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55511-44-9

55511-44-9 Structure

55511-44-9 Structure
IdentificationBack Directory
[Name]

(R)-(+)-AMINOGLUTETHIMIDE 97
[CAS]

55511-44-9
[Synonyms]

CGS-2396
Aminoglutethimide, D-
(R)-(+)-Aminoglutethimide 97%
(R)-(+)-AMINOGLUTETHIMIDE 97
(R)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
(R)-3-(4-aMinophenyl)-3-ethylpiperidine-2,6-dione
(3R)-3-(4-aminophenyl)-3-ethyl-piperidine-2,6-dione
2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-, (3R)-
[Molecular Formula]

C13H16N2O2
[MDL Number]

MFCD03094025
[MOL File]

55511-44-9.mol
[Molecular Weight]

232.28
Chemical PropertiesBack Directory
[Melting point ]

115.5-119.5 °C (lit.)
[Boiling point ]

457.4±45.0 °C(Predicted)
[density ]

1.173±0.06 g/cm3(Predicted)
[storage temp. ]

Storage temp. 2-8°C
[form ]

Solid
[pka]

11.60±0.40(Predicted)
[color ]

Off-white to light yellow
[Optical Rotation]

[α]20/D +160°, c = 1 in methanol
[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)/t13-/m1/s1
[InChIKey]

ROBVIMPUHSLWNV-CYBMUJFWSA-N
[SMILES]

CC[C@@]1(CCC(=O)NC1=O)c2ccc(N)cc2
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Uses]

(R)-(+)-Aminoglutethimide can be used:
  • As a building block for the development of cephalosporin based prodrug for antibody-directed enzyme prodrug therapy (ADEPT).
  • To prepare (R)-3-ethyl-3-(4-(3,4,5-trimethoxybenzylamino)phenyl)piperidine-2,6-dione by reacting with 3,4,5-trimethoxybenzylamine via deaminative coupling reaction.
  • To synthesize (R)-2-fluoro-2-(4-methoxyphenyl)-N-(R)-(+)-aminoglutethimide by enantioselective α-fluorination.

[Definition]

ChEBI: The (3R)-enantiomer of aminoglutethimide.
[in vivo]

(R)-(+)-Aminoglutethimide (5, 50 mg/kg; p.o.) eliminates within 48 hr into urine and feces, mostly in the form of metabolites[2].
(R)-(+)-Aminoglutethimide (1, 10, 50 mg/kg; i.p.; 60 min before training) dose not induce any significant effect in 1 and 10 mg/kg, induces a loss of retention at 50 mg/kg in day-old chicks[3].

[IC 50]

Aromatase
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