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CAS No.: | 10540-29-1 |
---|---|
Name: | Tamoxifen |
Article Data: | 69 |
Molecular Structure: | |
Formula: | C26H29NO |
Molecular Weight: | 371.522 |
Synonyms: | Ethanamine,2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (Z)-;Ethanamine, 2-[4-[(1Z)-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-(9CI);Ethylamine, 2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (Z)-(8CI);(Z)-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine;ICI47699;Mammaton;Novaldex;Z-Tamoxifen;trans-Tamoxifen;? Tamoxifen; |
EINECS: | 234-118-0 |
Density: | 1.042 g/cm3 |
Melting Point: | 97-98 °C(lit.) |
Boiling Point: | 482.3 °C at 760 mmHg |
Flash Point: | 140 °C |
Solubility: | Insoluble in water. Soluble in methanol, ethanol, propanol or propylene glycol.Soluble in dimethyl sulfoxide, dichloromethane and ethanol. Insoluble in water. |
Appearance: | White crystalline solid |
Hazard Symbols: | T, Xi |
Risk Codes: | 45-60-61-64-36/37/38 |
Safety: | 53-45-36-26 |
PSA: | 12.47000 |
LogP: | 5.99610 |
(Z)-1-<4-(2-chloroethoxy)phenyl>-1,2-diphenyl-1-butene
dimethyl amine
tamoxifen
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 65℃; for 12h; Inert atmosphere; | 99% |
In ethanol at 80℃; for 16h; | 93% |
In ethanol at 75℃; for 72h; | 85 mg |
2-(N,N-dimethylamino)ethanol
tamoxifen
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate at 110℃; for 53h; Inert atmosphere; | 96% |
1-phenyl-1-(p-hydroxyphenyl)-2-phenylbut-1-ene
(2-chloroethyl)dimethylamine hydrochloride
tamoxifen
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; toluene at 80 - 85℃; for 3h; Inert atmosphere; | 93% |
With sodium ethanolate In ethanol for 24h; Heating; | 60% |
With sodium hydride 1.) DMF, 2.) 50 deg C; Yield given. Multistep reaction; |
iodobenzene
(E)-N,N-dimethyl-2-(4-(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)phenoxy)ethanamine
tamoxifen
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; potassium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; water at 60℃; for 24h; Suzuki-Miyaura Coupling; regioselective reaction; | 93% |
A
tamoxifen
Conditions | Yield |
---|---|
In ethanol pH=7.2; UV-irradiation; | A 91% B n/a |
(Z)-2-(4-(1,2-diphenylbuta-1,3-dien-1-yl)phenoxy)-N,N-dimethylethanamine
tamoxifen
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate for 2h; atmospheric pressure; | 85% |
With hydrogen; palladium on activated charcoal |
tamoxifen
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In ethyl acetate at 22℃; for 2h; | 85% |
(E)-1,2-diphenyl-1-butene boronic acid
[2-(4-iodophenoxy)ethyl]dimethylamine
A
1,2-diphenyl-butan-1-one
B
tamoxifen
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 18h; Suzuki-Miyaura cross-coupling; Heating; | A n/a B 73% |
(Z)-1-iodo-1,2-diphenyl-1-butene
(4-(2-(dimethylamino)ethoxy)phenyl)boronic acid
tamoxifen
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki-Miyaura cross-coupling; Heating; | 73% |
(E)-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-2-(4-tolyl)thioethene
ethylmagnesium chloride
tamoxifen
Conditions | Yield |
---|---|
With Ni(1,2-bis(diphenylphosphino)ethane)Cl2 In diethyl ether for 15h; Inert atmosphere; Reflux; | 73% |
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 66 ,1996,p. 253.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 66 ,1996,p. 253.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) (Benefits outweigh risk for breast cancer patients. 22 Feb, 1997). EPA Genetic Toxicology Program.
The Novadex is an organic compound with the formula C26H29NO. The IUPAC name of this chemical is 2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine. With the CAS registry number 10540-29-1, it is also named as 1-p-b-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene. The product's categories are Active Pharmaceutical Ingredients; Protein Kinase Inhibitors and Activators; Intermediates & Fine Chemicals; Pharmaceuticals; Isotope Labeled Compounds. Besides, it is a white crystalline solid, which should be stored in a closed cool and dry place at temperature of 2 - 8 °C. It acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism. Also, it is a nonsteroidal estrogen antagonist of interest in the treatment of some forms of breast cancer and it is a Protein Kinase C inhibitor, and induces apoptosis in human malignant glioma cell lines.
Physical properties about Novadex are: (1)ACD/LogP: 7.88; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.04; (4)ACD/LogD (pH 7.4): 6.58; (5)ACD/BCF (pH 5.5): 827.41; (6)ACD/BCF (pH 7.4): 28455.67; (7)ACD/KOC (pH 5.5): 664.18; (8)ACD/KOC (pH 7.4): 22842.23; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 12.47 Å2; (12)Index of Refraction: 1.582; (13)Molar Refractivity: 118.89 cm3; (14)Molar Volume: 356.2 cm3; (15)Polarizability: 47.13×10-24cm3; (16)Surface Tension: 40.4 dyne/cm; (17)Density: 1.042 g/cm3; (18)Flash Point: 140 °C; (19)Enthalpy of Vaporization: 74.72 kJ/mol; (20)Boiling Point: 482.3 °C at 760 mmHg; (21)Vapour Pressure: 1.85E-09 mmHg at 25°C.
Preparation: this chemical can be prepared by (E,Z)-2-(4-bromophenyl)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1-phenyl-1-butene hydrochloride. This reaction will need reagent H2, catalyst 5 percent Pd on C and solvent dimethylformamide. The reaction time is 60 min. The yield is about 92%.
When you are using this chemical, please be cautious about it as the following:
It may cause cancer and may impair fertility. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. It may cause harm to the unborn child and breast-fed babies. When you are using it, wear suitable protective clothing. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccc(cc1)/C(c2ccccc2)=C(\c3ccccc3)CC)CCN(C)C
(2)InChI: InChI=1/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
(3)InChIKey: NKANXQFJJICGDU-QPLCGJKRBF
(4)Std. InChI: InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
(5)Std. InChIKey: NKANXQFJJICGDU-QPLCGJKRSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 575mg/kg (575mg/kg) | Journal of Antibiotics. Vol. 43, Pg. 1533, 1990. | |
mouse | LD50 | oral | 2150mg/kg (2150mg/kg) | Drugs of the Future. Vol. 9, Pg. 186, 1984. | |
rat | LD50 | intraperitoneal | 700mg/kg (700mg/kg) | Drugs of the Future. Vol. 9, Pg. 186, 1984. | |
rat | LD50 | oral | 4100mg/kg (4100mg/kg) | Drugs of the Future. Vol. 9, Pg. 186, 1984. | |
women | TDLo | oral | 5600ug/kg/1W- (5.6mg/kg) | SKIN AND APPENDAGES (SKIN): BREAST: OTHER | British Medical Journal. Vol. 291, Pg. 1172, 1985. |
women | TDLo | unreported | 200ug/kg/D (0.2mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: LEUKOPENIA BLOOD: THROMBOCYTOPENIA | Cancer Treatment Reports. Vol. 60, Pg. 1431, 1976. |
women | TDLo | unreported | 5600ug/kg/2W- (5.6mg/kg) | BLOOD: NORMOCYTIC ANEMIA MUSCULOSKELETAL: JOINTS | British Journal of Rheumatology. Vol. 33, Pg. 583, 1994. |