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MedKoo Cat#: 574557 | Name: AM374
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Description:

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

AM374 is an inhibitor of fatty acid amide hydrolase (FAAH). M374 caused a prolonged elevation of anandamide levels in several brain regions, including the hippocampus, and resulted in rapid activation of the extracellular signal regulated-kinase/mitogen-activated protein kinase pathway that has been linked to survival. AM374 also preserved pre- and postsynaptic markers to levels comparable with those found in noninsulted animals, and the synaptic marker preservation strongly correlated with reduced seizure scores. With regard to behavioral deficits in the excitotoxic rats, AM374 produced nearly complete functional protection, significantly improving balance and coordination across different behavioral paradigms. These data indicate that AM374 crosses the blood-brain barrier, enhances endocannabinoid responses in key neuronal circuitries, and protects the brain against excitotoxic damage.

Chemical Structure

AM374
AM374
CAS#86855-26-7

Theoretical Analysis

MedKoo Cat#: 574557

Name: AM374

CAS#: 86855-26-7

Chemical Formula: C16H33FO2S

Exact Mass: 308.2185

Molecular Weight: 308.50

Elemental Analysis: C, 62.29; H, 10.78; F, 6.16; O, 10.37; S, 10.39

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
AM374, AM 374, AM-374; HDSF; Hexadecyl sulfonylfluoride
IUPAC/Chemical Name
Hexadecyl sulfonylfluoride
InChi Key
QIVFMUVBIHIZAM-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H33FO2S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(17,18)19/h2-16H2,1H3
SMILES Code
CCCCCCCCCCCCCCCCS(=O)(F)=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.50 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: Karanian DA, Karim SL, Wood JT, Williams JS, Lin S, Makriyannis A, Bahr BA. Endocannabinoid enhancement protects against kainic acid-induced seizures and associated brain damage. J Pharmacol Exp Ther. 2007 Sep;322(3):1059-66. doi: 10.1124/jpet.107.120147. Epub 2007 Jun 1. PMID: 17545313. 2: Karanian DA, Brown QB, Makriyannis A, Kosten TA, Bahr BA. Dual modulation of endocannabinoid transport and fatty acid amide hydrolase protects against excitotoxicity. J Neurosci. 2005 Aug 24;25(34):7813-20. doi: 10.1523/JNEUROSCI.2347-05.2005. PMID: 16120783; PMCID: PMC6725251. 3: Alapafuja SO, Nikas SP, Bharathan IT, Shukla VG, Nasr ML, Bowman AL, Zvonok N, Li J, Shi X, Engen JR, Makriyannis A. Sulfonyl fluoride inhibitors of fatty acid amide hydrolase. J Med Chem. 2012 Nov 26;55(22):10074-89. doi: 10.1021/jm301205j. Epub 2012 Nov 2. PMID: 23083016; PMCID: PMC3678964. 4: Arizzi MN, Cervone KM, Aberman JE, Betz A, Liu Q, Lin S, Makriyannis A, Salamone JD. Behavioral effects of inhibition of cannabinoid metabolism: The amidase inhibitor AM374 enhances the suppression of lever pressing produced by exogenously administered anandamide. Life Sci. 2004 Jan 9;74(8):1001-11. doi: 10.1016/j.lfs.2003.07.024. PMID: 14672756. 5: Deutsch DG, Lin S, Hill WA, Morse KL, Salehani D, Arreaza G, Omeir RL, Makriyannis A. Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor. Biochem Biophys Res Commun. 1997 Feb 3;231(1):217-21. doi: 10.1006/bbrc.1997.6072. PMID: 9070252. 6: Evagorou A, Anagnostopoulos D, Farmaki E, Siafaka-Kapadai A. Hydrolysis of 2-arachidonoylglycerol in Tetrahymena thermophila. Identification and partial characterization of a Monoacylglycerol Lipase-like enzyme. Eur J Protistol. 2010 Nov;46(4):289-97. doi: 10.1016/j.ejop.2010.06.001. PMID: 20889319. 7: Gkini E, Anagnostopoulos D, Mavri-Vavayianni M, Siafaka-Kapadai A. Metabolism of 2-acylglycerol in rabbit and human platelets. Involvement of monoacylglycerol lipase and fatty acid amide hydrolase. Platelets. 2009 Sep;20(6):376-85. doi: 10.1080/09537100903121813. PMID: 19811221. 8: Lastres-Becker I, de Miguel R, De Petrocellis L, Makriyannis A, Di Marzo V, Fernández-Ruiz J. Compounds acting at the endocannabinoid and/or endovanilloid systems reduce hyperkinesia in a rat model of Huntington's disease. J Neurochem. 2003 Mar;84(5):1097-109. doi: 10.1046/j.1471-4159.2003.01595.x. PMID: 12603833. 9: Rice AS. Cannabinoids and pain. Curr Opin Investig Drugs. 2001 Mar;2(3):399-414. PMID: 11575713. 10: Williams J, Wood J, Pandarinathan L, Karanian DA, Bahr BA, Vouros P, Makriyannis A. Quantitative method for the profiling of the endocannabinoid metabolome by LC-atmospheric pressure chemical ionization-MS. Anal Chem. 2007 Aug 1;79(15):5582-93. doi: 10.1021/ac0624086. Epub 2007 Jun 29. PMID: 17600384. 11: Gifford AN, Bruneus M, Lin S, Goutopoulos A, Makriyannis A, Volkow ND, Gatley SJ. Potentiation of the action of anandamide on hippocampal slices by the fatty acid amide hydrolase inhibitor, palmitylsulphonyl fluoride (AM 374). Eur J Pharmacol. 1999 Oct 21;383(1):9-14. doi: 10.1016/s0014-2999(99)00609-3. PMID: 10556675.