3-Iodothyronamine

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. T1AM is the most potent endogenous TAAR1 agonist yet discovered. Activation of TAAR1 by T1AM results in the production of large amounts of cAMP. This effect is coupled with decreased body temperature and cardiac output. 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.

3-Iodothyronamine
Names
Preferred IUPAC name
4-[4-(2-Aminoethyl)-2-iodophenoxy]phenol
Other names
T1AM
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.211.501
  • InChI=1S/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2 Y
    Key: XIINYOJWNGOUPF-UHFFFAOYSA-N Y
  • InChI=1/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2
    Key: XIINYOJWNGOUPF-UHFFFAOYAJ
  • OC1=CC=C(OC2=C(I)C=C(CCN)C=C2)C=C1
  • Ic2cc(ccc2Oc1ccc(O)cc1)CCN
Properties
C14H14INO2
Molar mass 355.17 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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

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