Arachidonoyl serotonin
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Hodoodo CAT#: H561063

CAS#: 187947-37-1

Description: AA-5HT, also known as Arachidonoyl serotonin or N-arachidonoyl-serotonin, is an inhibitor of fatty acid amide hydrolase (FAAH). It has analgesic properties and acts as an antagonist of the TRPV1 receptor. It was shown to be present in the ileum and jejunum of the gastrointestinal tract and modulate glucagon-like peptide-1 (GLP-1) secretion.

Chemical Structure

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Arachidonoyl serotonin
CAS# 187947-37-1
Instruction

Theoretical Analysis

Hodoodo Cat#: H561063
Name: Arachidonoyl serotonin
CAS#: 187947-37-1
Chemical Formula: C30H42N2O2
Exact Mass: 462.32
Molecular Weight: 462.678
Elemental Analysis: C, 77.88; H, 9.15; N, 6.05; O, 6.92

Price and Availability

Size Price Availability Quantity
10mg USD 155 2 Weeks
20mg USD 265 2 Weeks
50mg USD 550 2 Weeks
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Synonym: AA-5HT; AA5HT; AA 5HT; N-arachidonoyl-serotonin; Arachidonoyl serotonin

IUPAC/Chemical Name: (5Z,8Z,11Z,14Z)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)icosa-5,8,11,14-tetraenamide

InChi Key: QJDNHGXNNRLIGA-DOFZRALJSA-N

InChi Code: InChI=1S/C30H42N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(34)31-23-22-26-25-32-29-21-20-27(33)24-28(26)29/h6-7,9-10,12-13,15-16,20-21,24-25,32-33H,2-5,8,11,14,17-19,22-23H2,1H3,(H,31,34)/b7-6-,10-9-,13-12-,16-15-

SMILES Code: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCC1=CNC2=C1C=C(O)C=C2)=O

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 462.68 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:
In vitro protocol:
In vivo protocol:

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1: Arnold WR, Carnevale LN, Xie Z, Baylon JL, Tajkhorshid E, Hu H, Das A. Anti- inflammatory dopamine- and serotonin-based endocannabinoid epoxides reciprocally regulate cannabinoid receptors and the TRPV1 channel. Nat Commun. 2021 Feb 10;12(1):926. doi: 10.1038/s41467-021-20946-6. PMID: 33568652; PMCID: PMC7876028.


2: Freels TG, Lester DB, Cook MN. Arachidonoyl serotonin (AA-5-HT) modulates general fear-like behavior and inhibits mesolimbic dopamine release. Behav Brain Res. 2019 Apr 19;362:140-151. doi: 10.1016/j.bbr.2019.01.010. Epub 2019 Jan 11. PMID: 30639609.


3: Gobira PH, Lima IV, Batista LA, de Oliveira AC, Resstel LB, Wotjak CT, Aguiar DC, Moreira FA. N-arachidonoyl-serotonin, a dual FAAH and TRPV1 blocker, inhibits the retrieval of contextual fear memory: Role of the cannabinoid CB1 receptor in the dorsal hippocampus. J Psychopharmacol. 2017 Jun;31(6):750-756. doi: 10.1177/0269881117691567. Epub 2017 Feb 21. PMID: 28583049.


4: John CS, Currie PJ. N-arachidonoyl-serotonin in the basolateral amygdala increases anxiolytic behavior in the elevated plus maze. Behav Brain Res. 2012 Aug 1;233(2):382-8. doi: 10.1016/j.bbr.2012.05.025. Epub 2012 May 23. PMID: 22633963.


5: Jeon HL, Yoo JM, Lee BD, Lee SJ, Sohn EJ, Kim MR. Anti-Inflammatory and Antioxidant Actions of N-Arachidonoyl Serotonin in RAW264.7 Cells. Pharmacology. 2016;97(3-4):195-206. doi: 10.1159/000443739. Epub 2016 Feb 10. PMID: 26859139.


6: Murillo-Rodríguez E, Di Marzo V, Machado S, Rocha NB, Veras AB, Neto GAM, Budde H, Arias-Carrión O, Arankowsky-Sandoval G. Role of N-Arachidonoyl- Serotonin (AA-5-HT) in Sleep-Wake Cycle Architecture, Sleep Homeostasis, and Neurotransmitters Regulation. Front Mol Neurosci. 2017 May 30;10:152. doi: 10.3389/fnmol.2017.00152. PMID: 28611585; PMCID: PMC5447686.


7: Fowler CJ, Tiger G, López-Rodríguez ML, Viso A, Ortega-Gutiérrez S, Ramos JA. Inhibition of fatty acid amidohydrolase, the enzyme responsible for the metabolism of the endocannabinoid anandamide, by analogues of arachidonoyl- serotonin. J Enzyme Inhib Med Chem. 2003 Jun;18(3):225-31. doi: 10.1080/1475636031000080216. PMID: 14506913.


8: Vilela LR, Medeiros DC, de Oliveira AC, Moraes MF, Moreira FA. Anticonvulsant effects of N-arachidonoyl-serotonin, a dual fatty acid amide hydrolase enzyme and transient receptor potential vanilloid type-1 (TRPV1) channel blocker, on experimental seizures: the roles of cannabinoid CB1 receptors and TRPV1 channels. Basic Clin Pharmacol Toxicol. 2014 Oct;115(4):330-4. doi: 10.1111/bcpt.12232. Epub 2014 Apr 15. PMID: 24674273.


