788824-64-6

Basic information

• Product Name: 4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol Hydrochloride
• Synonyms: 3-Iodothyronamine Hydrochloride;4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol Hydrochloride
• CAS NO: 788824-64-6
• Molecular Formula: C14H15ClINO2
• Molecular Weight: 0
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 788824-64-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 209-211°C
• Appearance: /
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• CAS DataBase Reference: 4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol Hydrochloride(788824-64-6)
• EPA Substance Registry System: 4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol Hydrochloride(788824-64-6)

Safety Data

• Hazardous Substances Data: 788824-64-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 788824-64-6 differently. You can refer to the following data:
1. 3-Iodothyronamine is a novel metabolite of thyroid hormone (TH). 3-Iodothyronamine (T1AM) take in rodents.
2. A novel metabolite of thyroid hormone (TH). 3-Iodothyronamine (T1AM) is an endogenous and rapid-acting derivative of thyroid hormone.

Upstream product

• 1304495-16-6 C₁₄H₁₀INO₂ 
• 1304495-14-4 C₁₅H₁₂N₂O₄ 
• 643090-93-1 (4-((triisopropylsilyl)oxy)phenyl)boronic acid 
• 193966-77-7 4-bromo-1-(triisopropylsilyloxy)benzene 
• 64318-28-1 N-t-butoxycarbonyl-tyramine 
• 106-41-2 4-bromo-phenol 
• 51-67-2 tyrosamine 
• 788824-53-3 N-t-butoxycarbonyl-O-triisopropylsilyl-3-iodothyronamine 
• 788824-50-0 [2-(4-hydroxy-3-iodo-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 788824-56-6 N-t-butoxycarbonyl-3-iodothyronamine 

Relevant articles and documents

A new efficient synthetic method for 3-iodothyronamine involving sonication and its potent hypothermic efficacy

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Trace amine-associated receptor agonists: Synthesis and evaluation of thyronamines and related analogues

We have previously shown that several thyronamines, decarboxylated and deiodinated metabolites of the thyroid hormone, potently activate an orphan G protein-coupled receptor in vitro (TAAR1) and induced hypothermia in vivo on a rapid time scale [Scanlan, T. S.; Suchland, K. L.; Hart, M. E.; Chiellini, G.; Huang, Y.; Kruzich, P. J.; Frascarelli, S.; Crossley, D. A.; Bunzow, J. R.; Ronca-Testoni, S.; Lin, E. T.; Hatton, D.; Zucchi, R.; Grandy, D. K. 3-Iodothyronamine is an endogenous and rapid-acting derivative of thyroid hormone. Nat. Med. 2004, 10 (6), 638-642]. Herein, we report the synthesis of these thyronamines. Additionally, a large number of thyroamine derivatives were synthesized in an effort to understand the molecular basis of TAAR1 activation and hypothermia induction. Several derivatives were found to potently activate both rTAAR1 and mTAAR1 in vitro (compounds 77, 85, 91, and 92). When administered to mice at a 50 mg/kg dose, these derivatives all induced significant hypothermia within 60 min and exhibited a hypothermic induction profile analogous to 3-iodothyronamine (1, T1AM) except 91, which proved to be more efficacious. On the basis of this result, a dose-dependent profile for 91 was generated and an ED50 of 30 μmol/kg was calculated. Compound 91 proved to be more potent than T1AM for TAAR1 activation and exhibits increased potency and efficacy for hypothermia induction. These data further strengthen the pharmacological correlation linking TAAR1 activation by thyronamines and hypothermia induction in mice.