US EPA

7418430 

Journal Article 

Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition 

Wu, H; Kelley, CJ; Pino-Figueroa, A; Vu, HD; Maher, TJ; , 

2013 

Yes 

Bioorganic & Medicinal Chemistry
ISSN: 0968-0896
EISSN: 1464-3391 

PERGAMON-ELSEVIER SCIENCE LTD 

OXFORD 

21 

17 

5188-5197 

English 

23891163 

10.1016/j.bmc.2013.06.034 

WOS:000323294600035 

https://linkinghub.elsevier.com/retrieve/pii/S0968089613005658
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Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50=10-17μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50=0.153μM). 

Anandamide; Carbamate; FAAH 3-Methoxybenzylamine; Fatty acid amide; Lepidium meyenii; Maca; Macamide; OL-135; Oleamide; PF-750; Urea; 3 methoxybenzylamine; amide; anandamide; benzylamine; fatty acid amidase; fatty acid amidase inhibitor; linoleic acid; linolenic acid; macamide derivative; n (3 methoxybenzyl)octadeca 9,12 dienamide; n (3 methoxybenzyl)octadeca 9,12,15 trienamide; n (3 methoxybenzyl)oleamide; n (3 methoxybenzyl)palmitamide; n (3 methoxybenzyl)tetradecanamide; n (4 chlorobenzyl)palmitamide; n (4 fluorobenzyl)palmitamide; n benzyl 5 oxooctadeca 6,8 dienamide; n benzyllinoleamide; n benzyllinolenamide; n benzylnervonamide; n benzyloctadeca 9,12 dienamide; n benzyloctadeca 9,12,15 trienamide; n benzyloleamide; n benzylpalmitamide; n benzylstearamide; n benzyltetracos 15 enamide; n benzyltetradecanamide; oleamide; oleic acid; unclassified drug; unindexed drug; article; drug mechanism; drug potency; drug structure; drug synthesis; enzyme inhibition; IC 50; in vitro study; Lepidium meyenii; 3-Methoxybenzylamine; Anandamide; Carbamate; FAAH; Fatty acid amide; Lepidium meyenii; Maca; Macamide; OL-135; Oleamide; PF-750; Urea; Amides; Amidohydrolases; Enzyme Inhibitors; Humans; Hydrolysis; Lepidium; Protein Binding; Structure-Activity Relationship