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| CAS No.: | 125-84-8 |
|---|---|
| Name: | Aminoglutethimide |
| Molecular Structure: | |
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| Formula: | C13H16N2O2 |
| Molecular Weight: | 232.282 |
| Synonyms: | Glutarimide,2-(p-aminophenyl)-2-ethyl- (6CI,7CI,8CI);(RS)-Aminoglutethimide;3-(4-Aminophenyl)-3-ethylpiperidine-2,6-dione;Ba-16038;Cytadren;DL-Aminoglutethimide;Elipten;NSC 330915;Orimeten;p-Aminoglutethimide; |
| EINECS: | 204-756-4 |
| Density: | 1.173 g/cm3 |
| Melting Point: | 152-154 °C(lit.) |
| Boiling Point: | 457.4 °C at 760 mmHg |
| Flash Point: | 230.4 °C |
| Solubility: | slightly soluble in water |
| Appearance: | white solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| Transport Information: | UN 3249 |
| PSA: | 72.19000 |
| LogP: | 2.26320 |
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- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| With acetic acid at 20℃; for 1h; | 99% |
- 38527-73-0
rac-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 1h; | 95% |
| With hydrogen; palladium on activated charcoal In ethanol | 91% |
| With hydrogen; palladium on activated charcoal In methanol for 5h; Ambient temperature; | 90% |
- 183663-77-6
1-hydroxy-3-ethyl-3-(4-aminophenyl)piperidine-2,6-dione
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| With dmap; triethylamine; α-bromoacetophenone In acetonitrile for 24h; Ambient temperature; |
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| With nickel; ethyl acetate Hydrogenation; |
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 83 percent / trifluoroacetamide, 1-hydroxybenzotriazole, triethylamine, N-(3-dimethylamino)propyl-N-ethylcarbodiimide hydrochloride / 1 h / Ambient temperature 2: 95 percent / H2 / Pd/C / ethanol / 1 h / 760 Torr View Scheme | |
| Multi-step reaction with 3 steps 1: 81 percent / N-ethyl-N-dimethylaminopropylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, triethylamine / CH2Cl2 / 0 °C 2: 10percent Pd/C, H2 / methanol / 2 h 3: triethylamine, bromoacetophenone, DMAP / acetonitrile / 24 h / Ambient temperature View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 2: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 3: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 58 percent / NaH / dimethylformamide / 2 h / 0 °C 2: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 3: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 4: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme | |
| Multi-step reaction with 4 steps 1: 65 percent / NaH / dimethylformamide / 2.5 h / 0 °C 2: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 3: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 4: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme |
- 203808-68-8
4-(ethoxycarbonyl)-4-(4'-nitrophenyl)hexanonitrile
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 2: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme |
- 183663-75-4
1-benzyloxy-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 10percent Pd/C, H2 / methanol / 2 h 2: triethylamine, bromoacetophenone, DMAP / acetonitrile / 24 h / Ambient temperature View Scheme |
- 74220-50-1
2-ethyl-2-phenylglutarodinitrile
- 125-84-8
aminoglutethimide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 59 percent / concd H2SO4, CH3CO2H / 6 h 2: 9 percent / concd H2SO4, 63percent aq. HNO3 / 2 h / -10 - 0 °C 3: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme |
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Specification
The Aminoglutethimide is an organic compound with the formula C13H16N2O2. The IUPAC name of this chemical is 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione. With the CAS registry number 125-84-8, it is also named as 2,6-piperidinedione, 3-(4-aminophenyl)-3-ethyl-. The product's categories are Antitumors for Research and Experimental Use; Biochemistry; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a white solid, which should be stored in a closed palce at temperature of 2 - 8 °C. It is used as an aromatase inhibitor and blocks adrenal steroidogenesis.
Physical properties about Aminoglutethimide are: (1)ACD/LogP: 1.41; (2)ACD/LogD (pH 5.5): 1.38; (3)ACD/LogD (pH 7.4): 1.41; (4)ACD/BCF (pH 5.5): 6.54; (5)ACD/BCF (pH 7.4): 6.98; (6)ACD/KOC (pH 5.5): 130.94; (7)ACD/KOC (pH 7.4): 139.87; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 40.62 Å2; (12)Index of Refraction: 1.566; (13)Molar Refractivity: 64.58 cm3; (14)Molar Volume: 197.9 cm3; (15)Polarizability: 25.6×10-24cm3; (16)Surface Tension: 46.6 dyne/cm; (17)Density: 1.173 g/cm3; (18)Flash Point: 230.4 °C; (19)Enthalpy of Vaporization: 71.75 kJ/mol; (20)Boiling Point: 457.4 °C at 760 mmHg; (21)Vapour Pressure: 1.5E-08 mmHg at 25°C.
Preparation: this chemical can be prepared by 3-ethyl-3-(4-nitro-phenyl)-piperidine-2,6-dione. This reaction will need reagent H2, catalyst 10percent Pd/C and solvent ethanol. The yield is about 91%.
Uses of Aminoglutethimide: it can be used to produce o-iodoaminoglutethimide by heating. It will need reagent I2/KI and solvent methanol, H2O with reaction time of 30 min. The yield is about 70%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NC(=O)CCC1(c2ccc(N)cc2)CC
(2)InChI: InChI=1/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
(3)InChIKey: ROBVIMPUHSLWNV-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
(5)Std. InChIKey: ROBVIMPUHSLWNV-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| man | LDLo | oral | 21mg/kg/3D-I (21mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Annals of Internal Medicine. Vol. 105, Pg. 633, 1986. |
| mouse | LD50 | intraperitoneal | 625mg/kg (625mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC | Journal of Medicinal Chemistry. Vol. 18, Pg. 736, 1975. |
| women | TDLo | oral | 20500mg/kg/94 (20500mg/kg) | BLOOD: AGRANULOCYTOSIS | British Medical Journal. Vol. 291, Pg. 970, 1985. |