2152-34-3

Basic information

• Product Name: Pemoline
• Synonyms: BiotaMin-d5;MilgaMMa-d5;VOLITAL;TRADON;2-Amino-5-phenyl-1,3-oxazol-4(5H)-one;2-amino-5-phenyl-2-oxazolin-4-on;2-amino-5-phenyl-4(5h)-oxazolon;2-imino-4-keto-5-phenyltetrahydrooxazole
• CAS NO: 2152-34-3
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• EINECS: 218-438-8
• Product Categories: Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 2152-34-3.mol

Chemical Properties

• Melting Point: 255-256°C
• Boiling Point: 307.77°C (rough estimate)
• Flash Point: 143.437 °C
• Appearance: white/solid
• Density: 1.2662 (rough estimate)
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble28mg/mL
• PKA: pKa 10.5 (Uncertain)
• CAS DataBase Reference: Pemoline(CAS DataBase Reference)
• NIST Chemistry Reference: Pemoline(2152-34-3)
• EPA Substance Registry System: Pemoline(2152-34-3)

Safety Data

• Hazard Codes: Xn,C,F,T
• Statements: 22-34-11-20/21/22
• Safety Statements: 16-26-36/37/39-45-36/37-36
• WGK Germany: 3
• RTECS: PB8750000
• Hazardous Substances Data: 2152-34-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pemoline is used as a CNS stimulant for the treatment of hyperactivity disorders in children. It was a controlled substance that helped manage symptoms by increasing the rate of synthesis of dopamine in the brain.
However,

Originator

Deltamine,Aron,France,1960

Manufacturing Process

It is preferably prepared by reacting mandelic acid ethyl ester with guanidine in boiling alcoholic solution whereby it is obtained as difficultly soluble precipitate with a yield of 90%. Pemoline is a white, crystalline compound melting at 256°-257°C with decomposition. It is readily soluble in concentrated aqueous alkali hydroxide solutions and in concentrated aqueous mineral acids.

Therapeutic Function

Psychostimulant

World Health Organization (WHO)

Pemoline was introduced in 1975 for the treatment of attentiondeficit disorder. Because of its central stimulating effects it has also been used in weight control in combination with anorectic agents, laxatives.

Biological Activity

Long-acting central stimulant that induces self-injurious behavior in rats. Acts as an indirect monoamine agonist.

InChI:InChI=1/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

Upstream product

• 62-53-3 aniline 
• 15381-90-5 2-acetamido-5-phenyl-4-oxazolinone 
• 50-01-1 guanidine hydrochloride 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 113-00-8 guanidine nitrate 
• 611-71-2 MANDELIC ACID 
• 17356-08-0 thiourea 

Downstream Products

• 14021-57-9 5-phenyl-2-piperidin-1-yl-oxazol-4-one 
• 14021-62-6 2-morpholin-4-yl-5-phenyl-oxazol-4-one 
• 14021-76-2 5-phenyl-2-piperazin-1-yl-oxazol-4-one 
• 57260-54-5 1-[3-(4-methoxy-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-[1,4]diazepane 
• 14021-58-0 2-(4-methyl-piperazin-1-yl)-5-phenyl-oxazol-4-one 
• 14021-59-1 5-phenyl-2-(4-phenyl-piperazin-1-yl)-oxazol-4-one 
• 57260-42-1 5-phenyl-2-(4-pyridin-2-yl-piperazin-1-yl)-oxazol-4-one 
• 14021-65-9 2-(4-benzyl-piperazin-1-yl)-5-phenyl-oxazol-4-one 
• 96977-52-5 2-diisobutylamino-5-phenyl-oxazol-4-one 
• 14021-68-2 2-[4-(4-methoxy-phenyl)-piperazin-1-yl]-5-phenyl-oxazol-4-one 
• 40504-78-7 2-but-3-ynylamino-5-phenyl-oxazol-4-one 
• 92648-48-1 2-dipropylamino-5-phenyl-oxazol-4-one 
• 57260-37-4 2-[4-(3,4-dichloro-phenyl)-piperazin-1-yl]-5-phenyl-oxazol-4-one 
• 655-05-0 2-(dimethylamino)-5-phenyloxazol-4(5H)-one 

