52055-23-9

Basic information

• Product Name: 5-Benzyloxytryptamine hydrochloride
• Synonyms: 2-(5-Phenylmethoxy-1H-indol-3-yl)ethanamine hydrochloride;2-[5-(benzyloxy)-1H-indol-3-yl]ethanamine;5-Benzyloxytryptamine hydrochloride,98%;5-(phenylmethoxy)indole-3-ethanamine monohydrochloride;2-(5-benzoxy-1H-indol-3-yl)ethylamine hydrochloride;2-(5-benzyloxy-1H-indol-3-yl)ethanamine hydrochloride;2-[5-(benzyloxy)-1H-indol-3-yl]ethanamine hydrochloride;3-(2-AMINOETHYL)-5-BENZYLOXYINDOLE HYDROCHLORIDE
• CAS NO: 52055-23-9
• Molecular Formula: C₁₇H₁₈N₂O*ClH
• Molecular Weight: 302.8
• EINECS: 257-626-4
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles;Tryptamines
• Mol File: 52055-23-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 260-263 °C(lit.)
• Boiling Point: 480.5 °C at 760 mmHg
• Flash Point: 244.4 °C
• Appearance: White to yellow to beige/Crystalline Powder
• Vapor Pressure: 2.15E-09mmHg at 25°C
• Storage Temp.: -20°C
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-Benzyloxytryptamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzyloxytryptamine hydrochloride(52055-23-9)
• EPA Substance Registry System: 5-Benzyloxytryptamine hydrochloride(52055-23-9)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37
• Safety Statements: 36/37-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52055-23-9(Hazardous Substances Data)

Usage

Chemical Properties

white to yellowish to beige crystalline powder

Uses

Different sources of media describe the Uses of 52055-23-9 differently. You can refer to the following data:
1. Reactant for preparation of:Indole alkaloid-based compounds for drug discoverySerotonin 5-HT6 receptor ligands
2. 5-benzyloxytryptamine hydrochloride is a useful reactant for the preparation of thioacetylated pseudopeptides.

InChI:InChI=1/C17H18N2O/c18-9-8-14-11-19-17-7-6-15(10-16(14)17)20-12-13-4-2-1-3-5-13/h1-7,10-11,19H,8-9,12,18H2/p+1

Upstream product

• 53157-47-4 [2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 153-98-0 serotonin hydrochloride 
• 53157-48-5 tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate 
• 5933-28-8 5-benzyloxyindole-3-acetamide 

Downstream Products

• 600121-84-4 6-benzyloxy-1-furan-2-yl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester 
• 224180-91-0 N-[2-(5-Benzyloxyindol-3-yl)ethyl] butanamide 
• 1450838-12-6 (2S)-2-benzyl 6-ethanethioamido-1-oxo-1-[2-(5-benzyloxy-1H-indol-3yl)ethylamino]hexan-2-ylcarbamate 
• 1262007-29-3 2-(6-(2,4-bis(trifluoromethyl)benzyloxy)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetic acid 
• 1262008-17-2 2-(6-(2,4-bis(trifluoromethyl)benzyloxy)-2-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetic acid 
• 1262008-16-1 tert-butyl 6-(2,4-bis(trifluoromethyl)benzyloxy)-1-(2-methoxy-2-oxoethyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 
• 1262008-10-5 tert-butyl 1-(2-methoxy-2-oxoethyl)-6-(4-(trifluoromethyl)benzyloxy)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 
• 1262007-40-8 2-(6-(3-(trifluoromethoxy)benzyloxy)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetic acid trifluoroacetate 

Relevant articles and documents

Optimization of 5-hydroxytryptamines as dual function inhibitors targeting phospholipase A2 and leukotriene A4 hydrolase

Dual function inhibitors targeting phospholipase A2 (PLA 2) and leukotriene A4 hydrolase (LTA4H) may balance the arachidonic acid (AA) metabolic network and be used as new anti-inflammatory drugs. In previous study, we discovered multi-target drugs towards the AA metabolic network, among which a dual-target inhibitor (JMC08-4) for human nonpancreatic secretory phospholipase A2 (hnps-PLA 2) and human leukotriene A4 hydrolase (LTA4H-h) was found. Based on the structure of compound JMC08-4, new dual-target inhibitors were designed assisted by molecular docking. In this report, a series of 5-hydroxytryptamine compounds were synthesized; and most of these title compounds showed more potent inhibitory activity than compound JMC08-4 in the in vitro bioassay against these two enzymes. The best one inhibited hnps-PLA 2 and LTA4H-h with IC50 values of 9.2 ± 0.5 μM and 2.4 ± 1.4 μM, respectively.

Brain-specific drug delivery

The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are: (a) compounds of the formula wherein [D] is a centrally acting drug species, and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier, with the proviso that when [DHC] is STR1 wherein R is lower alkyl or benzyl and [D] is a drug species containing a single NH2 or OH functional group, the single OH group when present being a primary or secondary OH group, said drug species being linked directly through said NH2 or OH functional group to the carbonyl function of [DHC], then [D] must be other than a sympathetic stimulant, steroid sex hormone or long chain alkanol; and (b) non-toxic pharmaceutically acceptable salts of compounds of formula (I) wherein [D] is a centrally acting drug species and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine pyridinium salt redox carrier. The corresponding ionic pyridinium salt type drug/carrier entities [D-QC]+ Y- are also disclosed.