ContaminantDB: Liothyronine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:15:14 UTC

Update Date

2026-04-05 16:29:08 UTC

Accession Number

CHEM003716

Identification

Common Name

Liothyronine

Class

Small Molecule

Description

The L-triiodothyronine (T₃, liothyronine) thyroid hormone is normally synthesized and secreted by the thyroid gland in much smaller quantities than L-tetraiodothyronine (T₄, levothyroxine, L-thyroxine). Most T3 is derived from peripheral monodeiodination of T4 at the 5 position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Animal Toxin
Drug
Ether
Food Toxin
Hormone Replacement Agent
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5,3'-Triiodo-L-thyronine	ChEBI
3,5,3'-Triiodothyronine	ChEBI
3,5,3'TRIIODOTHYRONINE	ChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine	ChEBI
L-3,5,3'-Triiodothyronine	ChEBI
L-T3	ChEBI
Liothyroninum	ChEBI
Liotironina	ChEBI
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine	ChEBI
T3	ChEBI
Tertroxin	ChEBI
Tresitope	ChEBI
Triiodothyronine	ChEBI
3,3',5-Triiodo-L-thyronine	Kegg
Thyrolar	Kegg
3,3',5-Triiodothyronine	HMDB
Cytomel	HMDB
T3 Thyroid hormone	HMDB
Thyroid hormone, T3	HMDB
Liothyronine sodium	HMDB
3,3',5'-Triiodo-L-thyronine	HMDB
3,3',5'-Triiodothyronine	HMDB
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine	HMDB
Cyronine	HMDB
L-3,3',5-Triiodo-thyronine	HMDB
L-3,3',5-Triiodothyronine	HMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine	HMDB
L-Liothyronine	HMDB
L-Triiodothyronine	HMDB
Liothyronin	HMDB
Triiodo-L-thyronine	HMDB

Chemical Formula

C₁₅H₁₂I₃NO₄

Average Molecular Mass

650.974 g/mol

Monoisotopic Mass

650.790 g/mol

CAS Registry Number

6893-02-3

IUPAC Name

(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

Traditional Name

liothyronine

SMILES

N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Diphenylether
Diaryl ether
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Phenoxy compound
2-iodophenol
2-halophenol
Phenol ether
Iodobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Aralkylamine
Aryl iodide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Amino acid
Ether
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

iodothyronine (CHEBI:18258 )
iodophenol (CHEBI:18258 )
2-halophenol (CHEBI:18258 )
thyroxine (C02465 )
Other amino acids (C02465 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Nerve Cells
Neuron
Placenta
Platelet
Skeletal Muscle
Testes
Thyroid Gland

Pathways

Name	SMPDB Link	KEGG Link
Tyrosine Metabolism	SMP00006	map00350

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	236-237°C
Boiling Point	Not Available
Solubility	3.96 mg/L (at 37°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	0.82	ALOGPS
logP	2.8	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.3	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.43 m³·mol⁻¹	ChemAxon
Polarizability	43.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a9-5090378000-014ef55558b58a3d38f2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Liothyronine,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0009001000-1d47041336da63b556e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-1009001000-15f70073b9018f013c9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000i-0009000000-71c231d7a3ab505815ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0000009000-f932659d1e6d8a622985	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0000009000-6506a7a71dab928abfb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-0900000000-973fc871534b19242cc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0000009000-2770ece749a9fa1042f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-0000009000-881174c66da97022d645	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-0000019000-6f798ae76702a3053339	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-0000219000-d2ca9f0cc3c1b47176b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-056r-0021915000-6f3810619f383bce651a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0000009000-f932659d1e6d8a622985	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0000009000-6506a7a71dab928abfb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fc0-0700119000-1df6db0e3031eb2739fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-973fc871534b19242cc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-ac3c4a198bb017dc7ccc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0000009000-2770ece749a9fa1042f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pb9-0000009000-4d60e144164273111464	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000149000-87babecf610c68223da5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-0039010000-b57f6dd23e6456cf7c1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0010009000-50e441d89395debe176b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0050139000-a259e39ad1204b60b373	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9262431000-bcc1f7554c4e309cef17	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

95% in 4 hours

Mechanism of Toxicity

The hormones, T₄ and T₃, are tyrosine-based hormones produced by the thyroid gland. Iodine is an important component in their synthesis. The major form of thyroid hormone in the blood is thyroxine (T₄). This is converted to the more active liothyronine form by deiodinases in peripheral tissues. Liothyronine acts on the body to increase the basal metabolic rate, affect protein synthesis and increase the body's sensitivity to catecholamines (such as adrenaline). The thyroid hormones are essential to proper development and differentiation of all cells of the human body. To various extents T₄ and T₃ regulate protein, fat and carbohydrate metabolism. Their most pronounced effect is on how human cells use energetic compounds. The thyroid hormone derivatives bind to the thyroid hormone receptors initially to initiate their downstream effects.

Metabolism

Half Life: 2.5 days

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00279

HMDB ID

HMDB0000265

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-10813

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Triiodothyronine

Chemspider ID

Not Available

ChEBI ID

18258

PubChem Compound ID

5920

Kegg Compound ID

C02465

YMDB ID

Not Available

ECMDB ID

ECMDB24026

References

Synthesis Reference

Martin Beasley, David Hause, Irwin Klein, Charles Pamplin, David Reynolds, Kevin Sills, “Controlled release pharmaceutical compositions of liothyronine and methods of making and using the same.” U.S. Patent US20060246133, issued November 02, 2006.

MSDS

Link

General References

1. Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55.

2. Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69

3. Stalenheim EG: Long-term validity of biological markers of psychopathy and criminal recidivism: follow-up 6-8 years after forensic psychiatric investigation. Psychiatry Res. 2004 Jan 1;121(3):281-91.

4. Schwartz CE, May MM, Carpenter NJ, Rogers RC, Martin J, Bialer MG, Ward J, Sanabria J, Marsa S, Lewis JA, Echeverri R, Lubs HA, Voeller K, Simensen RJ, Stevenson RE: Allan-Herndon-Dudley syndrome and the monocarboxylate transporter 8 (MCT8) gene. Am J Hum Genet. 2005 Jul;77(1):41-53. Epub 2005 May 11.

5. Zimmermann-Belsing T, Dreyer M, Holst JJ, Feldt-Rasmussen U: The relationship between the serum leptin concentrations of thyrotoxic patients during treatment and their total fat mass is different from that of normal subjects. Clin Endocrinol (Oxf). 1998 Nov;49(5):589-95.

6. Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4.

7. Mizuma H, Murakami M, Mori M: Thyroid hormone activation in human vascular smooth muscle cells: expression of type II iodothyronine deiodinase. Circ Res. 2001 Feb 16;88(3):313-8.

8. Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8.

9. Gledhill RF, Dessein PH, Van der Merwe CA: Treatment of Raynaud's phenomenon with triiodothyronine corrects co-existent autonomic dysfunction: preliminary findings. Postgrad Med J. 1992 Apr;68(798):263-7.