AM-404
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MedKoo CAT#: 563426

CAS#: 183718-77-6

Description: AM-404 is a selective inhibitor of the carrier-mediated transport of anandamide without affecting anandamide hydrolysis.


Chemical Structure

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AM-404
CAS# 183718-77-6

Theoretical Analysis

MedKoo Cat#: 563426
Name: AM-404
CAS#: 183718-77-6
Chemical Formula: C26H37NO2
Exact Mass: 395.2824
Molecular Weight: 395.58
Elemental Analysis: C, 78.94; H, 9.43; N, 3.54; O, 8.09

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: AM-404; AM 404; AM404;

IUPAC/Chemical Name: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

InChi Key: IJBZOOZRAXHERC-DOFZRALJSA-N

InChi Code: InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-

SMILES Code: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NC1=CC=C(O)C=C1)=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: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 395.58 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

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1: Gerits E, Spincemaille P, De Cremer K, De Brucker K, Beullens S, Thevissen K, Cammue BPA, Vandamme K, Fauvart M, Verstraeten N, Michiels J. Repurposing AM404 for the treatment of oral infections by Porphyromonas gingivalis. Clin Exp Dent Res. 2017 Apr 7;3(2):69-76. doi: 10.1002/cre2.65. eCollection 2017 Apr. PubMed PMID: 29744181; PubMed Central PMCID: PMC5719815.

2: Tóth VE, Fehér Á, Németh J, Gyertyán I, Zádori ZS, Gyires K. Modulation of central endocannabinoid system results in gastric mucosal protection in the rat. Brain Res Bull. 2018 May;139:224-234. doi: 10.1016/j.brainresbull.2018.02.012. Epub 2018 Feb 10. PubMed PMID: 29438780.

3: Stueber T, Meyer S, Jangra A, Hage A, Eberhardt M, Leffler A. Activation of the capsaicin-receptor TRPV1 by the acetaminophen metabolite N-arachidonoylaminophenol results in cytotoxicity. Life Sci. 2018 Feb 1;194:67-74. doi: 10.1016/j.lfs.2017.12.024. Epub 2017 Dec 19. PubMed PMID: 29273526.

4: Klinger-Gratz PP, Ralvenius WT, Neumann E, Kato A, Nyilas R, Lele Z, Katona I, Zeilhofer HU. Acetaminophen Relieves Inflammatory Pain through CB(1) Cannabinoid Receptors in the Rostral Ventromedial Medulla. J Neurosci. 2018 Jan 10;38(2):322-334. doi: 10.1523/JNEUROSCI.1945-17.2017. Epub 2017 Nov 22. PubMed PMID: 29167401.

5: Hillard CJ, Huang H, Vogt CD, Rodrigues BE, Neumann TS, Sem DS, Schroeder F, Cunningham CW. Endocannabinoid Transport Proteins: Discovery of Tools to Study Sterol Carrier Protein-2. Methods Enzymol. 2017;593:99-121. doi: 10.1016/bs.mie.2017.06.017. Epub 2017 Jul 17. PubMed PMID: 28750817.

6: Iring A, Hricisák L, Benyó Z. CB1 receptor-mediated respiratory depression by endocannabinoids. Respir Physiol Neurobiol. 2017 Jun;240:48-52. doi: 10.1016/j.resp.2017.02.011. Epub 2017 Feb 22. PubMed PMID: 28254562.

7: Micale V, Stepan J, Jurik A, Pamplona FA, Marsch R, Drago F, Eder M, Wotjak CT. Extinction of avoidance behavior by safety learning depends on endocannabinoid signaling in the hippocampus. J Psychiatr Res. 2017 Jul;90:46-59. doi: 10.1016/j.jpsychires.2017.02.002. Epub 2017 Feb 3. PubMed PMID: 28222356.

8: Trader DJ, Simanski S, Dickson P, Kodadek T. Establishment of a suite of assays that support the discovery of proteasome stimulators. Biochim Biophys Acta. 2017 Apr;1861(4):892-899. doi: 10.1016/j.bbagen.2017.01.003. Epub 2017 Jan 5. PubMed PMID: 28065760; PubMed Central PMCID: PMC5366797.

9: van Cleef KW, Overheul GJ, Thomassen MC, Marjakangas JM, van Rij RP. Escape Mutations in NS4B Render Dengue Virus Insensitive to the Antiviral Activity of the Paracetamol Metabolite AM404. Antimicrob Agents Chemother. 2016 Mar 25;60(4):2554-7. doi: 10.1128/AAC.02462-15. Print 2016 Apr. PubMed PMID: 26856827; PubMed Central PMCID: PMC4808173.

