| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| Other Sizes |
| Targets |
IC50: 13 nM (amidase)[1]
AM 374 targets fatty acid amide hydrolase (FAAH), the primary enzyme that hydrolyzes the endocannabinoid anandamide. By inhibiting FAAH, AM 374 prevents the breakdown of anandamide, leading to enhanced endocannabinoid signaling. The compound shows potent inhibition with an IC50 of 13 nM. |
|---|---|
| ln Vitro |
In N18TG2 cells, AM 374 (0–9 nM) inhibits the breakdown of anandamide [1].
In cell-free enzyme assays, AM 374 potently inhibits FAAH activity with an IC50 of 13 nM. The compound acts as a competitive inhibitor of the enzyme, blocking the hydrolysis of anandamide and other fatty acid amides. Its sulfonyl fluoride moiety forms a covalent bond with the active site serine residue of FAAH, resulting in irreversible inhibition. Cellular studies demonstrate that AM 374 potently inhibits endogenous amidase activity in hippocampal tissue, facilitating access of exogenous anandamide to cannabinoid receptors. The compound enhances the potency of exogenously added anandamide in hippocampal slice preparations, confirming its ability to inhibit FAAH in intact tissue. |
| ln Vivo |
AM 374 (20 μg; intraventricular injection, once) has no effect on FR5 lever pushing, however when given in conjunction with anandamide (ip), it decreases lever pressing[2].
In vivo, AM 374 potentiates the action of anandamide on hippocampal slices by inhibiting endogenous FAAH activity. The compound facilitates access of exogenous anandamide to cannabinoid receptors in hippocampal tissue. These effects are consistent with FAAH inhibition leading to elevated endocannabinoid levels. In vivo studies have demonstrated the compound's ability to modulate cannabinoid receptor-mediated signaling. |
| Enzyme Assay |
FAAH enzyme assays for AM 374 are performed using recombinant FAAH or tissue homogenates. The enzyme is incubated with a fluorogenic substrate (e.g., anandamide analog) and varying concentrations of AM 374. Hydrolysis product formation is measured fluorometrically or by radiometric detection. IC50 values are calculated from inhibition curves. The compound's irreversible inhibition mechanism is confirmed by pre-incubation studies.
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| Cell Assay |
Cellular FAAH activity assays are conducted using cultured cells or tissue slices expressing FAAH. Cells are treated with AM 374 at various concentrations, then a FAAH substrate is added. Product formation is measured by HPLC or mass spectrometry. The compound's ability to potentiate anandamide effects is assessed in hippocampal slice preparations by measuring cannabinoid receptor-mediated responses.
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| Animal Protocol |
Animal/Disease Models: Adult male SD (Sprague-Dawley) rats with lever press training[2]
Doses: 20 μg Route of Administration: Intraventricular (ICV) injection; 20 μg, once Experimental Results: Dramatically decreased lever pressing when combined treatment with anandamide. |
| ADME/Pharmacokinetics |
Pharmacokinetic properties of AM 374 have been partially characterized. As a sulfonyl fluoride compound, it is reactive and may have limited systemic bioavailability. The compound is typically used in ex vivo or in vitro preparations. Detailed PK parameters including half-life and tissue distribution require further investigation.
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| Toxicity/Toxicokinetics |
AM 374 is a reactive compound due to its sulfonyl fluoride moiety, which covalently modifies FAAH. Proper handling with appropriate safety precautions is required. Toxicity data are limited, but the compound is used in research settings at low concentrations. Its irreversible inhibition mechanism necessitates careful dose selection in experimental protocols.
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| References |
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| Additional Infomation |
Hexadecane-1-sulfonyl fluoride is an acyl fluoride. It is functionally related to hexadecane-1-sulfonic acid.
AM 374 is a research tool for studying the endocannabinoid system and FAAH function. It is one of the early FAAH inhibitors developed for investigating the role of anandamide in neurological processes. The compound has been used to study the potentiation of anandamide action in hippocampal slices. It is not approved for clinical use. |
| Molecular Formula |
C16H33FO2S
|
|---|---|
| Molecular Weight |
308.50
|
| Exact Mass |
308.219
|
| CAS # |
86855-26-7
|
| PubChem CID |
3572
|
| Appearance |
White to off-white solid powder
|
| Density |
0.966g/cm3
|
| Boiling Point |
388.3ºC at 760 mmHg
|
| Flash Point |
188.6ºC
|
| Index of Refraction |
1.445
|
| LogP |
6.847
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
15
|
| Heavy Atom Count |
20
|
| Complexity |
283
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCCCCCCCCCCS(=O)(=O)F
|
| 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
|
| Chemical Name |
hexadecane-1-sulfonyl fluoride
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (324.15 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.10 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (8.10 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.10 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2415 mL | 16.2075 mL | 32.4149 mL | |
| 5 mM | 0.6483 mL | 3.2415 mL | 6.4830 mL | |
| 10 mM | 0.3241 mL | 1.6207 mL | 3.2415 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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