Синаптамид

Description

Synaptamide is the ethanolamide of docosahexaenoic acid, systematically N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine. The molecule is formed by combining docosahexaenoic acid (DHA) with ethanolamine through an amide bond and belongs to the class of N-acylethanolamines with a composition of 22:6. According to the functional classification, it is an endocannabinoid, structurally similar to N-arachidonoylethanolamine - anandamide; the difference lies in the fatty acid part: for anandamide it is arachidonic acid 20:4, for synaptamide it is docosahexaenoic acid 22:6.

Basic Attributes

• CAS No: 162758-94-3
• Chemical formula: C24H37NO2
• Molecular weight: 371.561
• Exact card weight: 371.56
• DSSTox ID: DTXSID50678596
• PSA specifications: 49.3

Physico-chemical properties

• Appearance: colorless to yellow
• Storage conditions: −20 °C
• Collision cross section: 191.88 Ų for [M+H]⁺ ion, CCS TIMS type, single field calibration method

The six double bonds in the chain make the compound extremely sensitive to oxidation - which is why the recommended storage temperature is −20 °C, rather than the usual 2–8 °C. Yellowing of the product is a sign that oxidation has begun. The given exact mass of 371.56 coincides with the rounded molecular mass and does not correspond to the monoisotopic mass of the formula C24H37NO2; during mass spectrometry it should be recalculated. The collision cross section value of 191.88 Ų was obtained by TIMS and is useful for identity confirmation in ion mobility schemes.

Mechanism of action

Synaptamide is an endogenous metabolite of docosahexaenoic acid that actively stimulates neurogenesis, neuritogenesis and synaptogenesis. Its receptor is the G-protein coupled adhesion receptor, the orphan GPR110, also known as ADGRF1.

• Binding occurs through the interface of the GAIN receptor subdomains, key contacts are formed with residues Q511, N512 and Y513
• Binding causes an intracellular conformational change near the sixth transmembrane segment (TM6), which triggers signal transduction
• Signaling pathway cAMP-dependent; cyclic AMP production is activated in the low nanomolar concentration range
• The specificity of the interaction was confirmed by methods of mass spectrometric proteomics and cellular fluorescent tracking with chemical analogues of synaptamide

The cause-and-effect relationship has been established genetically: disruption of binding or knockout of the GPR110 gene completely abolishes the biological effect of synaptamide, and overexpression of the receptor enhances it. GPR110 expression is high in the fetal brain and declines rapidly after birth. GPR110 knockout mice exhibit severe impairments in object recognition and spatial memory. The anti-inflammatory effect of N-docosahexaenoyl ethanolamine is realized through the same receptor.

Scope of application

• research reagent in neuroscience: studying neuronal development, neurite growth and synapse formation
• GPR110 (ADGRF1) agonist in pharmacological studies of G-protein coupled adhesion receptors
• object of work on lipid mediators and the mechanisms of action of docosahexaenoic acid
• analytical standard for the determination of N-acylethanolamines in biological samples

Safety Information

• WGK Germany: 3
• Harmonized phrases H and P, labels, hazard class codes and transport classification are not given on the card - check with the batch’s safety data sheet

Storage and handling

Mandatory storage mode is minus 20 °C. The polyunsaturated chain with six double bonds is oxidized by atmospheric oxygen: the product should be stored in an inert atmosphere or in hermetically sealed ampoules, protected from light and not subjected to repeated freeze-thaw cycles. Solutions in organic solvents are prepared immediately before the experiment and stored under nitrogen or argon. Class WGK Germany 3 excludes discharge into sewerage. Carry out work under a hood, wearing gloves and safety glasses.