10: Schindler CW, Scherma M, Redhi GH, Vadivel SK, Makriyannis A, Goldberg SR, Justinova Z. Self-administration of the anandamide transport inhibitor AM404 by squirrel monkeys. Psychopharmacology (Berl). 2016 May;233(10):1867-77. doi: 10.1007/s00213-016-4211-3. Epub 2016 Jan 23. PubMed PMID: 26803499; PubMed Central PMCID: PMC4846479.

11: Shimizu T, Tanaka K, Shimizu S, Higashi Y, Yawata T, Nakamura K, Taniuchi K, Ueba T, Yuri K, Saito M. Possible inhibitory role of endogenous 2-arachidonoylglycerol as an endocannabinoid in (±)-epibatidine-induced activation of central adrenomedullary outflow in the rat. Neuropharmacology. 2015 Aug;95:278-89. doi: 10.1016/j.neuropharm.2015.03.034. Epub 2015 Apr 14. PubMed PMID: 25882827.

12: Llorente-Berzal A, Terzian AL, di Marzo V, Micale V, Viveros MP, Wotjak CT. 2-AG promotes the expression of conditioned fear via cannabinoid receptor type 1 on GABAergic neurons. Psychopharmacology (Berl). 2015 Aug;232(15):2811-25. doi: 10.1007/s00213-015-3917-y. Epub 2015 Mar 28. PubMed PMID: 25814137.

13: Shubina L, Aliev R, Kitchigina V. Attenuation of kainic acid-induced status epilepticus by inhibition of endocannabinoid transport and degradation in guinea pigs. Epilepsy Res. 2015 Mar;111:33-44. doi: 10.1016/j.eplepsyres.2015.01.003. Epub 2015 Jan 23. PubMed PMID: 25769371.

14: Lisboa SF, Borges AA, Nejo P, Fassini A, Guimarães FS, Resstel LB. Cannabinoid CB1 receptors in the dorsal hippocampus and prelimbic medial prefrontal cortex modulate anxiety-like behavior in rats: additional evidence. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Jun 3;59:76-83. doi: 10.1016/j.pnpbp.2015.01.005. Epub 2015 Jan 14. PubMed PMID: 25595265.

15: Caballero FJ, Soler-Torronteras R, Lara-Chica M, García V, Fiebich BL, Muñoz E, Calzado MA. AM404 inhibits NFAT and NF-κB signaling pathways and impairs migration and invasiveness of neuroblastoma cells. Eur J Pharmacol. 2015 Jan 5;746:221-32. doi: 10.1016/j.ejphar.2014.11.023. Epub 2014 Nov 25. PubMed PMID: 25460026.

16: Manna SS, Umathe SN. Paracetamol potentiates the antidepressant-like and anticompulsive-like effects of fluoxetine. Behav Pharmacol. 2015 Apr;26(3):268-81. doi: 10.1097/FBP.0000000000000104. PubMed PMID: 25340977.

17: Peng LM, Chen XP, Shi RZ, Chen L, Li YJ, Yang TL. Involvement of anandamide transporter in calcitonin gene-related peptide expression stimulated by nitroglycerin and influence of ALDH2 Glu504Lys polymorphism. J Cardiovasc Pharmacol. 2014 Nov;64(5):460-4. doi: 10.1097/FJC.0000000000000138. PubMed PMID: 25098345.

18: Tosun NC, Gunduz O, Ulugol A. Attenuation of serotonin-induced itch responses by inhibition of endocannabinoid degradative enzymes, fatty acid amide hydrolase and monoacylglycerol lipase. J Neural Transm (Vienna). 2015 Mar;122(3):363-7. doi: 10.1007/s00702-014-1251-x. Epub 2014 Jun 11. PubMed PMID: 24915981.

19: Almeida V, Peres FF, Levin R, Suiama MA, Calzavara MB, Zuardi AW, Hallak JE, Crippa JA, Abílio VC. Effects of cannabinoid and vanilloid drugs on positive and negative-like symptoms on an animal model of schizophrenia: the SHR strain. Schizophr Res. 2014 Mar;153(1-3):150-9. doi: 10.1016/j.schres.2014.01.039. Epub 2014 Feb 18. PubMed PMID: 24556469.

20: Liedhegner ES, Vogt CD, Sem DS, Cunningham CW, Hillard CJ. Sterol carrier protein-2: binding protein for endocannabinoids. Mol Neurobiol. 2014 Aug;50(1):149-58. doi: 10.1007/s12035-014-8651-7. Epub 2014 Feb 9. PubMed PMID: 24510313; PubMed Central PMCID: PMC4450258.