D-Tetrandrine supplier | CasNO.518-34-3

Name
D-Tetrandrine
EINECS 683-095-7
CAS No. 518-34-3
Article Data21
CAS DataBase
Density 1.172 g/cm³
Solubility
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
Appearance solid
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 61.86000
LogP 7.03820

Synthetic route

: 186581-53-3, 908094-01-9
diazomethane

: 26137-45-1
(+)-penduline

: 518-34-3
Tetrandrin

Conditions

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

: C38H43BrN2O6

: 518-34-3
Tetrandrin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 2-fluoro-3-trifluoromethylbenzyl iodide

: 518-34-3
Tetrandrin

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

Conditions

Conditions	Yield
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

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

: 2-methoxy-5-trifluoromethylbenzyl iodide

: 518-34-3
Tetrandrin

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

Conditions

Conditions	Yield
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

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

: 32247-96-4
3,5-bis(trifluoromethyl)benzyl bromide

: 518-34-3
Tetrandrin

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

Conditions

Conditions	Yield
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

: 110-15-6
succinic acid

: 141776-91-2
1-bromomethyl-3,5-difluoro-benzene

: 518-34-3
Tetrandrin

: C52H52F4N2O6(2+)*2Br(1-)*C4H6O4

Conditions

Conditions	Yield
Stage #1: 1-bromomethyl-3,5-difluoro-benzene; Tetrandrin With 1-butyl-3-methylimidazolium trifluoroacetate In water at 50℃; for 6h; Sonication; Stage #2: succinic acid for 2h; pH=7.5; Reagent/catalyst; Solvent; Temperature; Heating;	95.17%

...Expand

: 2-methoxy-5-trifluoromethylbenzyl chloride

: 518-34-3
Tetrandrin

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

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In water at 160℃; for 0.2h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;	94.4%
With potassium oxide In N,N-dimethyl-formamide at 140℃; for 0.5h;	9.15 g

: 402-49-3
4-bromomethyltrifluoromethylbenzene

: 518-34-3
Tetrandrin

: C54H54F6N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With triethylhexadecylammonium chloride In water at 200℃; for 0.1h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;	94.14%

: 518-34-3
Tetrandrin

: 62067-29-2
5-bromo-tetrandrine

Conditions

Conditions	Yield
With bromine; acetic acid; trifluoroacetic acid In water at -15℃; for 4.5h;	94%
With bromine; acetic acid; trifluoroacetic acid In water at -20 - -15℃; for 4.5h;	93.4%
With bromine; acetic acid; trifluoroacetic acid In water for 0.0833333h; Heating;
With pyridinium hydrobromide perbromide; acetic acid at 20℃;

: 518-34-3
Tetrandrin

: 74-88-4
methyl iodide

: 22445-73-4, 32434-18-7, 107800-34-0
N,N'-Dimethyl-tetrandrinium-diiodid

Conditions

Conditions	Yield
In acetonitrile at 85℃;	94%

: 518-34-3
Tetrandrin

: 14-nitro-tetrandrine

Conditions

Conditions	Yield
With nitric acid In dichloromethane; ethyl acetate at 0 - 20℃; Inert atmosphere;	94%
With nitric acid; acetic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere;	94%
With nitric acid; acetic anhydride In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	93%
With nitric acid; acetic anhydride In chloroform at -10 - 0℃; for 1.5h; Inert atmosphere;	92%

: 98-88-4
benzoyl chloride

: 518-34-3
Tetrandrin

: 7-O-benzoyl-14-nitro-fangchinoline

Conditions

Conditions	Yield
Stage #1: benzoyl chloride; Tetrandrin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 8h; Inert atmosphere; Stage #2: With nitric acid; acetic anhydride In chloroform at -10 - 0℃; for 1.75h; Inert atmosphere;	94%

: 456-41-7
1-(Bromomethyl)-3-fluorobenzene

: 518-34-3
Tetrandrin

: C52H54F2N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In water at 150℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;	93.94%
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃;	89%
With sodium oxide In tetrahydrofuran for 4h; Heating;	7.94g

