25I-Nboh

Base Information

• Chemical Name: 25I-Nboh
• CAS No.: 919797-20-9
• Molecular Formula: C₁₇H₂₀INO₃
• Molecular Weight: 413.255
• UNII: W9G4BGW8K4
• DSSTox Substance ID: DTXSID80433993
• Nikkaji Number: J3.667.566G
• Wikipedia: 25I-NBOH
• Wikidata: Q4632139
• Mol file: 919797-20-9.mol

Synonyms:25I-NBOH;N-(2-hydroxybenzyl)-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-aminium

Chemical Property of 25I-Nboh

Chemical Property:

• Boiling Point: 497.0±45.0 °C(Predicted)
• PKA: 10.37±0.30(Predicted)
• PSA: 50.72000
• Density: 1.493±0.06 g/cm3(Predicted)
• LogP: 3.73720
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 413.04879
• Heavy Atom Count: 22
• Complexity: 318

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1CCNCC2=CC=CC=C2O)OC)I

Technology Process of 25I-Nboh

There total 12 articles about 25I-Nboh which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 19.0%

C17H18INO3 → 2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol (919797-20-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 0.5h;

DOI:10.1016/j.tet.2017.09.024

Reference yield:

N-(tert-butoxycarbonyl)-N-(2-hydroxybenzyl)-2-(4-iodo-2-hydroxy-5-methoxyphenyl)ethylamine (1043869-10-8) + methyl iodide (74-88-4) → 2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol (919797-20-9) + 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine hydrochloride (1043868-97-8) + 5-iodo-4-methoxy-2-(2-((2-methoxybenzyl)amino)ethyl)phenol (1043869-18-6)

Guidance literature:

N-(tert-butoxycarbonyl)-N-(2-hydroxybenzyl)-2-(4-iodo-2-hydroxy-5-methoxyphenyl)ethylamine; methyl iodide; With sodium hydride; In N,N-dimethyl-formamide;

With hydrogenchloride; In methanol; at 20 ℃; for 12h; Further stages.;

DOI:10.1016/j.bmc.2008.04.050

Reference yield:

4-iodo-2,5-dimethoxy-β-phenethylamine hydrochloride (64584-32-3) + salicylaldehyde (90-02-8) → 2-(((4-iodo-2,5-dimethoxyphenethyl)amino)methyl)phenol (919797-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / ethanol / 20 °C

2: sodium tetrahydroborate / ethanol / 0.5 h / 20 °C

With sodium tetrahydroborate; triethylamine; In ethanol;

DOI:10.1021/cn400216u

upstream raw materials:

N-(tert-butoxycarbonyl)-N-(2-hydroxybenzyl)-2-(4-iodo-2-hydroxy-5-methoxyphenyl)ethylamine

methyl iodide

4-iodo-2,5-dimethoxy-β-phenethylamine hydrochloride

salicylaldehyde

Refernces

• 1、 Wu, Xiongyu,Eriksson, Caroline,Wohlfarth, Ariane,Wallgren, Jakob,Kronstrand, Robert,Josefsson, Martin,Dahlén, Johan,Konradsson, Peter. "Synthesis and identification of metabolite biomarkers of 25C-NBOMe and 25I-NBOMe". . p. 6393 - 6400. Retrieved 2017/10/16.
• 2、 Nichols, David E.,Frescas, Stewart P.,Chemel, Benjamin R.,Rehder, Kenneth S.,Zhong, Desong,Lewin, Anita H.. "High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A high-affinity 5-HT2A receptor-selective agonist radioligand". . p. 6116 - 6123. Retrieved 2008/12/21.