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54965-24-1

Basic Information
CAS No.: 54965-24-1
Name: Tamoxifen citrate
Article Data: 3
Molecular Structure:
Molecular Structure of 54965-24-1 (Tamoxifen citrate)
Formula: C26H29NO.C6H8O7
Molecular Weight: 563.648
Synonyms: Farmifeno;Oncomox;Tamoxifen citrate (JAN/USP);Tafoxen;Kessar;Tamoxasta;Tamoxifenum [INN-Latin];Nolvadex (TN);Soltamox;Noxitem;Oncotam;Ethanamine, 2-(4-(1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl, (Z)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1);Crisafeno;Nourytan;Tamoplex;Tamofen;ICI 46474;Tamax;Tamoxifene [INN-French];Tamoxen;Nolvadex;Ethanamine,2-[4-[(1Z)-1,2-diphenyl-1- butenyl]phenoxy]-N,N-dimethyl-,2-hydroxy- 1,2,3-propanetricarboxylate (1:1);2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethyl-ethanamine; 2-hydroxypropane-1,2,3-tricarboxylic acid;Valodex;Ethanamine, 2-[4- (1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (Z)-, 2-hydroxy-1,2,3-propane-tricarboxylate (1:1);
EINECS: 259-415-2
Melting Point: 140-144 °C
Boiling Point: 665.9 °C at 760 mmHg
Flash Point: 356.5 °C
Solubility: slightly soluble in water
Appearance: white to off-white powder
Hazard Symbols: ToxicT, IrritantXi
Risk Codes: 45-60-61-22-64-36/37/38
Safety: 53-36/37/39-45-36-26
PSA: 144.60000
LogP: 4.74760
Synthetic route
10540-29-1

tamoxifen

77-92-9

citric acid

54965-24-1

tamoxifen citrate

Conditions
ConditionsYield
In acetonitrile
748-97-0

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol

77-92-9

citric acid

A

54965-24-1

tamoxifen citrate

B

54965-24-1

(Z)-2-(4-(1,2-diphenylbut-1-enyl)phenoxy)-N,N-dimethylethylamine citrate

Conditions
ConditionsYield
Stage #1: 1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol With hydrogenchloride In water; isopropyl alcohol for 5h; Reflux;
Stage #2: citric acid In acetone at -5 - 10℃; for 10h;
A n/a
B 7.5 g
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Consensus Reports

IARC Cancer Review: Human Sufficient Evidence (Benefits outweigh risk for breast cancer patients. 22 Feb, 1997).

Specification

1. Introduction of Tamoxifen citrate

Tamoxifen citrate, with the IUPAC Name of 2-[4-[(Z)-1,2-Diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine ; 2-Hydroxypropane-1,2,3-tricarboxylic acid, is one kind of white to off-white powder. This chemical belongs to the Product Categories which include Active Pharmaceutical Ingredients; Antitumors for Research and Experimental Use; Biochemistry; API's; Intracellular receptor.

Its classification code are Anti-estrogen; Drug / Therapeutic Agent; Human Data; Mutation data; Reproductive Effect and Tumor data. Tamoxifen citrate (CAS NO.54965-24-1) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials, light, heat. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: Nitrogen oxides, carbon monoxide, carbon dioxide. However, its hazardous polymerization will not occur.

2. Properties of Tamoxifen citrate

Tamoxifen citrate has the following properties: (1)Melting point: 140-144 °C; (2)Storage temp.: 2-8 °C; (3)Flash Point: 356.5 °C; (4)Water Solubility slightly soluble; (5)Enthalpy of Vaporization: 102.86 kJ/mol; (6)Boiling Point: 665.9 °C at 760 mmHg; (7)Vapour Pressure: 1.22E-18 mmHg at 25 °C.

3. Structure Descriptors of Tamoxifen citrate

You could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
(2)Isomeric SMILES: CC/C(=C(\C1=CC=CC=C1)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
(3)InChI: InChI=1S/C26H29NO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,4,19-20H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
(4)InChIKey: FQZYTYWMLGAPFJ-OQKDUQJOSA-N

4. Toxicity of Tamoxifen citrate

1.    

add-rat-ipr 60 mg/kg/3D-C

    CNREA8    Cancer Research. 52 (1992),1360.
2.    

add-ham-ipr 10 mg/kg

    CNREA8    Cancer Research. 52 (1992),1360.
3.    

orl-rat TDLo:15,512 mg/kg/1Y-I:CAR

    CRNGDP    Carcinogenesis. 14 (1993),315.
4.    

orl-wmn TDLo:154 mg/kg/1Y-I:EYE

    AJOPAA    American Journal of Ophthalmology. 104 (1987),185.
5.    

orl-rat LD50:1190 mg/kg

    JZKEDZ    Jitchuken, Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Preclinical Reports. 6 (1980),1.
6.    

ipr-rat LD50:575 mg/kg

    JZKEDZ    Jitchuken, Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Preclinical Reports. 6 (1980),1.
7.    

orl-mus LD50:3100 mg/kg

    JRPFA4    Journal of Reproduction and Fertility. 13 (1967),101.
8.    

ipr-mus LD50:218 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),440.

5. Safety Information of Tamoxifen citrate

Confirmed human carcinogen with experimental carcinogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental reproductive effects. Human systemic effects: visual field changes, retinal changes. An anti-estrogenic drug. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT,IrritantXi
Risk Statements: 45-60-61-22-64-36/37/38 
R45:May cause cancer. 
R60:May impair fertility. 
R61:May cause harm to the unborn child. 
R22:Harmful if swallowed. 
R64:May cause harm to breastfed babies. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 53-36/37/39-45-36-26 
S53:Avoid exposure - obtain special instructions before use. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3