Merck
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A9657

Sigma-Aldrich

DL-Aminoglutethimide

Synonym(s):
3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione, 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
Empirical Formula (Hill Notation):
C13H16N2O2
CAS Number:
Molecular Weight:
232.28
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

≥98% (TLC)

form

powder or crystals

color

white

mp

152-154 °C (lit.)

solubility

H2O: slightly soluble 0.2 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.2 mg/mL
0.1 M HCl: soluble
acetonitrile: soluble
methanol: soluble

originator

Novartis

storage temp.

room temp

SMILES string

CCC1(CCC(=O)NC1=O)c2ccc(N)cc2

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)

InChI key

ROBVIMPUHSLWNV-UHFFFAOYSA-N

Gene Information

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Application

DL-Aminoglutethimide has been used:
  • as a steroid synthesis inhibitor to study its effects on steroid synthesis in amphibian Xenopus laevis oocytes
  • as an adrenostatic compound to study its effects on full form Enhanced green fluorescent protein (EGFP) andproopiomelanocortin (POMC) expression in the anterior domain of zebrafish pituitary corticotrophs
  • as an inhibitor of steroidogenic enzymes to study its effects on estrogen receptor (ER) mRNA levels in mouse tumor leydig cell line

Biochem/physiol Actions

DL-Aminoglutethimide is a derivative of the sedative glutethimide. Originally introduced as an anticonvulsant, it was found to cause adrenal insufficiency. Blocks adrenal steroidogenesis by inhibiting the enzymatic conversion of cholesterol to pregnenolone. It also blocks the peripheral conversion (aromatization) of androgenic precursors to estrogens. The D-isomer is 30 times more potent at inhibiting aromatase activity, whereas the L-isomer is more potent at inhibiting cholesterol side-chain cleavage (steroidogenesis).

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A9657.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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