Pemoline

Pemoline, sold under the brand name Cylert among others, is a stimulant medication which has been used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy. It has been discontinued in most countries due to rare but serious problems with liver toxicity. The medication was taken by mouth.

Pemoline
Clinical data
Trade namesCylert, others
Other namesPheniminooxazolidinone; Phenylisohydantoin; Phenylpseudohydantoin; Phenilone; 2-Imino-5-phenyl-4-oxazolidinone; 2-Amino-5-phenyl-1,3-oxazol-4(5H)-one
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding≤50%
MetabolismLiver
MetabolitesVarious
Elimination half-life7–12 hours
ExcretionMainly urine
Identifiers
  • (RS)-2-amino-5-phenyl-1,3-oxazol-4(5H)-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.763
Chemical and physical data
FormulaC9H8N2O2
Molar mass176.175 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C2\N=C(/OC2c1ccccc1)N
  • InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12) Y
  • Key:NRNCYVBFPDDJNE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Side effects of pemoline include insomnia, decreased appetite, abdominal pain, irritability, and headaches. Rarely, the medication can cause serious liver damage, and this can result in liver transplantation or death. Pemoline is a psychostimulant and acts as a selective dopamine reuptake inhibitor and releasing agent. Hence, it functions as an indirect agonist of dopamine receptors. Pemoline has little effect on norepinephrine and hence has minimal or no cardiovascular or sympathomimetic effects, in contrast to many other stimulants.

Pemoline was synthesized in 1913 but was not discovered to be a stimulant until the 1930s and was not used in the treatment of ADHD until 1975. It was withdrawn due to liver toxicity in many countries between 1997 and 2005, including the United States. However, it remains available in Japan for the treatment of narcolepsy at lower doses than used for ADHD. Pemoline is a schedule IV controlled substance in the United States due to its relation to other stimulants and a potential for misuse. It seems to have less misuse potential than other stimulants.

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