3-Iodothyronamine
| 3-Iodothyronamine |
|
4-[4-(2-Amino-ethyl)-2-iodo-phenoxy]-phenol
|
|
|
| Identifiers |
| CAS number |
712349-95-6 |
| ChemSpider |
8126125 Y |
| Jmol-3D images |
Image 1
Image 2 |
-
OC1=CC=C(OC2=C(I)C=C(CCN)C=C2)C=C1
Ic2cc(ccc2Oc1ccc(O)cc1)CCN
|
-
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
|
| Properties |
| Molecular formula |
C14H14INO2 |
| Molar mass |
355.17 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
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.[1][2] T1AM is the most potent TAAR1 agonist yet discovered.[3] 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.[4] 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]
T1AM may be part of a signaling pathway to modulate cardiac function, as the compound can induce negative inotropic effects and decrease cardiac output.[5]
See also
External links
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. doi:10.1038/nm1051. 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. doi:10.1021/jm0505718. PMID 16451074.
- ^ a b Wu, S. Y.; Green, W. L.; Huang, W. S.; Hays, M. T.; Chopra, I. J. (2005). "Alternate Pathways of Thyroid Hormone Metabolism". Thyroid 15 (8): 943–958. doi:10.1089/thy.2005.15.943. PMID 16131336. edit
- ^ "New compound may act to keep thyroid activity in check". http://www.eurekalert.org/pub_releases/2004-05/ohs-ncm051404.php. Retrieved 2008-05-30.
- ^ 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". The FASEB journal : official publication of the Federation of American Societies for Experimental Biology 21 (7): 1597–608. doi:10.1096/fj.06-7474com. PMID 17284482.
|
|
|
| Tyrosine / iodotyrosine |
|
|
| Thyronine / iodothyronine |
|
|
| Thyronamine / iodothyronamine |
|
|
|
|
mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
|
k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
|
m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
|
|
|
|
|
noco(d)/cong/tumr, sysi/epon
|
proc, drug (A10/H1/H2/H3/H5)
|
|
|
|