Synaptamide

Names

[ Name ]:
Synaptamide

[Synonym ]:
4,7,10,13,16,19-Docosahexaenamide, N-(2-hydroxyethyl)-, (4Z,7Z,10Z,13Z,16Z,19Z)-
(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-Hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide,DEA,DHEA
(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-Hydroxyethyl)-4,7,10,13,16,19-docosahexaenamide
N-(2-hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide
Synaptamide

Biological Activity

[Description]:

Synaptamide is a potent mediator for neurogenic differentiation of NSCs acting through PKA/CREB activation.Target: in vitro: Synaptamide inhibits forskolin-mediated cAMP production (IC50 =6 μM) in CHO-HCR cells. Synaptamide decreases the viability of the LNCaP and PC3 prostate cancer cell lines (IC50=120-130 μM) grown in media containing 10% fetal bovine serum. [1] Synaptamide is an endogenous DHA metabolite with endocannabinoid-like structure, promotes neurite growth, synaptogenesis and synaptic function. Synaptamide potently induces neuronal differentiation of NSCs. Treatment of NSCs with Synaptamide at low nanomolar concentrations significantly increased the number of MAP2 and Tuj-1 positive neurons with concomitant induction of PKA/CREB phosphorylation. [2]

[Related Catalog]:

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA

Signaling Pathways >> Stem Cell/Wnt >> PKA

Research Areas >> Neurological Disease

[References]

[1]. Kim HY, et al. Synaptamide, endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function. Prostaglandins Leukot Essent Fatty Acids. 2013 Jan;88(1):121-5.

[2]. Rashid MA, et al. N-Docosahexaenoylethanolamine is a potent neurogenic factor for neural stem cell differentiation. J Neurochem. 2013 Jun;125(6):869-84.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
544.7±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₄H₃₇NO₂

[ Molecular Weight ]:
371.556

[ Flash Point ]:
283.3±30.1 °C

[ Exact Mass ]:
371.282440

[ PSA ]:
49.33000

[ LogP ]:
5.44

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.521

[ Storage condition ]:
-20°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport