Anandamide
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MedKoo CAT#: 525001

CAS#: 94421-68-8

Description: 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

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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: 361.526
Elemental Analysis: C, 73.09; H, 9.76; N, 3.87; O, 13.28

Price and Availability

Size Price Availability Quantity
5.0mg USD 170.0 2 Weeks
10.0mg USD 290.0 2 Weeks
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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: Solid powder

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

Product Data:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol:PBS (1:2) 8.5 23.51

Preparing Stock Solutions

The following data is based on the product molecular weight 361.526 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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1: Cui HJ, Liu S, Yang R, Fu GH, Lu Y. N-stearoyltyrosine protects primary cortical neurons against oxygen-glucose deprivation-induced apoptosis through inhibiting anandamide inactivation system. Neurosci Res. 2017 May 9. pii: S0168-0102(17)30012-3. doi: 10.1016/j.neures.2017.04.019. [Epub ahead of print] PubMed PMID: 28499834.

2: King-Himmelreich TS, Möser CV, Wolters MC, Schmetzer J, Schreiber Y, Ferreirós N, Russe OQ, Geisslinger G, Niederberger E. AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids. Neuropharmacology. 2017 May 4. pii: S0028-3908(17)30198-3. doi: 10.1016/j.neuropharm.2017.05.002. [Epub ahead of print] PubMed PMID: 28479394.

3: Pirone A, Lenzi C, Briganti A, Abbate F, Levanti M, Abramo F, Miragliotta V. Spatial distribution of cannabinoid receptor 1 and fatty acid amide hydrolase in the cat ovary and oviduct. Acta Histochem. 2017 May;119(4):417-422. doi: 10.1016/j.acthis.2017.04.007. Epub 2017 May 4. PubMed PMID: 28478955.

4: Nerandzic V, Mrozkova P, Adamek P, Spicarova D, Nagy I, Palecek J. Peripheral inflammation alters N-arachidonoylphosphatidylethanolamine (20:4-NAPE) induced modulation of nociceptive spinal cord synaptic transmission. Br J Pharmacol. 2017 May 5. doi: 10.1111/bph.13849. [Epub ahead of print] PubMed PMID: 28476070.

5: Kimberly WT, O'Sullivan JF, Nath AK, Keyes M, Shi X, Larson MG, Yang Q, Long MT, Vasan R, Peterson RT, Wang TJ, Corey KE, Gerszten RE. Metabolite profiling identifies anandamide as a biomarker of nonalcoholic steatohepatitis. JCI Insight. 2017 May 4;2(9). pii: 92989. doi: 10.1172/jci.insight.92989. [Epub ahead of print] PubMed PMID: 28469090; PubMed Central PMCID: PMC5414569.

6: Almeida-Santos AF, Moreira FA, Guimaraes FS, Aguiar DC. 2-Arachidonoylglycerol endocannabinoid signaling coupled to metabotropic glutamate receptor type-5 modulates anxiety-like behavior in the rat ventromedial prefrontal cortex. J Psychopharmacol. 2017 Apr 1:269881117704986. doi: 10.1177/0269881117704986. [Epub ahead of print] PubMed PMID: 28440729.

7: Acharya N, Penukonda S, Shcheglova T, Hagymasi AT, Basu S, Srivastava PK. Endocannabinoid system acts as a regulator of immune homeostasis in the gut. Proc Natl Acad Sci U S A. 2017 May 9;114(19):5005-5010. doi: 10.1073/pnas.1612177114. Epub 2017 Apr 24. PubMed PMID: 28439004.

8: Bedse G, Hartley ND, Neale E, Gaulden AD, Patrick TA, Kingsley PJ, Uddin MJ, Plath N, Marnett LJ, Patel S. Functional Redundancy Between Canonical Endocannabinoid Signaling Systems in the Modulation of Anxiety. Biol Psychiatry. 2017 Mar 15. pii: S0006-3223(17)31357-4. doi: 10.1016/j.biopsych.2017.03.002. [Epub ahead of print] PubMed PMID: 28438413.

9: Karwad MA, Couch DG, Theophilidou E, Sarmad S, Barrett DA, Larvin M, Wright KL, Lund JN, O'Sullivan SE. The role of CB(1) in intestinal permeability and inflammation. FASEB J. 2017 Apr 12. pii: fj.201601346R. doi: 10.1096/fj.201601346R. [Epub ahead of print] PubMed PMID: 28404744.

10: Soni N, Prabhala BK, Mehta V, Mirza O, Kohlmeier KA. Anandamide and 2-AG Are Endogenously Present within the Laterodorsal Tegmental Nucleus: Functional Implications for a role of eCBs in arousal. Brain Res. 2017 Apr 9. pii: S0006-8993(17)30157-9. doi: 10.1016/j.brainres.2017.04.003. [Epub ahead of print] PubMed PMID: 28404451.

