intestinal permeability. eGastroenterology. 2025 Feb 12;3(1):e100173. doi: 10.1136/egastro-2024-100173. PMID: 40124989; PMCID: PMC11927431. 8: Alayoubi M, Rodrigues A, Wu C, Whitehouse E, Nguyen J, Cooper ZD, O'Neill PR, Cahill CM. Elucidating interplay between myrcene and cannabinoid receptor 1 receptors to produce antinociception in mouse models of neuropathic pain. Pain. 2025 Mar 18. doi: 10.1097/j.pain.0000000000003558. Epub ahead of print. PMID: 40096521. 9: Shreya S, Dagar N, Gaikwad AB. Unlocking the therapeutic potential of the NFAT pathway in kidney diseases. Naunyn Schmiedebergs Arch Pharmacol. 2025 Mar 15. doi: 10.1007/s00210-025-04033-x. Epub ahead of print. PMID: 40088333. 10: García-Hernández VM, Torres-Román AL, Ruiz-García E, Santamaría A, Manzo- Merino J, García-López A, Angélica-Lezama R, Matus-Santos JA, Prospéro-García O, Navarro-Ríos J, Ortega-Gómez A. Pro-Apoptotic Effects of Anandamide in Human Gastric Cancer Cells Are Mediated by AKT and ERK Signaling Pathways. Int J Mol Sci. 2025 Feb 26;26(5):2033. doi: 10.3390/ijms26052033. PMID: 40076652; PMCID: PMC11900069. 11: Ehrlich B, Patel M, Zheng X, Glass M. Canonical Cannabinoid Receptors. Curr Top Behav Neurosci. 2025 Mar 7. doi: 10.1007/7854_2024_556. Epub ahead of print. PMID: 40050540. 12: Chen C, Wang W, Poklis JL, Li PL, Lichtman AH, Gewirtz DA, Li N. Mitigation of cisplatin-induced acute kidney injury through oral administration of fatty acid amide hydrolase inhibitor PF-04457845. J Pharmacol Exp Ther. 2025 Feb;392(2):100032. doi: 10.1124/jpet.124.002282. Epub 2024 Nov 22. PMID: 40023608. 13: Chua A, McMichael MA, Jukier T, Arnold RD, Hung WE, Harris S, Zhang C, Bustamante HA. Premedication and general anesthetic agents decrease plasma concentration of the endocannabinoid anandamide in dogs. Am J Vet Res. 2025 Feb 27:1-7. doi: 10.2460/ajvr.24.11.0366. Epub ahead of print. PMID: 40014917. 14: Pérez-Machín R, Vega-Morales T, Elvira-Aranda C, Lledó-Rico L, Gomis-Gomis MJ, López-Ríos L. 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Gut microbiota interacting with vitamin D but not anandamide might contribute to the pathogenesis of preeclampsia: a preliminary study. Front Cell Infect Microbiol. 2025 Feb 5;14:1469054. doi: 10.3389/fcimb.2024.1469054. PMID: 39973918; PMCID: PMC11835824. 20: Aloisio Caruso E, De Nunzio V, Tutino V, Notarnicola M. The Endocannabinoid System: Implications in Gastrointestinal Physiology and Pathology. Int J Mol Sci. 2025 Feb 3;26(3):1306. doi: 10.3390/ijms26031306. PMID: 39941074; PMCID: PMC11818434.