ChemicalBook > CAS DataBase List > 3,3',5-Triiodo-L-thyronine

3,3',5-Triiodo-L-thyronine

Product Name
3,3',5-Triiodo-L-thyronine
CAS No.
6893-02-3
Chemical Name
3,3',5-Triiodo-L-thyronine
Synonyms
Liothyronine;cytomel;L-T3;O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine;l-triiodothyronine;triiodo-l-thyronine;Thyro3;NSC 80203;l-liothyr;tresitope
CBNumber
CB8221269
Molecular Formula
C15H12I3NO4
Formula Weight
650.97
MOL File
6893-02-3.mol
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3,3',5-Triiodo-L-thyronine Property

Melting point:
234-238 °C(lit.)
alpha 
23 º (c=2 in ethanol)
Boiling point:
232°C (rough estimate)
Density 
2.2155 (estimate)
Flash point:
9°C
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Very Slightly)
pka
pKa 8.5 (Uncertain);8.4 (Uncertain);8.45 (Uncertain)
form 
powder
color 
Off-white to pale yellow
optical activity
[α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2
Water Solubility 
Insoluble in water, ethanol and propylene glycol. Soluble in dilute alkalies.
Sensitive 
Light Sensitive
Merck 
14,5510
BRN 
2710227
Stability:
Light Sensitive
CAS DataBase Reference
6893-02-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi,T,F
Risk Statements 
20/21/22-36/37/38-39/23/24/25-23/24/25-11
Safety Statements 
36-26-36/37/39-45-36/37-16
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
AY6750000
F 
8
HS Code 
29225090
Hazardous Substances Data
6893-02-3(Hazardous Substances Data)
Toxicity
LDLo oral in rat: 7500mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T-074
Product name
3,3′,5-Triiodo-L-thyronine (T3) solution
Purity
100?μg/mL in methanol with 0.1N NH3, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$106
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR1504
Product name
Liothyronine
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500mg
Price
$173
Updated
2024/03/01
Sigma-Aldrich
Product number
1368008
Product name
Liothyronine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
250mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
T0453
Product name
3,3',5-Triiodo-L-thyronine
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$101
Updated
2024/03/01
Alfa Aesar
Product number
H34068
Product name
3,3',5-Triiodo-L-thyronine, 95%
Packaging
1g
Price
$215.65
Updated
2024/03/01
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3,3',5-Triiodo-L-thyronine Chemical Properties,Usage,Production

Description

Crystalline T3 (liothyronine sodium, Cytomel) has a rapid onset and short duration of action. It is the therapy of choice when it is desirable to have rapid onset or cessation of activity, such as in patients with heart disease.

Chemical Properties

Off-White Solid

Originator

Cytomel,SKF,US,1956

Uses

T3 or 3,3',5-Triiodo-L-thyronine is a thyroid hormone involved with many physiological processes in the human body including growth and development, metabolism, body temperature and heart rate. Free and total T3 serum levels are measured by LC-MS/MS for determination of hyperthyroidism caused by excess T3. This Certified Spiking Solution? is suitable for use as a starting material in preparation of linearity standards, calibrators, and controls for thyroid hormone testing methods by LC-MS/MS.

Uses

3,3’,5-Triiodo-L-thyronine (Levothyroxine EP Impurity A) is one of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

Uses

One of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.

Application

3,3′,5′-Triiodo-L-thyronine (T3) is an endocrine hormone produced by the thyroid gland and is regarded as an active thyroid hormone at cellular level. Thyroxine (T4) serves as a precursor for T3 and is generated in extrathyroidal tissues.
3,3′,5-Triiodo-L-thyronine sodium salt has been used for inducing thyroid hormone manipulations in mice. It has also been used In cell culturing of hippocampal, retinal, proximal tubule and glomerular explant.

Definition

ChEBI: An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxi e in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.

