| Identification | Back Directory | [Name]
HexadecanaMide, N-(phenylMethyl)- | [CAS]
74058-71-2 | [Synonyms]
Macamide 1
Macamide B
Macamide Impurity 4
N-benzylpalMitaMide
N-Benzylhexadecanamide
Hexadecanamide, N-benzyl-
Macamide B, Macamide Impurity 1
HexadecanaMide, N-(phenylMethyl)- | [Molecular Formula]
C23H39NO | [MDL Number]
MFCD00378779 | [MOL File]
74058-71-2.mol | [Molecular Weight]
345.56 |
| Chemical Properties | Back Directory | [Melting point ]
95-96℃ | [Boiling point ]
501.9±29.0 °C(Predicted) | [density ]
0.919±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
≤2mg/ml in organic solvent ethanol | [form ]
crystalline solid | [pka]
16.39±0.46(Predicted) |
| Hazard Information | Back Directory | [Uses]
N-Benzyl Hexadecanamide is a non-?polar, long-?chain fatty acid N-?benzylamide part of a group of macamides tested as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH)?. | [Definition]
ChEBI: N-benzylhexadecanamide is a macamide resulting from the formal condensation of the carboxy group of hexadecanoic acid with benzylamine. A moderate inhibitor of fatty acid amide hydrolase. It has a role as a neuroprotective agent, a plant metabolite and an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor. It is a secondary carboxamide and a macamide. It is functionally related to a hexadecanoic acid and a benzylamine. | [Biological Activity]
n-benzylpalmitamide is an inhibitor of fatty acid amide hydrolase (faah) [1].the fatty acid amide hydrolase (faah) is a mammalian integral membrane enzyme responsible for the hydrolysis of anandamide, an endocannabinoid. the faah is involved in degrading the fatty acid amide family of endogenous signaling lipids, including the endogenous cannabinoid anandamide and the sleep-inducing substance oleamide. faah belongs to is a member of amidase signature (as) family. the faah integrates into cell membranes and terminates fatty acid amide signaling in vivo [2]. genetic mutations in faah may constitute important risk factors for problem drug use and support a potential link between functional abnormalities in the endogenous cannabinoid system and drug abuse and dependence [3].n-benzylpalmitamide was a long-chain fatty acid amide isolated from the maca (l. meyenii) plant and was structurally related to cannabinoids. n-benzylpalmitamide was a moderate inhibitor of faah and inhibited 44% activity of faah at 500 μm [1]. | [References]
[1] wu h, kelley c j, pino-figueroa a, et al. macamides and their synthetic analogs: evaluation of in vitro faah inhibition[j]. bioorganic & medicinal chemistry, 2013, 21(17): 5188-5197.
[2] deutsch d g, ueda n, yamamoto s. the fatty acid amide hydrolase (faah)[j]. prostaglandins, leukotrienes and essential fatty acids (plefa), 2002, 66(2): 201-210.
[3] sipe j c, chiang k, gerber a l, et al. a missense mutation in human fatty acid amide hydrolase associated with problem drug use[j]. proceedings of the national academy of sciences, 2002, 99(12): 8394-8399. |
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