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CAS

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77-21-4

DL-Glutethimide, also known as 2-ethyl-2-phenylglutarimide (Doriden), is a nonbarbiturate hypnotic that is structurally similar to barbiturates, particularly phenobarbital. It is used as a racemic mixture with the (+) enantiomer being primarily metabolized on the glutarimide ring and the (-) enantiomer on the phenyl ring. DL-Glutethimide is a white, crystalline powder that is freely soluble in acetone, ethyl acetate, and chloroform; soluble in ethanol and methanol; and practically insoluble in water. It has a half-life of approximately 10 hours and is an enzyme inducer.

77-21-4 Suppliers

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  • 77-21-4 Structure

  • Basic information

    1. Product Name: DL-Glutethimide
    2. Synonyms: 2-Phenyl-2-ethylglutaric acid imide;2-phenyl-2-ethylglutaricacidimide;3-Ethyl-3-phenyl-2,6-diketopiperidine;3-Ethyl-3-phenyl-2,6-dioxopiperidine;3-Phenyl-3-ethyl-2,6-diketopiperidine;3-Phenyl-3-ethyl-2,6-dioxopiperidine;Alfimid;alpha-Ethyl-alpha-phenylglutarimide
    3. CAS NO:77-21-4
    4. Molecular Formula: C13H15NO2
    5. Molecular Weight: 217.26
    6. EINECS: 201-012-0
    7. Product Categories: API
    8. Mol File: 77-21-4.mol

  • Chemical Properties

    1. Melting Point: 84°C
    2. Boiling Point: 357.82°C (rough estimate)
    3. Flash Point: 9℃
    4. Appearance: /
    5. Density: 1.0960 (rough estimate)
    6. Refractive Index: 1.5300 (estimate)
    7. Storage Temp.: ?20°C
    8. Solubility: N/A
    9. PKA: pKa 11.8 (Uncertain)
    10. Water Solubility: 0.95g/L(27 oC)
    11. CAS DataBase Reference: DL-Glutethimide(CAS DataBase Reference)
    12. NIST Chemistry Reference: DL-Glutethimide(77-21-4)
    13. EPA Substance Registry System: DL-Glutethimide(77-21-4)

  • Safety Data

    1. Hazard Codes: Xn,T,F
    2. Statements: 22-39/23/24/25-23/24/25-11
    3. Safety Statements: 36-45-36/37-16-7
    4. RIDADR: 3249
    5. WGK Germany: 1
    6. RTECS: MA4725000
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 77-21-4(Hazardous Substances Data)

77-21-4 Usage

Uses

Used in Pharmaceutical Industry:
DL-Glutethimide is used as a sedative-hypnotic for the treatment of insomnia and other sleep disorders. Due to its low aqueous solubility and high lipophilicity, its dissolution and absorption from the GI tract is somewhat erratic. In therapeutic dosage ranges, adverse effects tend to be infrequent. However, toxic effects in overdose can be as severe as, and possibly more troublesome than, those of the barbiturates.
Brand Names:
C "5", Doridene, Doriden-sed, Doridine, Dorimide, Elrodorm, Gludorm, Sarodormin, Somid, Tardyl.

Originator

Doriden,U.S.V.,US,1955

Manufacturing Process

The 2-phenyl-2-ethyl-pentane-1,5-diacid-mononitrile-(1) of melting point 72° to 76°C, used as starting material in this process, can be produced for example from α-phenyl-butyric acid nitrile by condensation with acrylic acid methyl ester and subsequent hydrolysis of the thus-obtained 2-phenyl-2- ethyl-pentane-1,5-diacid-monomethyl ester-mononitrile-(1) of boiling point 176° to 185°C under 12 mm pressure. 140 parts by weight of 2-phenyl-2-ethyl-pentane-1,5-diacid-mononitrile-(1) are dissolved in 200 parts by volume of glacial acetic acid and, at an initial temperature of 60°C, 100 parts by volume of concentrated sulfuric acid added in portions. In this operation the temperature of the reaction mixture rises to 100°C. The whole is finally maintained for a short time on the boiling water bath, then cooled and poured on ice and neutralized with alkali to a pH of 6. Extraction with chloroform is then effected and the chloroform extract washed with dilute caustic soda solution, dried over calcium chloride, the chloroform evaporated and the residue crystallized from ethyl acetate with addition of ligroin. The obtained 3-phenyl-3-ethyl-2,6-dioxo-piperidine melts at 78° to 81°C.

