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D-Tetrandrine
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Name

D-Tetrandrine

 EINECS 683-095-7
CAS No. 518-34-3 Density 1.172 g/cm3
PSA 61.86000 LogP 7.03820
Solubility N/A Melting Point 219-222 °C
Formula C38H42N2O6 Boiling Point 710.5 °C at 760 mmHg
Molecular Weight 622.761 Flash Point 175.8 °C
Transport Information N/A Appearance solid
Safety 22-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 518-34-3 (D-Tetrandrine) Hazard Symbols IrritantXi
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;

Article Data 21

D-Tetrandrine Synthetic route

186581-53-3, 908094-01-9

diazomethane

26137-45-1

(+)-penduline

518-34-3

Tetrandrin

Conditions
ConditionsYield
With diethyl ether In methanol for 24h;100%

C38H43BrN2O6

518-34-3

Tetrandrin

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In toluene for 80h; Reagent/catalyst; Temperature; Ullmann Condensation; Reflux; Inert atmosphere;56.5%

4-iodo-3-trifluoromethylbenzyl iodide

518-34-3

Tetrandrin

C54H52F6I2N2O6(2+)*2I(1-)

Conditions
ConditionsYield
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
886500-59-0

1-(bromomethyl)-2- methoxy-4-(trifluoromethyl)benzene

518-34-3

Tetrandrin

C56H58F6N2O8(2+)*2Br(1-)

Conditions
ConditionsYield
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

2-methoxy-5-trifluoromethylbenzyl chloride

77-92-9

citric acid

518-34-3

Tetrandrin

C56H58F6N2O8(2+)*2Cl(1-)*C6H8O7

Conditions
ConditionsYield
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%

2-fluoro-3-trifluoromethylbenzyl iodide

518-34-3

Tetrandrin

C54H52F8N2O6(2+)*2I(1-)

Conditions
ConditionsYield
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

2-methoxy-4-trifluoromethylbenzyl iodide

518-34-3

Tetrandrin

C56H58F6N2O8(2+)*2I(1-)

Conditions
ConditionsYield
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

2-methoxy-5-trifluoromethylbenzyl iodide

518-34-3

Tetrandrin

C56H58F6N2O8(2+)*2I(1-)

Conditions
ConditionsYield
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

3,5-difluorobenzyl iodide

518-34-3

Tetrandrin

C52H52F4N2O6(2+)*2I(1-)

Conditions
ConditionsYield
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
32247-96-4

3,5-bis(trifluoromethyl)benzyl bromide

518-34-3

Tetrandrin

C56H52F12N2O6(2+)*2Br(1-)

Conditions
ConditionsYield
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

D-Tetrandrine Specification

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.

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