D-Tetrandrine

Base Information

• Chemical Name: D-Tetrandrine
• CAS No.: 518-34-3
• Deprecated CAS: 916770-74-6,6490-80-8,607379-81-7,5990-67-0,5990-67-0,607379-81-7
• Molecular Formula: C38H42N2O6
• Molecular Weight: 622.761
• Hs Code.: 29349990
• European Community (EC) Number: 683-095-7
• NSC Number: 91771,77037
• UNII: 29EX23D5AJ,VS4W77H3SD
• DSSTox Substance ID: DTXSID10178062,DTXSID70881383
• Nikkaji Number: J130.138A
• Wikipedia: Tetrandrine
• Wikidata: Q7706612
• NCI Thesaurus Code: C28952
• Metabolomics Workbench ID: 124309
• ChEMBL ID: CHEMBL176045
• Mol file: 518-34-3.mol

Synonyms:Berbaman,6,6',7,12-tetramethoxy-2,2'-dimethyl-, (1b)-;Tetrandrine (6CI,7CI,8CI);(+)-Tetrandrine;(S,S)-Tetrandrine;16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline,3,4,4a,5,16a,17,18,19-octahydro-12,21,22,26-tetramethoxy-4,17-dimethyl-,[4aS-(4aR*,16aR*)]-;Fanchinine;Hanfangchin A;NSC 77037;S,S-(+)-Tetrandrine;Sinomenine A;TTD;Tetrandrin;Tetrandrine;

Chemical Property of D-Tetrandrine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 4.88E-20mmHg at 25°C
• Melting Point: 219-222 °C
• Refractive Index: 1.585
• Boiling Point: 710.5 °C at 760 mmHg
• PKA: 7.70±0.20(Predicted)
• Flash Point: 175.8 °C
• PSA: 61.86000
• Density: 1.172 g/cm³
• LogP: 7.03820
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 622.30428706
• Heavy Atom Count: 46
• Complexity: 979

Purity/Quality:

98% up ^*data from raw suppliers

Tetrandrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC
• Recent ClinicalTrials: Tetrandrine Tablets Used in Hospitalized Adults With COVID-19
• Description: Recently it has been discovered that pronounced drug-dependence and related toxic effects occur in both dogs and rhesus monkeys with this alkaloid on intravenous injection with a dose of 10-150 mg/kg. When rapidly injected, the acute hypotensive effect is very marked and fatal at once. Following drug administration at toxic levels it is found that severe local tissue reaction heptaotoxicity and lymphoid necrosis occurs. At the highest dosage level there is a very definite nephrotoxicity in monkeys and some indications of this in dogs. The evidence available suggests that monkeys are less sensitive to hepatotoxicity with this drug than dogs. Tetrandrine is a bis-benzylisoquinoline alkaloid that has been found in R. stephania roots and has diverse biological activities. It induces autophagy in HeLa, MCF-7, and human foreskin fibroblast (HFF) cells when used at a concentration of 5 μM, an effect that can be reversed by the autophagy inhibitor 3-methyladenine . Tetrandrine inhibits PAF-, thrombin-, collagen-, ADP-, or epinephrine-induced aggregation of isolated human platelets. Priming of mesenchymal stem cells (MSCs) with tetrandrine (5 and 10 μM) reduces TNF-α secretion by RAW 264.7 cells in co-culture. Ear skin transplantation of tetrandrine-primed MSCs decreases ear levels of TNF-α in a mouse model of ear skin inflammation. Tetrandrine (1 mg/kg) increases soleus muscle levels of glucose transporter 4 (Glut4) and decreases plasma glucose levels in a rat model of diabetes induced by streptozotocin .
• Physical properties: Appearance: Needle-like crystals (ether). Solubility: Hardly soluble in water and petroleum ether; soluble in ether and some organic solvents. Melting point: 219– 222?°C. Specific optical rotation: 285° (c?=?1, CHCl3); sensitive to light.
• Uses: Tetrandrine is a lipopolysaccharide-induced microglial suppressor, effectively reducing the production of bacterial inflammatory mediators. Anti-inflammatory, anti-nociceptive. Tetrandrine is used in China to treat high blood pressure. This drug blocked the TPC2 calcium channel required for the Ebola infection process (Robert A. Davey et al., Science 2015, DOI: 10.1126/science.1258758). analgesic, antineoplastic, antihypertensive, lymphotoxin
• Indications: This product is included in national standards for chemical drugs (Volume 14), British Pharmacopoeia (2017), and European Pharmacopoeia (9.0th ed.). Tetrandrine is used for the treatment of mild to moderate hypertension and hypertensive crisis, rheumatism, silicosis, etc.
• Clinical Use: Tetrandrine is used for the treatment of hypertension, angina, termination of paroxysmal supraventricular tachycardia, pulmonary fibrosis, and other diseases in clinical application, and it also has strong antitumor effects. Tetrandrine was also approved for lowering blood glucose and free radical damage; its treatment effect on silicosis is significant and superior to conventional immunosuppressive and cytotoxic drugs.

Technology Process of D-Tetrandrine

There total 40 articles about D-Tetrandrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (+)-penduline (26137-45-1) → Tetrandrin (518-34-3,5990-67-0)

Guidance literature:

With diethyl ether; In methanol; for 24h;

DOI:10.3987/COM-95-7155

Reference yield: 56.5%

C38H43BrN2O6 → Tetrandrin (518-34-3,5990-67-0)

Guidance literature:

With copper(l) iodide; caesium carbonate; In toluene; for 80h; Reagent/catalyst; Temperature; Reflux; Inert atmosphere;

Reference yield: 45.2%

C38H43BrN2O6 → tetrandrine (477-57-6,518-34-3,1263-79-2,23495-89-8,23495-90-1,26137-48-4,26695-12-5,5990-67-0)

Guidance literature:

With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; for 60h; Reagent/catalyst; Solvent; Reflux; Inert atmosphere;

upstream raw materials:

diazomethane

(+)-penduline

methanol

formaldehyd

Downstream raw materials:

tetrandrine

(S)-N-methylcoclaurine

(R)-(-)-O-methylarmepavine

(R)-7-methoxy-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol

Refernces

• 1、 -. "Full-synthetic method of racemic tetrandrine". . . Retrieved 2019/07/10.
• 2、 Kashiwaba, Noriaki,Morooka, Shigeo,Kimura, Michiko,Ono, Minoru,Murakoshi, Yoshie,et al.. "A CHEMISTRY OF BISBENZYLISOQUINOLINE ALKALOID: ISOMERIZATION OF BERBAMINE TO PENDULINE IN METHANOL BY RADICAL REACTION". . p. 2043 - 2048. Retrieved 2007/10/03.