Relevant articles and documents

Structure elucidation of 2-amino-5-phenyl-2-oxazolin-4-one (pemoline) and X-ray structure of its hydrolysis product 5-phenyl-oxazolidine-2,4-dione

In this study we compare spectroscopic properties of pemoline (2-amino-5-phenyl-2-oxazolin-4-one) and its acid hydrolysis product 5-phenyl-oxazolidine-2,4-dione. Crystallization of pemoline from aqueous acetic acid gave single crystals of compound 2, the structure of which was determined by X-ray studies. All four crystallographically independent molecules form dimers linked by N-H?O=C hydrogen bonds.

Callyspongisines A-D: Bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp.

An extract of the Great Australian Bight marine sponge Callyspongia sp. (CMB-01152) displayed inhibitory activity against the neurodegenerative disease kinase targets casein kinase 1 (CK1), cyclin-dependent kinase 5 (CDK5) and glycogen synthase kinase 3 (GSK3β). Chemical investigation, employing HPLC-DAD-MS single ion extraction protocols, facilitated identification of the new bromopyrrole alkaloids, callyspongisines A-D (1-4), and two known co-metabolites, hymenialdisine (5) and 2-bromoaldisine (6). Structure elucidation of 1-6 was supported by detailed spectroscopic analysis and chemical interconversion, as well as biosynthetic and synthetic considerations. Callyspongisine A (1) is only the second reported example of a natural imino-oxazoline, and the first to feature a spiro heterocyclic framework, while callyspongisines B-D (2-4) were speculated to be storage and handling artefacts of 1. The kinase inhibitory activity detected in Callyspongia sp. (CMB-01152) was attributed to 5. This journal is The Royal Society of Chemistry 2014.

Selective Transformation of Vicinal Glycols to α-Hydroxy Acetates in Water via a Dehydrogenation and Oxidization Relay Process by a Self-Supported Single-Site Iridium Catalyst

α-Hydroxy acids have attracted broad attention because of their prevalence in bioactive molecules and biodegradable polymers, but their conventional syntheses are usually restricted to aromatic substrates, especially, in a stepwise manner. Herein, we disclose the transformation of alkyl and aryl vicinal glycols to α-hydroxy acetates in water under the air atmosphere with our solid self-supported NHC-Ir single-site catalyst. Both aliphatic and aromatic glycols are compatible with a much higher catalytic efficiency in the presence of this solid single-site catalyst than other viable molecular catalysts (93% vs a dehydrogenation facilitated by the catalyst, and then it proceeds through an unexpected oxidization relay step by oxygen in the air, leading to the α-hydroxy acetate formation. Our protocol can potentially contribute to the valorization of readily available and inexpensive diols.

Process for the preparation of 2-imino-5-phenyl-4 oxazolidinone and its intermediates

The present invention relates to the production of pemoline and its intermediates.

ACYLATION OF 2-AMINO-5-PHENYL-4-OXAZOLINONE AND 2-AMINO-4-IMIDAZOLINONES

The acylation of 2-amino-5-phenyl-4-oxazolinone and 2-amino-1-methyl-4-imidazolinone with acetyl chloride in benzene in the presence of triethylamine leads to the formation of 2-acetamido-5-phenyl-4-oxazolinone and 2-acetamido-1-methyl-4-imidazolinone.The acylation of 2-amino-4-imidazolinone under the indicated conditions, as well as acetic anhydride, gives 1-acetylimidazolidine-2,4-dione. 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione (dehydroacetic acid) is formed as a side product in the acylation of 2-amino-4-azolinones with acetyl chloride in benzene in the presence of triethylamine.The IR and PMR spectra of the compounds obtained are presented.