| Identification | Back Directory | [Name]
ARACHIDONOYL SERINOL | [CAS]
183718-70-9 | [Synonyms]
ARACHIDONOYL SERINOL
N-[(2-HYDROXY-1-HYDROXYMETHYL)ETHYL]-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide
5,8,11,14-Eicosatetraenamide, N-[2-hydroxy-1-(hydroxymethyl)ethyl]-, (5Z,8Z,11Z,14Z)- | [Molecular Formula]
C23H39NO3 | [MDL Number]
MFCD05863967 | [MOL File]
183718-70-9.mol | [Molecular Weight]
377.56 |
| Chemical Properties | Back Directory | [Boiling point ]
569.9±50.0 °C(Predicted) | [density ]
0.983±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide | [form ]
solution in ethanol. | [pka]
13.97±0.10(Predicted) | [color ]
Off-white to light yellow |
| Hazard Information | Back Directory | [Definition]
ChEBI: N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(1,3-dihydroxy-propyl-2-amine) is a fatty amide. | [Biological Activity]
arachidonoyl serinol is an amide bond-containing analogue of 2-arachidonoylglycerol, exhibited only weak cb1 receptor agonistic activity. 2-arachidonoyl glycerol (2-ag), a product of increased inositol phospholipid metabolism, is the natural endocannabinoid ligand for the cb1 receptor [1][2][3].cannabinoid receptor (cb1) was first identified in rat brain in 1988. n-arachidonoylethanolamine (anandamide) binds to the cannabinoid receptor and exhibits various cannabimimetic activities. anandamide inhibits calcium currents in n18 neuroblastoma cells, inhibits forskolin-stimulated adenylase cyclase activity, electrically evokes twitch response of the mouse vas deferens, and causes analgesia, hypothermia, hypoactivity, and catalepsy [3]. anandamide acts as a weak agonist and 2-arachidonoylglycerol may be an endogenous cannabinoid receptor agonist in nervous tissues [1].replacement of the sn-2 oxygen in the glycerol moiety of 2-ag with a nitrogen atom produces arachidonoyl serinol. in ng108-15 cells, arachidonoyl serinol induced a weak elevation of [ca2+]i [1][2]. | [storage]
Store at -20°C | [References]
[1]. sugiura t, kodaka t, kondo s, et al. 2-arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free ca2+ in neuroblastoma x glioma hybrid ng108-15 cells. biochem biophys res commun. 1996 dec 4;229(1):58-64.
[2]. sugiura t1, kodaka t, kondo s, et al. is the cannabinoid cb1 receptor a 2-arachidonoylglycerol receptor? structural requirements for triggering a ca2+ transient in ng108-15 cells. j biochem. 1997 oct;122(4):890-5.
[3]. khanolkar ad, abadji v, lin s, et al. head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. j med chem. 1996 oct 25;39(22):4515-9. |
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