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HomeProduct name listPemoline

Pemoline

Synonym(s):2-Amino-5-phenyl4(5H)-oxazolone;Phenylisohydantoin

  • CAS NO.:2152-34-3
  • Empirical Formula: C9H8N2O2
  • Molecular Weight: 176.17
  • MDL number: MFCD00083197
  • EINECS: 218-438-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-23 13:52:06
Pemoline Structural

What is Pemoline?

Absorption

Pemoline is rapidly absorbed from the gastrointestinal tract

Toxicity

Side effects include insomnia, anorexia, stomach ache, skin rashes, increased irritability, mild depression, nausea, dizziness, headache, drowsiness, and hallucinations

Chemical properties

White Solid

Originator

Deltamine,Aron,France,1960

The Uses of Pemoline

A CNS stimulant. Controlled Substance

Indications

For treatment of Attention Deficit Hyperactivity Disorder (ADHD)

Background

In 2005, the Food and Drug Administration (FDA) withdrew approval for pemoline. In March 2005, Abbott Laboratories (Cylert marketer) had discontinued the production of Cylert arguing economic reasons.

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 A central nervous system stimulant, it was used to treat hyperactivity disorders in children, but withdrawn from use following reports of serious hepatotoxicity.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.

Pharmacokinetics

Pemoline belongs to the group of medicines called central nervous system (CNS) stimulants. It is used to treat attention deficit hyperactivity disorder (ADHD). Pemoline stimulates the brain, probably by affecting neurotransmitters, the chemicals in the brain that nerves use to communicate with each other.

Metabolism

Hepatic

Properties of Pemoline

Melting point: 255-256°C
Boiling point: 307.77°C (rough estimate)
Density  1.2662 (rough estimate)
refractive index  1.5570 (estimate)
storage temp.  Store at RT
solubility  DMSO: soluble28mg/mL
form  solid
pka pKa 10.5 (Uncertain)
color  white
CAS DataBase Reference 2152-34-3(CAS DataBase Reference)
NIST Chemistry Reference 4(5H)-oxazolone, 2-amino-5-phenyl-(2152-34-3)

Safety information for Pemoline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

Computed Descriptors for Pemoline

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