ContaminantDB: Pemoline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:44:47 UTC

Update Date

2016-11-09 01:15:28 UTC

Accession Number

CHEM016825

Identification

Common Name

Pemoline

Class

Small Molecule

Description

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 A central nervous system stimulant, it was used to treat hyperactivity disorders in children, but withdrawn from use following reports of serious hepatotoxicity.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-5-phenyl-4(5H)-oxazolone	ChEBI
2-Imino-4-keto-5-phenyltetrahydrooxazole	ChEBI
2-Imino-5-phenyl-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxooxazolidine	ChEBI
5-Phenylisohydantion	ChEBI
Azoxodon	ChEBI
Betanamin	ChEBI
Cylert	ChEBI
Dantromin	ChEBI
Deltamine	ChEBI
Hyton	ChEBI
Myamin	ChEBI
Nitan	ChEBI
Notair	ChEBI
Pemolina	ChEBI
Pemolinum	ChEBI
Pheniminooxazolidinone	ChEBI
Phenylisohydantoin	ChEBI
Phenylpseudohydantoin	ChEBI
Abbott brand OF pemoline	MeSH
Lilly brand OF pemoline	MeSH
Compounds, pemoline	MeSH
Pemoline compounds	MeSH
Tradon	MeSH
Magnesium, pemoline	MeSH
Mallinckrodt brand OF pemoline	MeSH
PemADD	MeSH
Pemoline magnesium	MeSH
Phenoxazole	MeSH

Chemical Formula

C₉H₈N₂O₂

Average Molecular Mass

176.172 g/mol

Monoisotopic Mass

176.059 g/mol

CAS Registry Number

2152-34-3

IUPAC Name

2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one

Traditional Name

pemoline

SMILES

NC1=NC(=O)C(O1)C1=CC=CC=C1

InChI Identifier

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)

InChI Key

NRNCYVBFPDDJNE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Oxazoline
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-oxazoles (CHEBI:7953 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	0.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.7 m³·mol⁻¹	ChemAxon
Polarizability	17.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-7900000000-ff16f04882fa6bc388b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-1900000000-6304707e673e5496a706	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-1900000000-6304707e673e5496a706	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-6312df1dd9b3c1da44a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-3900000000-355d61158f2b03978708	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-5fdd1bf70ae74ce0100a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05r3-1900000000-9afcde2920ef21e932f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9700000000-37842f170bf0d611bc61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-a834fbdc5b9e8c4b0eb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9700000000-770e8d3a8e42b5bad6c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-6ded2f5c4a0ee37a0e13	Spectrum