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Merck
CN

91990

3,3′,5-Triiodo-L-thyronine

≥97.0% (sum of enantiomers, HPLC)

Synonym(s):

O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine, Liothyronine, T3

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About This Item

Empirical Formula (Hill Notation):
C15H12I3NO4
CAS Number:
6893-02-3
Molecular Weight:
650.97
EC Number:
229-999-3
UNSPSC Code:
51111800
MDL number:
MFCD00002593
Beilstein/REAXYS Number:
2710227

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InChI

1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1

InChI key

AUYYCJSJGJYCDS-LBPRGKRZSA-N

SMILES string

N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(O)=O

assay

≥97.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D +25±2°, c = 1% in ethanol/1 M HCl (2:1)

impurities

≤2% 3,5-diiodo thyronine, ≤2% thyroxine

mp

232-240 °C (dec.), 234-238 °C (lit.)

storage temp.

2-8°C

Other Notes

Review: Thyroid hormone action at the nuclear level

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

target_organs

Thyroid,Cardio-vascular system,Kidney

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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J H Oppenheimer
Annals of internal medicine, 102(3), 374-384 (1985-03-01)
Recent findings have led to a greater understanding of thyroid hormone action. The nuclear receptor for triiodothyronine is an integral component of a larger chromatin fragment. A stereospecific energy-dependent transport system appears responsible for translocation of triiodothyronine from cytosol to
J Himms-Hagen
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 4(11), 2890-2898 (1990-08-01)
Energy expenditure for thermogenesis in brown adipose tissue (BAT) serves either to maintain body temperature in the cold or to waste food energy. It has roles in thermal balance and energy balance, and when defective, is usually associated with obesity.
H Mizuma et al.
Circulation research, 88(3), 313-318 (2001-02-17)
Thyroid hormone has been reported to have significant effects on the peripheral vascular system, including relaxation of vascular smooth muscle cells and antiatherosclerotic effects. To exert its biological activity, thyroxine, which is a major secretory product of thyroid gland, needs
E Gunilla Stalenheim
Psychiatry research, 121(3), 281-291 (2003-12-17)
This study is a follow-up investigation of a forensic psychiatric sub-population 6-8 years after forensic psychiatric evaluation. The aim was to examine the long-term validity of biological markers of psychopathy and antisocial behavior over time. Data on criminal records were
R Calvo et al.
The Journal of clinical investigation, 86(3), 889-899 (1990-09-01)
To study the protective effects of maternal thyroxine (T4) and 3,5,3'-triiodothyronine (T3) in congenital hypothyroidism, we gave pregnant rats methimazole (MMI), an antithyroid drug that crosses the placenta, and infused them with three different doses of T4 or T3. The
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