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3-Iodothyronamine

3-Iodothyronamine

IUPAC name	4-[4-(2-Amino-ethyl)-2-iodo-phenoxy]-phenol
Other names	T₁AM
Identifiers
CAS number	712349-95-6
SMILES	OC1=CC=C(OC2=C(I)C=C(CCN)C=C2)C=C1
Properties
Molecular formula	C₁₄H₁₄INO₂
Molar mass	355.17 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

3-iodothyronamine (T₁AM) is an endogenous thyronamine. T₁AM is a high-affinity ligand for the trace amine-associated receptor TAAR1 (TAR1, TA1), a G protein-coupled receptor.^[1] ^[2] In rodents, T₁AM causes a rapid drop in body temperature when injected.

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T₁AM may be part of a signaling pathway to modulate cardiac function as the compound can induce negative inotropic effects and decrease cardiac output.^[3]

References

^ 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 (2004). "3-Iodothyronamine is an endogenous and rapid-acting derivative of thyroid hormone". Nat. Med. 10 (6): 638-42. PMID 15146179.
^ Hart M, Suchland K, Miyakawa M, Bunzow J, Grandy D, Scanlan T (2006). "Trace amine-associated receptor agonists: synthesis and evaluation of thyronamines and related analogues". J. Med. Chem. 49 (3): 1101-12. PMID 16451074.
^ 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. (2007). "Cardiac effects of 3-iodothyronamine: a new aminergic system modulating cardiac function". PMID 17284482.