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
• Article Data: 5

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

Chemical Properties

White Solid

Originator

Deltamine,Aron,France,1960

Uses

A CNS stimulant. Controlled Substance

Definition

ChEBI: A member of the class of 1,3-oxazoles that is 1,3-oxazol-4(5H)-one which is substituted by an amino group at position 2 and by a phenyl group at position 5. A central nervous system stimulant, it was used to treat hyperactivity disorders in children, but withdrawn from use following reports of serious hepatotoxicity.

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%. This compound 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.

Brand name

Cylert (Abbott).

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.

General Description

Pemoline, 2-amino-5-phenyl-4(5H)-oxazolone (Cylert), hasa unique structure.The compound is described as having an overall effect onthe CNS like that of methylphenidate. Pemoline requires 3to 4 weeks of administration, however, to take effect. A partialexplanation for the delayed effect may be that one of theactions of the agent, as observed in rats, is to increase therate of synthesis of DA.

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 
• 113-00-8 guanidine nitrate 
• 611-71-2 MANDELIC ACID 
• 50-01-1 guanidine hydrochloride 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 17356-08-0 thiourea 

Downstream Products

• 14021-57-9 5-phenyl-2-piperidin-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 
• 57260-55-6 1-(4-methoxy-cinnamoyl)-2,6-dimethyl-4-(5-phenyl-2-oxo-2-oxazolin-2-yl)-piperazin 
• 76088-38-5 2-(2-Methyl-1-pyrrolidinyl)-5-phenyl-2-oxazolin-4-one 
• 5841-63-4 5-phenyloxazolidine-2,4-dione 
• 5841-66-7 3-Methyl-5-phenyl-oxazol-2,4(3H,5H)-dion 
• 57260-00-1 1-[3t-(3-methoxy-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 57259-96-8 1-[3-(4-methylsulfanyl-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 57260-02-3 1-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-4-[3-(4-trifluoromethyl-phenyl)-acryloyl]-piperazine 
• 57260-35-2 2-{4-[2-hydroxy-2-(3-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-5-phenyl-oxazol-4-one 
• 57260-23-8 1-(6-methoxy-3,4-dihydro-naphthalene-2-carbonyl)-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 57260-24-9 1-[3-(5-nitro-furan-2-yl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 57259-97-9 1-[3-(4-acetylamino-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 

Relevant articles and documents

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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.

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.