Thyronamine

Thyronamine
Names
	Preferred IUPAC name 4-[4-(2-Aminoethyl)phenoxy]phenol
Identifiers
CAS Number	500-78-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL201896 ;
ChemSpider	2340781 ;
MeSH	thyronamine
PubChem CID	3083601;
CompTox Dashboard (EPA)	DTXSID60198174 ;
	InChI InChI=1S/C14H15NO2/c15-10-9-11-1-5-13(6-2-11)17-14-7-3-12(16)4-8-14/h1-8,16H,9-10,15H2 Key: OVUVNKDANCKDCK-UHFFFAOYSA-N ; InChI=1/C14H15NO2/c15-10-9-11-1-5-13(6-2-11)17-14-7-3-12(16)4-8-14/h1-8,16H,9-10,15H2 Key: OVUVNKDANCKDCK-UHFFFAOYAP;
	SMILES O(c1ccc(cc1)CCN)c2ccc(O)cc2;
Properties
Chemical formula	C14H15NO2
Molar mass	229.279 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Thyronamine refers both to a molecule, and to derivatives of that molecule: a family of decarboxylated and deiodinated metabolites of the thyroid hormones thyroxine (T4) and 3,5,3'-triiodothyronine (T3).

Types

The group includes:

Thyronamine (T0AM)
3-Iodothyronamine (T1AM), which is the most notable one as it is a trace amine found in the nervous system. It is a possible candidate for the natural ligand of the trace amine-associated receptor TAAR1 (TAR1), an intracellular G protein-coupled receptor^[1]
3,5-Diiodothyronamine (T2AM)
3,5,3'-Triiodothyronamine (T3AM)

^ Piehl S, Hoefig CS, Scanlan TS, Köhrle J (2011). "Thyronamines - Past, Present, and Future". Endocrine Reviews. 32 (1): 64–80. doi:10.1210/er.2009-0040. PMID 20880963.

Thyroid hormone metabolic intermediates
Tyrosine / iodotyrosine	3-Iodotyrosine Diiodotyrosine
Thyronine / iodothyronine	3'-Monoiodothyronine 3,3'-Diiodothyronine 3,5-Diiodothyronine 3,3',5-Triiodothyronine (T₃) 3,3',5'-Triiodothyronine (Reverse T₃) 3,5,3',5'-Tetraiodothyronine (Thyroxine, T₄)
/ iodothyronamine	3-Iodothyronamine 3,3',5-Triiodothyronamine
Iodothyroacetate / iodothyroacetic acid	Triiodothyroacetate (TRIAC)