147918-24-9

Basic information

• Product Name: N,O-Dibenzyl Serotonin
• Synonyms: N,O-Dibenzyl Serotonin
• CAS NO: 147918-24-9
• Molecular Formula: C₂₄H₂₄N₂O
• Molecular Weight: 355.45222
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Neurochemicals
• Mol File: 147918-24-9.mol

Chemical Properties

• Appearance: /
• Solubility: Ethyl Acetate, Methanol
• CAS DataBase Reference: N,O-Dibenzyl Serotonin(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-Dibenzyl Serotonin(147918-24-9)
• EPA Substance Registry System: N,O-Dibenzyl Serotonin(147918-24-9)

Safety Data

• Hazardous Substances Data: 147918-24-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,O-Dibenzyl Serotonin is used as an intermediate compound for the synthesis of various serotonin-based drugs. Its application is crucial in the development of medications targeting neurological and psychiatric disorders, such as depression, anxiety, and migraines. The dibenzyl protection group allows for selective functionalization and modification of the serotonin molecule, enabling the creation of more potent and selective drugs.
Used in Research and Development:
In the field of research, N,O-Dibenzyl Serotonin serves as a valuable tool for studying the structure, function, and interactions of serotonin in biological systems. Its protected structure allows for controlled and specific modifications, facilitating the investigation of serotonin's role in various physiological processes and the development of novel therapeutic strategies.
Used in Drug Delivery Systems:
Similar to gallotannin, N,O-Dibenzyl Serotonin can be incorporated into drug delivery systems to enhance its bioavailability, stability, and therapeutic efficacy. By employing various carriers, such as organic and metallic nanoparticles, the compound can be effectively delivered to target cells and tissues, improving its overall performance in treating specific conditions.

Upstream product

• 102754-41-6 N-Benzyl-2-<5-(benzyloxy)-3-indolyl>glyoxylamid 
• 1215-59-4 5-benzyloxy-1H-indole 
• 22424-61-9 2-[5-(benzyloxy)-1H-indol-3-yl]-2-oxoacetyl chloride 
• 104-63-2 N-Benzylethanolamine 

Downstream Products

• 147918-26-1 2-Benzyl-6-(benzyloxy)-1-(2-<(2,4,10-trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethyl>)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol 
• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 
• 147918-28-3 6-Benzyloxy-1-(2-<(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethyl>)-9H-pyrido<3,4-b>indol 

Relevant articles and documents

Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin

Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.

Synthesis of Manzamine C, Infractine and 6-Hydroxyinfractine

Manzamine C (1), a β-carboline alkaloid with antitumor activity isolated from the marine sponge Haliclona sp. was synthesized.The dilithium derivative of 5-hexynoic acid (6) was alkylated with 7 to give after esterification the methyl 10-hydroxy-5-decynoate (8).The tosylate of 8 was converted into the azide 9 which could be selectively hydrogenated with Lindlar palladium catalyst to give the amino ester 10.Saponification of 10 and acylation with (Boc)2O yielded 11, which was converted with pentafluorophenol into 12.Removal of the Boc group in 12 gave an amino ester as intermediate, which cyclized immediately under high dilution conditions to give the lactam 13 in high yield.Reduction of 13 with LiAlH4 produced the macrocyclic amine 4.The β-carboline part of 1 was prepared by condensation of N-benzyltryptamine 14 with the formylacetic acid equivalent 15 to give 16.Dehydrogenation of 16 with Pd-on-carbon catalyst led to the orthoester 17, which could be converted into the methyl ester 5 in high overall yield.The 4-(dimethylamino)pyridine-catalyzed substitution of the methyl ester function in 5 by the amine 4 gave the amide 29.The analogous reaction of 5 with pyrrolidine or with azacyclotridecane yielded 30 and 31.Reduction of these three amides with LiAlH4 produced 1, 2 and 3.The spectroscopic properties of 1 were identical with those of natural manzamine C. - Condensation of 14 or N-benzyl-5-(benzyloxy)tryptamine (19) with aldehyde 18 yielded the products 20 and 21, which could be dehydrogenated to furnish 22 and 23.From these the methyl esters 24 and 25 with properties identical to those of the known β-carboline alkaloids infractine and 6-hydroxyinfractine could be obtained.