Manufacturing Process

The 3,5-diiodo compound used as a starting material is a known material and may be prepared by the method in British Patents 643,089 and 671,070 and in the Journal of the Chemical Society, London, 1949, page 3424.
Synthesis: L-diiodo thyronine (1.05 g) is dissolved in ammonia (specific gravity 0.880) (40 ml) and methanol (40 ml) and iodinated slowly with shaking with N-iodine in KI solution at room temperature. After iodination,most of the ammonia and methanol are removed by evaporation under diminished pressure, water is added to the original volume, the solution is heated to 60°C and brought to pH 4 with hydrochloric acid. A crystalline precipitate is obtained which after cooling to room temperature is collected and washed with water. At this stage, the crude triiodo thyronine is contaminated with thyroxine and a little unchanged diiodo thyronine.
Purification: The crude precipitate is dissolved in boiling 2N HCl (300 ml) and filtered from the relatively insoluble thyroxine hydrochloride. The hot filtrate is brought to pH 4 with 5N NaOH and triiodo thyronine again separates; after chilling at 0° to 4°C it is collected, washed with water and dried. The yield of triiodo thyronine is 70 to 75% of the theoretical. This triiodo thyronine still contains some thyroxine (about 10%).
The final purification consists of chromatographic separation of thyroxine and triiodo thyronine on a kieselguhr column using 20% chloroform in n-butanol equilibrated with 0.5N NaOH as the developing solvent. 80 to 100 mg triiodo thyronine is purified during each run on a 50 g kieselguhr column. Pure Ltriiodo thyronine has MP 236° to 237°C (dec.) and [α]D29.5° = +21.5 in a 4.75% solution in a mixture of 1 part of N HCl and 2 parts of ethanol. Liothyronine is commonly used as the sodium salt.

brand name

Triomet-131 (Abbott); Tri-Thyrotope (Bristol-Myers Squibb).

Therapeutic Function

Thyroid hormone

Biological Activity

3,3′,5′-Triiodo-L-thyronine (T3) increases the rates of protein synthesis, stimulates the breakdown of cholesterol and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression. The interaction of T3 with nonhistone proteins in the chromatin initiates the thyroid hormone activity. Thyroid hormones regulate the differentiation and development of tissues and affect a number of metabolic processes. The level of circulating T3 hormone is reduced in hypothyroidism.

Biochem/physiol Actions

3,3′,5-Triiodo-L-thyronine also referred to as O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine or T3 is the biologically active thyroid hormone. In hypothyroidism pateints, triiodothyronine enhances mood and neuropsychological function. The product also positively regulates the hepatic FGF21 expression and stimulates the metabolic breakdown of glucose, fats, and proteins by enhancing the levels of numerous metabolic enzymes such as hexokinase, liver glucose 6-phosphatase as well as mitochondrial enzymes for oxidative phosphorylation. Additionally, the product facilitates the normal body growth in children and is pivotal for central nervous system maturation in foetus.

storage

-20°C

Purification Methods

Likely impurities are as in thyroxine. Purify it by dissolving in dilute NH3 at ~20o, then crystallise it by addition of dilute acetic acid to pH 6. Alternatively 35g are purified by dissolving it in a mixture of EtOH (250mL) and 2N NaOH (100mL), then hot 2N HCl is added to the boiling solution until the pH is 4-5. After cooling for a few hours, the solid is filtered off and dried in a vacuum [m 233-235o(dec)]. [Chambers et al. J Chem Soc 2433 1949, Beilstein 14 III 1566, 14 IV 2373.]

3,3',5-Triiodo-L-thyronine Preparation Products And Raw materials

Raw materials

Preparation Products

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3,3',5-Triiodo-L-thyronine Suppliers

Canada 2 China 227 Europe 2 Germany 3 India 13 Japan 1 Switzerland 1 United Kingdom 9 United States 23 Global 281
Shifang ShengYuan Technology Co., Ltd.
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0838-6510595 13402890778 18881099744
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Suzhou Pharmaceutical Technology co.,ltd
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0510-88771160 18051901298
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0510-8877116
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Suzhou Ryan Pharmaceutical Technology Co., Ltd.
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0512-68780025 18962125825
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sales@ryanchem.com
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J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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021-61259108 18621169109
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86-21-61259102
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3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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3bsc@sina.com
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Alfa Aesar
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400-6106006
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021-67582001/03/05
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TCI (Shanghai) Development Co., Ltd.
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Sales-CN@TCIchemicals.com
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Beijing HwrkChemical Technology Co., Ltd
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010-89508211 18501085097
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010-89508210
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Energy Chemical
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View Lastest Price from 3,3',5-Triiodo-L-thyronine manufacturers

