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CAS No.: | 518-34-3 |
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Name: | D-Tetrandrine |
Article Data: | 21 |
Molecular Structure: | |
Formula: | C38H42N2O6 |
Molecular Weight: | 622.761 |
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; |
EINECS: | 683-095-7 |
Density: | 1.172 g/cm3 |
Melting Point: | 219-222 °C |
Boiling Point: | 710.5 °C at 760 mmHg |
Flash Point: | 175.8 °C |
Appearance: | solid |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-36-26 |
PSA: | 61.86000 |
LogP: | 7.03820 |
Conditions | Yield |
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With diethyl ether In methanol for 24h; | 100% |
Tetrandrin
Conditions | Yield |
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With copper(l) iodide; caesium carbonate In toluene for 80h; Reagent/catalyst; Temperature; Ullmann Condensation; Reflux; Inert atmosphere; | 56.5% |
Conditions | Yield |
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With tetraethylammonium bromide In water at 50℃; for 3h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; | 96.64% |
With sodium oxide In glycerol at 300℃; for 0.1h; | 10.5g |
1-(bromomethyl)-2- methoxy-4-(trifluoromethyl)benzene
Tetrandrin
Conditions | Yield |
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With triethyldodecylammonium hydroxide In water at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; | 96.05% |
In dimethyl sulfoxide at -20℃; for 12h; | 7.60g |
Conditions | Yield |
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Stage #1: 2-methoxy-5-trifluoromethylbenzyl chloride; Tetrandrin With 1-hexyl-1-methylpyrrolidin-1-ium bromide In water at 80℃; for 2h; Sonication; Stage #2: citric acid for 2h; pH=7.5; Reagent/catalyst; Solvent; Temperature; Heating; | 96.05% |
Conditions | Yield |
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With tetraethylammonium bromide In water at 50℃; for 4h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; | 95.65% |
With sodium oxide In glycerol at 300℃; for 0.1h; | 10.15g |
Conditions | Yield |
---|---|
With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide In water at 160℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Sonication; | 95.62% |
With potassium hydroxide In methanol at 50℃; for 72h; | 7.60 g |
Conditions | Yield |
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With tetraethylammonium chloride In water at 100℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Sonication; | 95.51% |
With triethylamine In butan-1-ol for 8h; Heating; | 9.1g |
Conditions | Yield |
---|---|
With triethyldodecylammonium hydroxide In water at 60℃; for 6h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; | 95.34% |
With piperidine In 1,4-dioxane at 60℃; for 12h; | 5.95 g |
Conditions | Yield |
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With dodecyltrimethylammonium hydroxide In water at 100℃; for 1h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; | 95.21% |
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃; | 91.5% |
With diethylamine In dichloromethane at 60℃; for 12h; | 10.45 g |
The systematic name of D-Tetrandrine is (1β)-6,6',7,12-tetramethoxy-2,2'-dimethylberbaman. With the CAS registry number 518-34-3, it is also named as Tetrandrine. The product's categories are Alkaloids; Reference Substance, and the other registry numbers are 5990-67-0; 607379-81-7; 6490-80-8; 916770-74-6. Besides, it is solid. In addition, its molecular formula is C38H42N2O6 and molecular weight is 622.75.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.55; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): 2.88; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 63.45; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 439.17; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 61.86 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 178.12 cm3; (15)Molar Volume: 531.1 cm3; (16)Polarizability: 70.61×10-24cm3; (17)Surface Tension: 41.7 dyne/cm; (18)Density: 1.172 g/cm3; (19)Flash Point: 175.8 °C; (20)Melting Point: 219-222 °C; (21)Enthalpy of Vaporization: 103.9 kJ/mol; (22)Boiling Point: 710.5 °C at 760 mmHg; (23)Vapour Pressure: 4.88E-20 mmHg at 25 °C.
Preparation of D-Tetrandrine: this chemical can be prepared by the reaction of Diazomethane with Penduline.
This reaction needs Et2O and Methanol for 24 hours. The yield is 100 %.
Uses of D-Tetrandrine: this chemical is a calcium channel blocker. It is an anti-rheumatic and analgesic drug used for the treatment of rheumatism, hypertension and lung cancer. Additionally, it can be used to produce 6,12,6'-Trimethoxy-2,2'-dimethyl-1βH-berbaman-7-ol.
This reaction needs Iodotrimethylsilane and CHCl3 for 4 hours. The yield is 31.3 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing to avoid contact with skin and eyes. Moreover, please do not breathe dust.
People can use the following data to convert to the molecule structure.
(1)SMILES: O(c7c(OC)cc4c5c7Oc1cc2c(cc1OC)CCN(C)[C@H]2Cc6ccc(Oc3cc(ccc3OC)C[C@@H]5N(C)CC4)cc6)C
(2)InChI: InChI=1/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1
(3)InChIKey: WVTKBKWTSCPRNU-KYJUHHDHBI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | intravenous | 40mg/kg (40mg/kg) | BEHAVIORAL: TREMOR CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 25, Pg. 610, 1994. |
mouse | LD50 | intraperitoneal | 41300ug/kg (41.3mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher,Peop. Rep. China, 1994Vol. -, Pg. 216, 1994. |
mouse | LD50 | intravenous | 37500ug/kg (37.5mg/kg) | Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 25, Pg. 39, 1990. | |
rabbit | LDLo | intravenous | 15mg/kg (15mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 25, Pg. 39, 1990. |