| Identification | Back Directory | [Name]
Dehydroepiandrosteron(DHEA) | [CAS]
162758-94-3 | [Synonyms]
SynaptaMide
Dehydroepiandrosteron(DHEA)
Docosahexaenoyl Ethanolamide
N-Docosahexaenoylethanolamide
N-(2-Hydroxyethyl)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenamide
(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-Hydroxyethyl)docosa-4,7,10,13,16,19-hexaenamide
4,7,10,13,16,19-Docosahexaenamide, N-(2-hydroxyethyl)-, (4Z,7Z,10Z,13Z,16Z,19Z)- | [Molecular Formula]
C24H37NO2 | [MDL Number]
MFCD12912674 | [MOL File]
162758-94-3.mol | [Molecular Weight]
371.56 |
| Chemical Properties | Back Directory | [Boiling point ]
544.7±50.0 °C(Predicted) | [density ]
0.953±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO (up to 35 mg/ml) | [form ]
ethanol solution (5 mg/ml) | [pka]
14.47±0.10(Predicted) | [color ]
colorless to yellow | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored under inert gas at -80°C for up to 3 months. |
| Hazard Information | Back Directory | [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.1?Potently induces neuronal differentiation of neural stem cells.2?Promotes growth of cortical axons via modulation of hedgehog signaling.3?Binds to and activates orphan receptor GPR110, stimulating cAMP production at low nM concentrations.4?Reduces 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) | [storage]
Store at -20°C | [References]
1) Kim and Spector (2013),?Synaptamide, endocannabinoid-like derivative of docosahexaenoic acid with cannabinoid-independent function; Prostaglandins Leukot. Essent. Fatty Acids ,?88?121
2) Rashid?et al. (2013),?N-Docosahexaenoylethanolamide is a potent neurogenic factor for neural stem cell differentiation; J. Neurochem.,?125?869
3) Kharebava?et al.?(2015),?N-docosahexaenoylethanolamine regulates Hedgehog signaling and promotes growth of cortical axons; Biol. Open.,?4?1660
4) Lee?et al. (2016),?Orphan GPR110 (ADGRF1) targeted by N-docosahexaenoylethanolamine in development of neurons and cognitive function; Nat. Commun.,?7?13123
5) Park?et al. (2016),?N-docosahexaenoylethanolamine ameliorates LPS-induced neuroinflammation via cAMP/PKA-dependent signaling; J. Neuroinflammation,?13?284 |
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