Shandong Huizhihan Supply Chain Co., Ltd
Product
Liothyronine 6893-02-3
Price
US $0.00-0.00/Bottle
Min. Order
1Bottle
Purity
99%
Supply Ability
2000
Release date
2024-11-06
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Liothyronine 6893-02-3
Price
US $0.00-0.00/g
Min. Order
10g
Purity
95%-101%
Supply Ability
1000g
Release date
2023-03-21
Wuhan Nutra Biotechnology Co.,Ltd
Product
Liothyronine;T3;3,3',5-Triiodo-L-thyronine 6893-02-3
Price
US $10.00-0.00/g
Min. Order
1g
Purity
98%+
Supply Ability
100kgs
Release date
2021-05-27

6893-02-3, 3,3',5-Triiodo-L-thyronineRelated Search:

Liothyronine sodium REVERSE T3 Thyroxine-4-hydroxy-3,5-diiodophenyl Ether DISCONTINUED 3,5-Diiodo-L-thyronine 3,3',5-TRIIODOTHYROPROPIONIC ACID 3,5-DIIODO-4'-(4-HYDROXYPHENOXY)BENZOIC ACID N-ForMyl Thyroxine 3,5,3',5'-Tetraiodo Thyroaldehyde 3-IODO-L-TYROSINE 3,3',5,5'-TETRAIODOTHYRO-ACETIC ACID 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetaMide 3,5,3',5'-Tetraiodo Thyrolactic Acid 3,3',5-TRIIODOTHYROACETIC ACID 3,5-DIIODOTHYROACETIC ACID Levothyroxine EP Impurity B Sodium levothyroxine N-Acetyl L-Thyroxine L-Thyroxine-13C9,15N

  • L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo- (9CI)
  • NSC 80203
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  • 3,3,5-TRIIODO-L -THYRONINE 95-98% FREE ACID CRYSTALLINE
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  • 3,3μ,5 Triiodothyronine (T3)
  • 3,3μ,5-Triiodo-L-thyronine, Liothyronine, T3, O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
  • Liothyronine, T3, O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
  • Alanine, 3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-, L
  • l-liothyr
  • 3,3′,5-Triiodo-L-thyronine,O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine, Liothyronine, T3
  • Liothyronine (250 mg)
  • Liothyronine (250 mg)M0D3380.993mg/mg(dr)
  • 3,5,3′-Triiodo-L-thyronine 3,5,3′-Triiodo-L-thyronine
  • 3,3',5-triiodo-L-thyronine 2
  • (S)-2-Amino-3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)propanoic acid
  • L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo
  • Three triiodothyronine
  • 3,3′,5-Triiodo-L-thyronine, >=99%
  • 3,3',5-Triiodo-<small>L</small>-thyronine
  • 3,3,5-Triiodo-L-thyronine≥ 99% (HPLC: Anhydrous basis)
  • 3,3’,5-triiodothyronine
  • 3,5,3’-triiodothyronine
  • 3’,5-triiodo-l-thyronin
  • 4-(3-iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine
  • 5-diiodophenyl)-3-(4-(4-hydroxy-3-iodophenoxy)-l-alanin
  • cytomel
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  • l-liothyronine
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  • 3,3',5'-TRIIODO-L-THYRONINE
  • L-3,3,5-Triiodothyronine, Free Acid
  • 2-amino-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]-propanoic acid
  • Alanine, 3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-, L- (8CI)
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  • β-(4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl)alanine
  • L-3,3',5'-TRIIODOTHYRONINE
  • LiothyronineSodiumB.P.
  • 5-Triiodothyronine
  • 3,3′,5-Triiodo-L-thyronine (T3) solution
  • Levothyroxine Impurity 1（Levothyroxine EP Impurity A）
  • Triiodo-thyroninum (3,3,5-triiodo-L-thyrnine)
  • T3) (Solution)
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  • 3,3',5-Triiodo-L-thyronine &gt
  • O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine USP/EP/BP
  • order fat burners cytomel raw T3 powder
  • l-liothyronine(T3)
  • Thyro3