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

3,3',5-Triiodo-L-thyronine
3,3',5-Triiodo-L-thyronine structure
CAS No.
6893-02-3
Chemical Name:
3,3',5-Triiodo-L-thyronine
Synonyms
L-T3;Thyro3;cytomel;NSC 80203;l-liothyr;tresitope;t3(hormone);triothyrone;Liothyronine;lyothyronine
CBNumber:
CB8221269
Molecular Formula:
C15H12I3NO4
Formula Weight:
650.97
MOL File:
6893-02-3.mol

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

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
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
CAS DataBase Reference
6893-02-3(CAS DataBase Reference)
FDA UNII
06LU7C9H1V
NCI Dictionary of Cancer Terms
Cytomel
NCI Drug Dictionary
Cytomel
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Danger
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
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
8
HS Code  29225090
Toxicity LDLo oral in rat: 7500mg/kg

3,3',5-Triiodo-L-thyronine price More Price(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T-074 3,3′,5-Triiodo-L-thyronine (T3) solution 100?μg/mL in methanol with 0.1N NH3, ampule of 1?mL, certified reference material, Cerilliant? 6893-02-3 1 mL $83 2021-12-16 Buy
Sigma-Aldrich PHR1504 Liothyronine Pharmaceutical Secondary Standard; Certified Reference Material 6893-02-3 500mg $129 2021-12-16 Buy
Sigma-Aldrich 1368008 Liothyronine United States Pharmacopeia (USP) Reference Standard 6893-02-3 250mg $366 2021-12-16 Buy
Sigma-Aldrich T0281 3,3′,5′-Triiodo-L-thyronine thyroid hormone analog 6893-02-3 10 mg $191 2021-12-16 Buy
Sigma-Aldrich T0281 3,3′,5′-Triiodo-L-thyronine thyroid hormone analog 6893-02-3 50 mg $730 2021-12-16 Buy

3,3',5-Triiodo-L-thyronine Chemical Properties,Uses,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

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

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.

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.

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


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

Global( 196)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Suzhou Ryan Pharmachem Technology Co.,Ltd.
0512-68780025-8002
0512-68780025-8004 yybi@ryanchem.com;sales@ryanchem.com CHINA 188 58
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
18007166089 86-18007166089
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Capot Chemical Co.,Ltd.
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Henan DaKen Chemical CO.,LTD.
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Hangzhou FandaChem Co.,Ltd.
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Guangzhou PI PI Biotech Inc
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career henan chemical co
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Hubei Jusheng Technology Co.,Ltd.
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027-59599243 linda@hubeijusheng.com CHINA 28229 58
Xi'an Kono chem co., Ltd.,
13289246953 029-86107037
info@konochemical.com CHINA 3000 58
Standardpharm Co. Ltd.
86-714-3992388
overseasales1@yongstandards.com United States 14344 58

View Lastest Price from 3,3',5-Triiodo-L-thyronine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-01-18 REVERSE T3
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2022-01-06 cytomel raw T3 powder
6893-02-3
US $1.00 / g 100g 99.70% HPLC 5000tons/year Wuhan Dujiang Industrial Co., Ltd.
2021-12-01 L-Triiodothyronine
6893-02-3
US $10.50 / KG 1KG 99 1 ton Hebei Crovell Biotech Co Ltd

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


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