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125-84-8

Basic Information
CAS No.: 125-84-8
Name: Aminoglutethimide
Article Data: 9
Molecular Structure:
Molecular Structure of 125-84-8 (Aminoglutethimide)
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: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: UN 3249
PSA: 72.19000
LogP: 2.26320
Synthetic route

dimethyl 2-(1-((4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)amino)hex-5-yn-1-ylidene)malonate

125-84-8

aminoglutethimide

Conditions
ConditionsYield
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
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 1h;95%
With hydrogen; palladium on activated charcoal In ethanol91%
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
ConditionsYield
With dmap; triethylamine; α-bromoacetophenone In acetonitrile for 24h; Ambient temperature;
(+-)-3-ethyl-3-<4-nitro-phenyl>-piperidine-2,6-dione

(+-)-3-ethyl-3-<4-nitro-phenyl>-piperidine-2,6-dione

125-84-8

aminoglutethimide

Conditions
ConditionsYield
With nickel; ethyl acetate Hydrogenation;

2-Ethyl-2-(4-nitro-phenyl)-pentanedioic acid

125-84-8

aminoglutethimide

Conditions
ConditionsYield
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
6973-78-0

2-(4-Nitrophenyl)-buttersaeureethylester

125-84-8

aminoglutethimide

Conditions
ConditionsYield
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
98-95-3

nitrobenzene

ammonium sulfite

ammonium sulfite

125-84-8

aminoglutethimide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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.