11: Di Scala C, Mazzarino M, Yahi N, Varini K, Garmy N, Fantini J, Chahinian H. Ceramide binding to anandamide increases its half-life and potentiates its cytotoxicity in human neuroblastoma cells. Chem Phys Lipids. 2017 Apr 4;205:11-17. doi: 10.1016/j.chemphyslip.2017.04.001. [Epub ahead of print] PubMed PMID: 28389107.

12: Chaikin P. The Bial 10-2474 Phase 1 Study-A Drug Development Perspective and Recommendations for Future First-in-Human Trials. J Clin Pharmacol. 2017 Apr 7. doi: 10.1002/jcph.889. [Epub ahead of print] Review. PubMed PMID: 28387940.

13: Munawar N, Oriowo MA, Masocha W. Antihyperalgesic Activities of Endocannabinoids in a Mouse Model of Antiretroviral-Induced Neuropathic Pain. Front Pharmacol. 2017 Mar 20;8:136. doi: 10.3389/fphar.2017.00136. eCollection 2017. PubMed PMID: 28373843; PubMed Central PMCID: PMC5357623.

14: Karpińska O, Baranowska-Kuczko M, Kloza M, Ambrożewicz E, Kozłowski T, Kasacka I, Malinowska B, Kozłowska H. Activation of CB(1) receptors by 2-arachidonoylglycerol attenuates vasoconstriction induced by U46619 and angiotensin II in human and rat pulmonary arteries. Am J Physiol Regul Integr Comp Physiol. 2017 Mar 29:ajpregu.00324.2016. doi: 10.1152/ajpregu.00324.2016. [Epub ahead of print] PubMed PMID: 28356298.

15: Ramírez-López MT, Vázquez M, Lomazzo E, Hofmann C, Blanco RN, Alén F, Antón M, Decara J, Arco R, Orio L, Suárez J, Lutz B, Gómez de Heras R, Bindila L, Rodríguez de Fonseca F. A moderate diet restriction during pregnancy alters the levels of endocannabinoids and endocannabinoid-related lipids in the hypothalamus, hippocampus and olfactory bulb of rat offspring in a sex-specific manner. PLoS One. 2017 Mar 27;12(3):e0174307. doi: 10.1371/journal.pone.0174307. eCollection 2017. PubMed PMID: 28346523; PubMed Central PMCID: PMC5367805.

16: Mela V, Piscitelli F, Berzal AL, Chowen J, Silvestri C, Viveros MP, Di Marzo V. Sex-dependent effects of neonatal maternal deprivation on endocannabinoid levels in the adipose tissue: influence of diet. J Physiol Biochem. 2017 Mar 23. doi: 10.1007/s13105-017-0558-0. [Epub ahead of print] PubMed PMID: 28337718.

17: Marchioni C, de Souza ID, Grecco CF, Crippa JA, Tumas V, Queiroz MEC. A column switching ultrahigh-performance liquid chromatography-tandem mass spectrometry method to determine anandamide and 2-arachidonoylglycerol in plasma samples. Anal Bioanal Chem. 2017 May;409(14):3587-3596. doi: 10.1007/s00216-017-0300-3. Epub 2017 Mar 23. PubMed PMID: 28337517.

18: Maglio LE, Noriega-Prieto JA, Maraver MJ, Fernández de Sevilla D. Endocannabinoid-Dependent Long-Term Potentiation of Synaptic Transmission at Rat Barrel Cortex. Cereb Cortex. 2017 Mar 1:1-14. doi: 10.1093/cercor/bhx053. [Epub ahead of print] PubMed PMID: 28334325.

19: Bondarenko AI, Panasiuk O, Okhai I, Montecucco F, Brandt KJ, Mach F. Direct activation of Ca(2+) and voltage-gated potassium channels of large conductance by anandamide in endothelial cells does not support the presence of endothelial atypical cannabinoid receptor. Eur J Pharmacol. 2017 Jun 15;805:14-24. doi: 10.1016/j.ejphar.2017.03.038. Epub 2017 Mar 19. PubMed PMID: 28327344.

20: Peng X, Studholme K, Kanjiya MP, Luk J, Bogdan D, Elmes MW, Carbonetti G, Tong S, Gary Teng YH, Rizzo RC, Li H, Deutsch DG, Ojima I, Rebecchi MJ, Puopolo M, Kaczocha M. Fatty-acid-binding protein inhibition produces analgesic effects through peripheral and central mechanisms. Mol Pain. 2017 Jan;13:1744806917697007. doi: 10.1177/1744806917697007. PubMed PMID: 28326944; PubMed Central PMCID: PMC5407663.