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

Description

Pemoline, also known as 2-amino-5-phenyl-4(5H)-oxazolone (Cylert), is a member of the class of 1,3-oxazoles with a unique structure. It is a central nervous system stimulant that was used to treat hyperactivity disorders in children. Pemoline has an overall effect on the CNS similar to that of methylphenidate, but it requires 3 to 4 weeks of administration to take effect. One of the actions of the agent, as observed in rats, is to increase the rate of synthesis of dopamine (DA).

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%. 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.

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 
• 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

• 14021-76-2 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 
• 14021-65-9 2-(4-benzyl-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 
• 76097-77-3 5-Phenyl-2-(thiomorpholino)-2-oxazoline-4-one 
• 133958-34-6 (E)-3,5-Dicyclohexyl-9-hydroxymethyl-9-phenyl-3,4,5,6-tetrahydro-2H-oxazolo[3,2-a][1,3,5,7]tetrazocin-8-one 
• 133958-38-0 5-phenyl-3,5-bis(dipropylaminomethyl)-2-imino-4-oxazolidinone 
• 133958-31-3 3-tert-Butyl-7-(tert-butylamino-methyl)-7-phenyl-3,4-dihydro-2H-oxazolo[3,2-a][1,3,5]triazin-6-one 
• 133958-29-9 3-Butyl-6-oxo-7-phenyl-7-hydroxymethyl-2,3,4,5,6,7-hexahydrooxazolo-<3,2-a>-1,3,5-triazine 
• 133958-30-2 3-(3-Dimethylamino-propyl)-7-hydroxymethyl-7-phenyl-3,4-dihydro-2H-oxazolo[3,2-a][1,3,5]triazin-6-one 
• 520-45-6 Dehydracetic acid 
• 15381-90-5 2-acetamido-5-phenyl-4-oxazolinone 
• 133958-35-7 3,5-dimethyl-8-oxo-9-phenyl-9-hydroxymethyl-2,3,4,5,6,7-hexahydrooxazolo-<3,2-a>-1,3,5,7-tetrazocine 

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.