Description
Synaptamide (162758-94-3) is an anandamide-like lipid mediator produced from DHA in the brain. Stimulates neurite growth, synaptogenesis and glutamatergic synaptic activity in developing hippocampal neurons at 10-100 nM.1Potently induces neuronal differentiation of neural stem cells.2Promotes growth of cortical axons via modulation of hedgehog signaling.3Binds to and activates orphan receptor GPR110, stimulating cAMP production at low nM concentrations.4Reduces LPS-induced TNFα production in cultured microglia cells and ameliorates LPS-induced neuroinflammation in a mouse model.5
Uses
Synaptamide is an endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function. It has potent synaptogenic activity and structural similarity to anandamide. Synaptamide is subjected to hydrolysis by fatty acid amide hydrolase, and can be oxygenated to bioactive metabolites.
Definition
ChEBI: N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine is an N-acylethanolamine 22:6 that is the ethanolamide of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid. It is an endocannabinoid and a N-acylethanolamine 22:6. It is functionally related to an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.
in vivo
Synaptamide (10 mg/kg; subcutaneously; daily for 7 days) promotes cognitive recovery in rats subjected to mild traumatic brain injury (mTBI)[1].
Synaptamide (2-10 mg/kg; adult male C57BL/6J mice) reduced the levels of nociceptive and inflammatory pain-related behaviour over 60 min in the intraplantar formaldehyde assay via both intraperitoneal and local intraplantar administration[2].
| Animal Model: | Male Wistar rats;260±20 g, age 3 months; mTBI model)[1] |
| Dosage: | 10 mg/kg |
| Administration: | Subcutaneously; daily for 7 days |
| Result: | Reversed the mTBI-induced cognitive deficits.
|
IC 50
CB1: 633 nM (Ki); CB2: 3843 nM (Ki)
References
[1] HEE-YONG KIM Arthur A S. Synaptamide, endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function[J]. Prostaglandins, leukotrienes, and essential fatty acids, 2013, 88 1: Pages 121-125. DOI:
10.1016/j.plefa.2012.08.002[2] MOHAMMAD A. RASHID. N-docosahexaenoylethanolamine is a potent neurogenic factor for neural stem cell differentiation[J]. Journal of Neurochemistry, 2013, 125 6: 869-884. DOI:
10.1111/jnc.12255[3] G. KHAREBAVA. N-docosahexaenoylethanolamine regulates Hedgehog signaling and promotes growth of cortical axons[J]. Biology Open, 2015, 4 1: 1660-1670. DOI:
10.1242/bio.013425[4] JI-WON LEE. Orphan GPR110 (ADGRF1) targeted by N-docosahexaenoylethanolamine in development of neurons and cognitive function[J]. Nature Communications, 2016, 7 1. DOI:
10.1038/ncomms13123[5] TAEYEOP PARK. N-Docosahexaenoylethanolamine ameliorates LPS-induced neuroinflammation via cAMP/PKA-dependent signaling[J]. Journal of Neuroinflammation, 2016, 13 1. DOI:
10.1186/s12974-016-0751-z
