Reverse triiodothyronine

Reverse triiodothyronine

Names
IUPAC name (2S)-2-Amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3-iodophenyl]propanoic acid
Identifiers
CAS Number	5817-39-0
3D model (Jmol)	Interactive image
ChEBI	CHEBI:11684
ChemSpider	559294
ECHA InfoCard	100.150.134
IUPHAR/BPS	2636
KEGG	C07639
MeSH	Reverse+triiodothyronine
PubChem	22069
InChI InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1 Key: HZCBWYNLGPIQRK-LBPRGKRZSA-N InChI=1/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1 Key: HZCBWYNLGPIQRK-LBPRGKRZBV
SMILES C1=CC(=C(C=C1C[C@@H](C(=O)O)N)I)OC2=CC(=C(C(=C2)I)O)I
Properties
Chemical formula	C15H12I3NO4
Molar mass	650.974
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reverse triiodothyronine (3,3’,5’-triiodothyronine, reverse T₃, or rT₃) is an isomer of triiodothyronine (3,5,3’ triiodothyronine, T₃).

Reverse T₃ is the third-most common iodothyronine the thyroid gland releases into the bloodstream, of which 0.9% is rT₃; tetraiodothyronine (levothyroxine, T₄) constitutes 90% and T₃ is 9%. However, 95% of rT₃ in human blood is made elsewhere in the body, as enzymes remove a particular iodine atom from T₄.^[1]

The production of hormone by the thyroid gland is controlled by the hypothalamus and pituitary gland. The physiological activity of thyroid hormone is regulated by a system of enzymes that activate, inactivate or simply discard the prohormone T₄ and in turn functionally modify T₃ and rT₃. These enzymes operate under complex direction of systems including neurotransmitters, hormones, markers of metabolism and immunological signals.

The levels of rT3 increase in conditions such as euthyroid sick syndrome because its clearance decreases while its production stays the same. The decreased clearance is possibly from lower 5'-deiodinase activity in the peripheral tissue or decreased liver uptake of rT3.^[2]

Reactions

Synthesis of Reverse T₃ from T₄ via deiodination. Synthesis of T₃ and T₂ is also shown.

References

1. Chopra IJ (July 1976). "An assessment of daily production and significance of thyroidal secretion of 3, 3', 5'-triiodothyronine (reverse T3) in man". J. Clin. Invest. 58 (1): 32–40. doi:10.1172/JCI108456. PMC 333152. PMID 932209.
2. Euthyroid Sick Syndrome at eMedicine

External links

• Triiodothyronine, Reverse at the US National Library of Medicine Medical Subject Headings (MeSH)