ChemicalBook CAS DataBase List 5-Hydroxytryptamine

5-Hydroxytryptamine synthesis

14synthesis methods

Product Name:5-Hydroxytryptamine
CAS Number:50-67-9
Molecular formula:C10H12N2O
Molecular Weight:176.22

Serotonin is synthetized in two steps from tryptophan, an essential amino acid acquired from food. The first and limiting enzymatic step is hydroxylation by tryptophan-hydroxylase (TPH) to produce 5-hydroxytryptophan. The TPH1 isoform is found in EC cells, and the TPH2 isoform is located in central and enteric neurons. The next step is conversion to 5-hydroxytryptamine by an aromatic L-amino acid decarboxylase. 5-HT is then packaged into vesicles by the vesicular monoamine transporter (VMAT). The sequestration of 5-HT to vesicles in the cytoplasm prevents rapid degradation by monoamine oxidase (MAO). MAO breaks down 5-HT to form 5-hydroxyindoleacetic acid (5-HIAA), which is mainly excreted in urine. The SERT relocates 5-HT into presynaptic terminals in the CNS, and into platelets (the main store of 5-HT). SERT is expressed in pulmonary and peripheral blood vessels, as well as in the GI tract.

Serotonin biosynthesis

147918-24-9
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50-67-9
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Yield:50-67-9 100%

Reaction Conditions:

with palladium 10% on activated carbon;ammonium formate in methanol at 70; for 0.75 h;Inert atmosphere;

Steps:

4.2.3 _{RRN 82,83,84}General procedure for the hydrogenolysis for the synthesis of the natural products
General procedure: Psilocin, Bufotenin and Serotonin. To a stirred suspension of the suitable tryptamine (0.25mmol) and an equal weight of 10% Pd-C in dry methanol (7mL), anhydrous ammonium formate (71mg, 1.125mmol) was added in a single portion under N₂. The resulting reaction mixture was stirred at 70°C for 45min. The solution was filtered through a pad of Celite, the solvent was removed under reduce pressure and the residue was purified by flash column chromatography on silica gel (DCM:MeOH 9:1 and 1% of TEA) to give the corresponding natural product in quantitative yield.

References:

Bartolucci, Silvia;Mari, Michele;Di Gregorio, Giovanni;Piersanti, Giovanni [Tetrahedron,2016,vol. 72,# 18,p. 2233 - 2238]

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608-07-1 Synthesis