3469-01-0

Basic information

• Product Name: (+)-Pemoline
• Synonyms: 2-Oxazolin-4-one, 2-amino-5-phenyl-, D-(+)- (8CI);4(5H)-Oxazolone, 2-amino-5-phenyl-, (5R)- (9CI);4(5H)-Oxazolone, 2-amino-5-phenyl-, (R)-
• CAS NO: 3469-01-0
• Molecular Formula: C9H8 N2 O2
• Molecular Weight: 176.17
• Mol File: 3469-01-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 271 °C
• Boiling Point: 313.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• PKA: 0.27±0.40(Predicted)
• CAS DataBase Reference: (+)-Pemoline(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Pemoline(3469-01-0)
• EPA Substance Registry System: (+)-Pemoline(3469-01-0)

Safety Data

• Hazardous Substances Data: 3469-01-0(Hazardous Substances Data)

Usage

Description

(+)-Pemoline, also known as pemoline or Betanamin, is a central nervous system stimulant that has been used to treat attention deficit hyperactivity disorder (ADHD) and narcolepsy. It functions by increasing the release and inhibiting the reuptake of dopamine and norepinephrine in the brain, which results in enhanced alertness and focus.
Used in Pharmaceutical Industry:
(+)-Pemoline is used as a therapeutic agent for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy, due to its ability to increase alertness and focus by modulating neurotransmitter levels in the brain.
However, it is important to note that (+)-Pemoline has been withdrawn from the market in many countries because of its potential risk of liver toxicity, which can lead to liver failure. Additionally, it is classified as a Schedule IV controlled substance in the United States due to its potential for abuse and dependence. Long-term use of (+)-Pemoline has also been associated with an increased risk of liver damage, resulting in its limited use and availability.

Upstream product

• 113-00-8 guanidine nitrate 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 17356-08-0 thiourea 
• 62-53-3 aniline 
• 15381-90-5 2-acetamido-5-phenyl-4-oxazolinone 
• 50-01-1 guanidine hydrochloride 
• 611-71-2 MANDELIC ACID 
• 4358-87-6 (RS)-methyl mandelate 
• 100-52-7 benzaldehyde 
• 20698-91-3 (R)-methyl mandelate 

Downstream Products

• 14021-57-9 5-phenyl-2-piperidin-1-yl-oxazol-4-one 
• 14021-62-6 2-morpholin-4-yl-5-phenyl-oxazol-4-one 
• 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 
• 96977-52-5 2-diisobutylamino-5-phenyl-oxazol-4-one 
• 92648-48-1 2-dipropylamino-5-phenyl-oxazol-4-one 
• 92648-47-0 2-diisopropylamino-5-phenyl-oxazol-4-one 
• 32957-00-9 2-[methyl-(1-methyl-prop-2-ynyl)-amino]-5-phenyl-oxazol-4-one 
• 91392-50-6 2-allylamino-5-phenyl-oxazol-4-one 
• 93879-48-2 2-(methyl-phenethyl-amino)-5-phenyl-oxazol-4-one 
• 95434-93-8 2-dibenzylamino-5-phenyl-oxazol-4-one 
• 90915-34-7 2-imino-3-methyl-5-phenyl-oxazolidin-4-one 
• 57260-55-6 1-(4-methoxy-cinnamoyl)-2,6-dimethyl-4-(5-phenyl-2-oxo-2-oxazolin-2-yl)-piperazin 

Relevant articles and documents

Selective Transformation of Vicinal Glycols to α-Hydroxy Acetates in Water via a Dehydrogenation and Oxidization Relay Process by a Self-Supported Single-Site Iridium Catalyst

α-Hydroxy acids have attracted broad attention because of their prevalence in bioactive molecules and biodegradable polymers, but their conventional syntheses are usually restricted to aromatic substrates, especially, in a stepwise manner. Herein, we disclose the transformation of alkyl and aryl vicinal glycols to α-hydroxy acetates in water under the air atmosphere with our solid self-supported NHC-Ir single-site catalyst. Both aliphatic and aromatic glycols are compatible with a much higher catalytic efficiency in the presence of this solid single-site catalyst than other viable molecular catalysts (93% vs a dehydrogenation facilitated by the catalyst, and then it proceeds through an unexpected oxidization relay step by oxygen in the air, leading to the α-hydroxy acetate formation. Our protocol can potentially contribute to the valorization of readily available and inexpensive diols.

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.