World Health Organization (WHO)

Glutethimide, a piperidine derivative, was introduced in 1955 for use as a sedative-hypnotic drug. Its addiction liability and severity of withdrawal symptoms are equal to those of the barbiturates and it is controlled under Schedule III of the 1971 Convention on Psychotropic Substances. (Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III), , , 1971)

Hazard

Manufacture and use controlled by law.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: pupillary dilation, ataxia, somnolence, coma, and blood pressure depression. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. Caution: May be habit forming. This is a controlled substance (depressant) listed in the US. Code of Federal Regulations, Title 21 Part 1308.13 (1985)

Purification Methods

Crystallise glutethimide from diethyl ether or ethyl acetate/pet ether. It has m 91-92o (from aqueous EtOH), 87-87.5o (from Et2O/pet ether), 84-87o (from isopropanol), and 83-84o (from Et2O). [Penprase & Biles J Am Pharm Assoc 47 523 1958, Hofmann et al. Helv Chim Acta 40 387, 393 1957, Beilstein 21 III/IV 5493.] The R(+)-enantomer crystallises from EtOAc/pet ether with m 103-104o, and [ ] 20+184o (c 1,

Check Digit Verification of cas no

The CAS Registry Mumber 77-21-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 77-21:
(4*7)+(3*7)+(2*2)+(1*1)=54
54 % 10 = 4
So 77-21-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)

77-21-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-ethyl-3-phenylpiperidine-2,6-dione

1.2 Other means of identification

Product number -
Other names 3-ethyl-3-phenylglutarimide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77-21-4 SDS

77-21-4Relevant articles and documents

Direct Deamination of Primary Amines via Isodiazene Intermediates

Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.

supporting information, p. 17366 - 17373 (2021/11/04)

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

Regiodivergent Copper Catalyzed Borocyanation of 1,3-Dienes

Jia, Tao,He, Qiong,Ruscoe, Rebecca E.,Pulis, Alexander P.,Procter, David J.

, p. 11305 - 11309 (2018/08/28)

Copper catalyzed multi-functionalization of unsaturated carbon-carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4-borocupration and 4,1-borocupration of 1,3-dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2- or 4,3-borocyanation products.

Tert-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts

Qian, Xiaofei,Han, Jianwei,Wang, Limin

, p. 940 - 946 (2016/04/05)

A transition metal-free direct arylation of 2-substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α-tolunitrile derivatives has been synthesized in good to excellent yields of 45-92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.

Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: Multicomponent synthesis of glutarimides

Takaya, Hikaru,Yoshida, Kazunori,Isozaki, Katsuhiro,Terai, Hiroki,Murahashi, Shun-Ichi

, p. 3302 - 3304 (2007/10/03)

Mutual destruction of reagents in acid-and base-promoted reactions in the same container is now avoidable with the iridium polyhydride complex [IrH5(PiPr3)2] (1), which is an ambiphilic Lewis acid and base catalyst. By using catalyst 1, a three-component reaction of nitriles, olefins, and water proceeds efficiently to give glutarimides, which are pharmacologically important (see scheme).

An efficient synthesis of N-benzyl-3-sulfonyl glutarimides. Formal synthesis of the aromatase inhibitor AG-1

Chang, Meng-Yang,Chang, Bo-Rui,Tai, Huo-Mu,Chang, Nein-Chen

, p. 10273 - 10276 (2007/10/03)

A formal [3+3] cycloaddition strategy to substituted glutarimides was studied. N-Benzyl α-sulfonylacetamides and various α,β-unsaturated esters were used as starting materials. (C) 2000 Elsevier Science Ltd.

Aromatase Inhibitors. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 3-Alkylated 3-(4-Aminophenyl)piperidine-2,6-diones

Hartmann, Rolf W.,Batzl, Christine

, p. 1362 - 1369 (2007/10/02)

The synthesis and biological evaluation of 3-alkyl-substituted 3-(4-aminophenyl)piperidine-2,6-diones as inhibitors of estrogen biosynthesis are described .In vitro compounds 4-14 showed a stronger inhibition of human placental aromatase compared to aminoglutethimide (AG, compound 3), which recently has become used for the treatment of hormone-dependent breast cancer.The most active derivative, compound 10, showed a 93-fold stronger inhibition than AG.With the exception of 5, 7, and 8, all other compounds exhibited similar or decreased inhibition of bovine adrenal desmolase compared to AG.Compounds 4 and 6-12 showed a stronger inhibition of the plasma estradiol concentration of pregnant mare serum gonadotropin (PMSG) primed Sprague-Dawley (SD) rats compared to the parent compound.Compounds 4, 6-8, 10, and 12 inhibited the testosterone-stimulated tumor growth of ovariectomized 9,10-dimethyl-1,2-benzanthracene (DMBA) tumor-bearing SD rats more strongly than AG.Being stronger and more selective inhibitors of the estrogen biosynthesis than AG, some of the newly developed derivatives of AG might be better candidates for the treatment of the hormone-dependent human breast cancer.