53157-48-5

Basic information

• Product Name: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole
• Synonyms: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole;N-tert-Butyloxycarbonyl Serotonin;tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate;tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate, 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole, 3-[2-(tert-butoxycarbonylamino)ethyl]-5-hydroxyindole, Serotonin (N-Boc), N-Boc-serotonin, 3-ethyl>-1H-indol-5-ol, tert-butyl (2-(5-hydroxy-1H-indol-3-yl)ethyl)carbamate
• CAS NO: 53157-48-5
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276
• Product Categories: Aromatics, Glucuronides, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 53157-48-5.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Dichloromethane, DMSO (Slightly), Ethyl Acetate, Methanol
• CAS DataBase Reference: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole(53157-48-5)
• EPA Substance Registry System: 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole(53157-48-5)

Safety Data

• Hazardous Substances Data: 53157-48-5(Hazardous Substances Data)

Usage

Description

3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole, also known as N-tert-Butyloxycarbonyl Serotonin, is a chemical compound derived from the monoamine neurotransmitter serotonin. It is characterized by the presence of a t-butyloxycarbonyl (Boc) protecting group, which is commonly used in organic synthesis to protect amino groups. 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is significant in the field of medicinal chemistry due to its potential applications in the development of protein kinase inhibitors and receptor agonists.

Uses

Used in Pharmaceutical Industry:
3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is used as a key intermediate in the synthesis of protein kinase inhibitors and receptor agonists for the pharmaceutical industry. The application reason is that this compound serves as a building block for the development of new drugs targeting various diseases, including neurological disorders and cancer.
Used in Research and Development:
In the research and development sector, 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is used as a valuable tool for studying the structure-activity relationships of serotonin and its analogs. The application reason is to gain insights into the molecular mechanisms underlying the biological activities of these compounds, which can ultimately lead to the design of more effective therapeutic agents.
Used in Chemical Synthesis:
3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole is also used as a protected amino acid in various chemical synthesis processes. The application reason is that the Boc group provides a stable and easily removable protecting group for the amino functionality, allowing for the selective protection of amino groups during multi-step synthesis.

Upstream product

• 61-47-2 serotonin creatinine sulfate monohydrate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 584-08-7 potassium carbonate 
• 153-98-0 serotonin hydrochloride 
• 21591-86-6 5-hydroxytryptamine hydrochloride 
• 34619-03-9 tert-butyldicarbonate 
• 119768-45-5 (S)-2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoic acid 
• 50-67-9 3-(2-aminoethyl)-1H-indol-5-ol 
• 971-74-4 serotonin creatinine sulfate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 165751-26-8 (2-{5-[2-Oxo-2-(4-phenyl-piperazin-1-yl)-ethoxy]-1H-indol-3-yl}-ethyl)-carbamic acid tert-butyl ester 
• 947766-67-8 C₂₃H₂₆N₂O₄ 
• 1228827-54-0 tert-butyl 2-{5-[2-(4-(methoxymethoxy)phenyl)ethoxy]-1H-indole-3-yl}ethylcarbamate 
• 1432472-66-6 2-(5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-1H-indol-3-yl)ethanamine hydrochloride 
• 1432473-10-3 C₂₂H₃₄N₂O₆ 
• 1373764-85-2 C₂₇H₂₆N₂O₂ 
• 1373764-86-3 6-hydroxy-1-methyl-N-phenylacetyl-1,3,4,9-tetrahydro-β-carboline 
• 20776-45-8 5-benzyloxytryptamine 
• 17952-78-2 6-(benzyloxy)-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 53157-47-4 [2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 153-98-0 serotonin hydrochloride 
• 1422539-10-3 C₂₄H₂₃N₃O₅*ClH 
• 1422539-06-7 C₂₉H₃₁N₃O₇ 
• 1422539-03-4 C₂₈H₃₀N₂O₄ 

Relevant articles and documents

Structure-activity relationship of serotonin derived tocopherol lipids

Tocopherol-based lipids are widely used for nucleic acid delivery. Using tocopherol molecules, we designed and synthesized 5-HT functionalized lipids by tethering 5-hydroxytryptamine (5-HT), a small molecule ligand as the head group to a natural amphiphilic molecule namely α-tocopherol (Vitamin E). This is with the aim of delivering nucleic acids specifically into cells expressing the serotonin receptors (5-hydroxytryptamine[5-HT]) which are abundant in the central nervous system. In order to achieve target recognition, we adopted an approach wherein two structurally different lipid molecules having serotonin as the head group was conjugated to tocopherol via different linkers thus generating lipids with either free –NH2 or –OH moiety. The corresponding lipids designated as Lipid A (Tocopheryl carbonate serotonin-NH2) and Lipid B (Tocopheryl 2-hydroxy propyl ammonium serotonin-OH), were formulated with co-lipids 1,2-dioleoyl-sn-glycero-3-phosphatidyl-ethanolamine (DOPE) and 1,2-dioleoyl-sn-glycero-sn-3-phosphatidylcholine (DOPC) and evaluated for their ability to deliver plasmid DNA through reporter gene expression assays in vitro. Furthermore, the physicochemical characteristics and cellular interactions of the formulations were examined using serotonin-receptor enriched cells in order to distinguish the structural and functional attributes of both lipids. Cell-based gene expression studies reveal that in comparison to Lipid A, a formulation of Lipid B prepared with DOPE as the co-lipid, contributes to efficient uptake leading to significant enhancement in transfection. Specific interactions explored by molecular docking studies suggests the role of the hydroxyl moiety and the enantiospecific significance of serotonin- conjugated tocopherol lipids in recognizing these receptors thus signifying a promising lipid-based approach to target the serotonin receptors in the central nervous system.

Method for preparing 5-hydroxytryptamine hydrochloride by utilizing enzymatic fermentation liquor containing 5-hydroxytryptamine

The invention discloses a method for preparing 5-hydroxytryptamine hydrochloride from 5-hydroxytryptamine-containing enzymatic fermentation liquor, and relates to the technical field of 5-hydroxytryptamine extraction. The method comprises the following steps: concentrating 5-hydroxytryptamine-containing enzymatic fermentation liquor under reduced pressure, mixing the concentrated 5-hydroxytryptamine-containing enzymatic fermentation liquor with an organic solvent, sequentially dropwise adding triethylamine and BOC anhydride at low temperature, heating to 20-25 DEG C after dropwise adding is finished, reacting to obtain an N-BOC-5-hydroxytryptamine reaction solution, adding ethyl acetate, and extracting to obtain an ethyl acetate organic phase; adding ethyl acetate containing hydrochloric acid into the ethyl acetate organic phase for reaction, and performing suction filtration after the reaction is finished to obtain a 5-hydroxytryptamine hydrochloride crude product; and further purifying the obtained 5-hydroxytryptamine hydrochloride crude product to obtain 5-hydroxytryptamine hydrochloride. According t o the invention, high-purity 5-hydroxytryptamine hydrochloride is prepared by optimizing the method for purifying 5-hydroxytryptamine in an enzymatic fermentation liquor, so that the current situation that 5-hydroxytryptamine hydrochloride is difficult to prepare by simply extracting serotonin in the enzymatic fermentation liquor is changed.

Nanosensor for Sensitive Detection of the New Psychedelic Drug 25I-NBOMe

This work reports the synthesis, characterization, and sensing behavior of a hybrid nanodevice for the detection of the potent abuse drug 25I-NBOMe. The system is based on mesoporous silica nanoparticles, loaded with a fluorescent dye, functionalized with