MAFP (CAS 188404-10-6)

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Alternate Names: Methyl Arachidonyl Fluorophosphonate; Methylphosphonofluoridic acid 5,8,11,14-eicosatetraenyl ester

Application: MAFP is a potent, irreversible inhibitor of fatty acid amide hydrolase

CAS Number: 188404-10-6

Molecular Weight: 370.49

Molecular Formula: C₂₁H₃₆FO₂P

Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

* Refer to Certificate of Analysis for lot specific data (including water content).

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MAFP (methyl-arachidonoyl-fluoro-phosphonate) is an irreversible inhibitor of cPLA₂. Research has shown that this compound is also one of the most potent of the FAAH (anandamide amidohydrolase; Fatty acid amide hydrolase) inhibitors. Further studies suggest that MAFP completely blocks FAAH enzyme activity, the enzyme responsible for hydrolysis of endogenous cannabinoid ligand anandamide. Mechanistic studies suggest that this reagent specifically targets and phosphorylates arachidonyl binding sites. MAFP is an inhibitor of AChE. MAFP is an inhibitor of CB1. MAFP is an inhibitor of group VI iPLA2.

References

1. De Petrocellis, L., et al. 1997. Biochem. Biophys. Res. Commun. 231: 82-88. PMID: 9070224
2. Deutsch, D.G., et al. 1997. Biochem. Pharmacol. 53: 255-260. PMID: 9065728
3. Martin, B.R., et al. 2000. J. Pharmacol. Exp. Ther. 294: 1209-1218. PMID: 10945879

Appearance :

Oil

Physical State :

Liquid

Solubility :

Soluble in methyl acetate, 100% ethanol (50 mg/ml), DMSO (50 mg/ml), DMF (~3 mg/ml), and 1:1 solution of ethanol: PES(pH7.2) (~0.5 mg/ml).

Storage :

Store at -20° C

Melting Point :

84.80° C (Predicted)

Boiling Point :

~455.29° C at 760 mmHg (Predicted)

Density :

~1.0 g/mL (Predicted)

Refractive Index :

n²⁰_D 1.47 (Predicted)

IC50 :

fatty acid amide hydrolase: IC₅₀ = 2.5 nM; CB1 receptor: IC₅₀ = 20 nM; Ca2+-independent iPLA2: IC₅₀ = 0.5 µM; A23187-induced arachidonic acid release from human platelets: IC₅₀ = 0.6 µM; cPLA2: IC₅₀ = 5 µM

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

PubChem CID :

10429254

MDL Number :

MFCD03095722

EC Number :

201-185-2

SMILES :

CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCCP(=O)(OC)F

Download SDS (MSDS)

Certificate of Analysis

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MAFP (CAS 188404-10-6) Product Citations

See how others have used MAFP (CAS 188404-10-6). Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 23451150 2013. PLoS ONE. 8: e57081.

PMID: # 23774297 2013. Biochimie. 95: 1677-88.

PMID: # 22767227 Cai, Q. et al. 2012. FASEB J. 26: 3306-20.

PMID: # 28455813 In Vitro Cell Dev Biol Anim. 421-429.

Citations 1 to 4 of 4 total

Rated 5 out of 5 by MS from Martin et al Martin et al. (PubMed ID 10945879) showed MAFP s ability to manipulate endogenous cannabinoid systems by inhibiting fatty acid amidohydrolase activity (FAAH). -SCBT Publication Review

Date published: 2015-05-15

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