Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 3-Iodothyronamine: Difference between pages

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| verifiedrevid = 477219003

| ImageSize = 230px

| ImageAlt = Skeletal formula of the 3-iodothyronamine

| ImageFile1 = 3-Iodothyronamine 3D ball.png

| ImageSize1 = 230px

| ImageAlt1 = Ball-and-stick model of the 3-iodothyronamine molecule

| PIN = 4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 9950514

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 712349-95-6

| SMILES = OC1=CC=C(OC2=C(I)C=C(CCN)C=C2)C=C1

|Section2={{Chembox Properties

| Formula = C₁₄H₁₄INO₂

| MolarMass = 355.17 g/mol

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'''3-Iodothyronamine''' ('''T₁AM''') is an [[endogenous]] [[thyronamine]]. T₁AM is a high-affinity [[ligand]] for the [[trace amine-associated receptor]] [[TAAR1]] (TAR1, TA1), a recently discovered [[G protein-coupled receptor]].<ref>{{cite journal |vauthors =Scanlan T, Suchland K, Hart M, Chiellini G, Huang Y, Kruzich P, Frascarelli S, Crossley D, Bunzow J, Ronca-Testoni S, Lin E, Hatton D, Zucchi R, Grandy D |title=3-Iodothyronamine is an endogenous and rapid-acting derivative of thyroid hormone |journal=Nat. Med. |volume=10 |issue=6 |pages=638–42 |year=2004 |pmid=15146179 |doi=10.1038/nm1051|s2cid=2389946 }}</ref><ref>{{cite journal |vauthors =Hart M, Suchland K, Miyakawa M, Bunzow J, Grandy D, Scanlan T |title=Trace amine-associated receptor agonists: synthesis and evaluation of thyronamines and related analogues |journal=J. Med. Chem. |volume=49 |issue=3 |pages=1101–12 |year=2006 |pmid=16451074 |doi=10.1021/jm0505718}}</ref> T₁AM is the most potent endogenous TAAR1 agonist yet discovered.<ref name="Wu">{{Cite journal

| vauthors = Wu SY, Green WL, Huang WS, Hays MT, Chopra IJ

| doi = 10.1089/thy.2005.15.943

| title = Alternate Pathways of Thyroid Hormone Metabolism

| journal = Thyroid

| volume = 15

| issue = 8

| pages = 943–958

| year = 2005

| pmid = 16131336

}}</ref> Activation of TAAR1 by T₁AM results in the production of large amounts of cAMP. This effect is coupled with decreased [[Thermoregulation|body temperature]] and [[cardiac output]].<ref>{{cite web |url=http://www.eurekalert.org/pub_releases/2004-05/ohs-ncm051404.php |title=New compound may act to keep thyroid activity in check |access-date=2008-05-30}}</ref> Wu ''et al.'' have pointed out that this relationship is not typical of the endocrine system, indicating that TAAR1 activity may not be coupled to G-proteins in some tissues, or that T₁AM may interact with other receptor subtypes.<ref name="Wu"/>

T₁AM may be part of a signaling pathway to modulate [[cardiac]] function, as the compound can induce negative [[inotropic]] effects and decrease [[cardiac output]].<ref>{{cite journal |vauthors =Chiellini G, Frascarelli S, Ghelardoni S, Carnicelli V, Tobias SC, Debarber A, Brogioni S, Ronca-Testoni S, Cerbai E, Grandy DK, Scanlan TS, Zucchi R |title=Cardiac effects of 3-iodothyronamine: a new aminergic system modulating cardiac function |journal= The FASEB Journal|volume= 21|issue= 7|pages= 1597–608|year=2007 |pmid=17284482 |doi=10.1096/fj.06-7474com|doi-access=free |s2cid=14015560 }}</ref>

==See also==

* [[O-Phenyl-3-iodotyramine|''O''-Phenyl-3-iodotyramine]]

* [[Trace amine]]

== References ==

{{Reflist}}

==External links==

* {{MeshName|3-iodothyronamine}}

{{Thyroid hormone intermediates}}

{{TAAR ligands}}

{{Phenethylamines}}

{{DEFAULTSORT:Iodothyronamine, 3-}}

[[Category:Biogenic amines]]

[[Category:Iodinated tyrosine derivatives]]

[[Category:Phenol ethers]]

[[Category:Phenethylamines]]

[[Category:Thyroid]]

[[Category:TAAR1 agonists]]

[[Category:Trace amines]]