: 3,4-bis(trifluoromethyl)benzyl bromide

: 518-34-3
Tetrandrin

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

Conditions

Conditions	Yield
With cetyltrimethylammonium chloride In water at 180℃; for 0.1h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;	93.1%

: 64992-03-6
4-(bromomethyl)-2-fluoropyridine

: 104-15-4
toluene-4-sulfonic acid

: 518-34-3
Tetrandrin

: C50H52F2N4O6(2+)*2Br(1-)*C7H8O3S

Conditions

Conditions	Yield
Stage #1: 4-(bromomethyl)-2-fluoropyridine; Tetrandrin In water at 80℃; for 2h; Sonication; Stage #2: toluene-4-sulfonic acid for 1.5h; pH=7.5; Reagent/catalyst; Solvent; Temperature; Heating;	92.74%

...Expand

: 459-46-1
4-Fluorobenzyl bromide

: 518-34-3
Tetrandrin

: C52H54F2N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 4h; Reagent/catalyst; Solvent; Temperature; Sonication;	92.5%

: 110-17-8
(2E)-but-2-enedioic acid

: 85117-99-3
2-(bromomethyl)-1,4-difluorobenzene

: 518-34-3
Tetrandrin

: C52H52F4N2O6(2+)*2Br(1-)*C4H4O4

Conditions

Conditions	Yield
Stage #1: 2-(bromomethyl)-1,4-difluorobenzene; Tetrandrin With tetrabutylammomium bromide In water at 100℃; for 6h; Stage #2: (2E)-but-2-enedioic acid for 8h; pH=7.5; Reagent/catalyst; Solvent; Temperature; Heating;	92.33%

...Expand

: 495-07-8
2,5-difluorobenzyl chloride

: 518-34-3
Tetrandrin

: C52H52F4N2O6(2+)*2Cl(1-)

Conditions

Conditions	Yield
With trimethyloctadecylammonium chloride In water at 120℃; for 6h; Reagent/catalyst; Solvent; Temperature; Microwave irradiation;	92.19%

: 345-35-7
2-fluorobenzyl chloride

: 518-34-3
Tetrandrin

: C52H54F2N2O6(2+)*2Cl(1-)

Conditions

Conditions	Yield
With tetrabutylammomium bromide In water at 60℃; for 12h; Reagent/catalyst; Solvent; Temperature;	90.91%
With potassium hydride In methanol at 65℃; for 8h;	80%

: 518-34-3
Tetrandrin

: C38H42N2O9S

Conditions

Conditions	Yield
With sulfuric acid; sodium sulfate In dichloromethane at 20℃; for 11.25h;	90%

: 75-21-8
oxirane

: 518-34-3
Tetrandrin

: N,N’-dihydroxyethyl-tetrandrine chloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 0 - 20℃;	89%

: 395-44-8
o-trifluoromethylbenzyl bromide

: 518-34-3
Tetrandrin

: C54H54F6N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃;	87.5%

: 766-80-3
1-bromomethyl-3-chlorobenzene

: 518-34-3
Tetrandrin

: C52H54Cl2N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃;	85.3%

: 100-39-0
benzyl bromide

: 518-34-3
Tetrandrin

: (S,S)-N,N'-dibenzyltetrandrine dibromide

Conditions

Conditions	Yield
In acetone for 15h; Heating;	84%

: 620-13-3
1-bromomethyl-3-methyl-benzene

: 518-34-3
Tetrandrin

: C54H60N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃;	82.3%

: 2-(bromomethyl)-1-fluoro-4-(trifluoromethyl)benzene

: 518-34-3
Tetrandrin

: C54H52F8N2O6(2+)*2Br(1-)

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 25 - 90℃;	80.4%

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.

Product Name

D-Tetrandrine

Synthetic route

D-Tetrandrine Specification

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