9: Wang Y, Balvers MGJ, Hendriks HFJ, Wilpshaar T, van Heek T, Witkamp RF, Meijerink J. Docosahexaenoyl serotonin emerges as most potent inhibitor of IL-17 and CCL-20 released by blood mononuclear cells from a series of N-acyl serotonins identified in human intestinal tissue. Biochim Biophys Acta Mol Cell Biol Lipids. 2017 Sep;1862(9):823-831. doi: 10.1016/j.bbalip.2017.05.008. Epub 2017 May 16. PMID: 28526351.


10: Park HY, Ryu YK, Go J, Son E, Kim KS, Kim MR. Palmitoyl Serotonin Inhibits L-dopa-induced Abnormal Involuntary Movements in the Mouse Parkinson Model. Exp Neurobiol. 2016 Aug;25(4):174-84. doi: 10.5607/en.2016.25.4.174. Epub 2016 Aug 8. PMID: 27574484; PMCID: PMC4999423.


11: Gholami S, Bordbar AK, Akvan N. Spectroscopic and dynamic properties of arachidonoyl serotonin- β-lactoglobulin complex: A molecular modeling and chemometric study. J Photochem Photobiol B. 2016 Sep;162:519-528. doi: 10.1016/j.jphotobiol.2016.07.024. Epub 2016 Jul 21. PMID: 27472903.


12: Rose TM, Reilly CA, Deering-Rice CE, Brewster C, Brewster C. Inhibition of FAAH, TRPV1, and COX2 by NSAID-serotonin conjugates. Bioorg Med Chem Lett. 2014 Dec 15;24(24):5695-5698. doi: 10.1016/j.bmcl.2014.10.064. Epub 2014 Oct 28. PMID: 25467164; PMCID: PMC4258163.


13: Kaczyńska K, Szereda-Przestaszewska M. Nodose ganglia-modulatory effects on respiration. Physiol Res. 2013;62(3):227-35. doi: 10.33549/physiolres.932412. Epub 2013 Mar 14. PMID: 23489183.


14: Maione S, De Petrocellis L, de Novellis V, Moriello AS, Petrosino S, Palazzo E, Rossi FS, Woodward DF, Di Marzo V. Analgesic actions of N-arachidonoyl- serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors. Br J Pharmacol. 2007 Mar;150(6):766-81. doi: 10.1038/sj.bjp.0707145. Epub 2007 Feb 5. PMID: 17279090; PMCID: PMC2013858.


15: de Novellis V, Palazzo E, Rossi F, De Petrocellis L, Petrosino S, Guida F, Luongo L, Migliozzi A, Cristino L, Marabese I, Starowicz K, Di Marzo V, Maione S; Endocannabinoid Research Group. The analgesic effect of N-arachidonoyl- serotonin, a FAAH inhibitor and TRPV1 receptor antagonist, associated with changes in rostral ventromedial medulla and locus coeruleus cell activity in rats. Neuropharmacology. 2008 Dec;55(7):1105-13. doi: 10.1016/j.neuropharm.2008.06.023. Epub 2008 Jun 20. PMID: 18616956.


16: Costa B, Bettoni I, Petrosino S, Comelli F, Giagnoni G, Di Marzo V. The dual fatty acid amide hydrolase/TRPV1 blocker, N-arachidonoyl-serotonin, relieves carrageenan-induced inflammation and hyperalgesia in mice. Pharmacol Res. 2010 Jun;61(6):537-46. doi: 10.1016/j.phrs.2010.02.001. Epub 2010 Feb 6. PMID: 20138997.


17: Bashashati M, Fichna J, Piscitelli F, Capasso R, Izzo AA, Sibaev A, Timmermans JP, Cenac N, Vergnolle N, Di Marzo V, Storr M. Targeting fatty acid amide hydrolase and transient receptor potential vanilloid-1 simultaneously to modulate colonic motility and visceral sensation in the mouse: A pharmacological intervention with N-arachidonoyl-serotonin (AA-5-HT). Neurogastroenterol Motil. 2017 Dec;29(12). doi: 10.1111/nmo.13148. Epub 2017 Jul 11. PMID: 28695708.


18: Piscitelli F, Bradshaw HB. Endocannabinoid Analytical Methodologies: Techniques That Drive Discoveries That Drive Techniques. Adv Pharmacol. 2017;80:1-30. doi: 10.1016/bs.apha.2017.04.003. Epub 2017 Jul 3. PMID: 28826532.


19: Nguyen MD, Nguyen DH, Yoo JM, Myung PK, Kim MR, Sok DE. Effect of endocannabinoids on soybean lipoxygenase-1 activity. Bioorg Chem. 2013 Aug;49:24-32. doi: 10.1016/j.bioorg.2013.06.001. Epub 2013 Jun 13. PMID: 23856367.


20: Sakane F, Hoshino F, Murakami C. New Era of Diacylglycerol Kinase, Phosphatidic Acid and Phosphatidic Acid-Binding Protein. Int J Mol Sci. 2020 Sep 16;21(18):6794. doi: 10.3390/ijms21186794. PMID: 32947951; PMCID: PMC7555651.