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Designer Barbiturates

If only one was active. Are there any others acting at the same site that locate all of their activity in one isomer or the other?
 
Even if both isomers are active, isolating the more active one will be stronger than the racemic mix, as its unlikely that both isomers are of identical potency even if they are both active.

There are a number of barbiturates which have chiral centres on one of the 5-position substituents, but I don't think I've seen any of them be isolated and tested seperately.

I would imagine with most of them the two stereoisomers would have very similar properties and be hard to seperate from the racemic mix, and by the time asymmetric synthesis really became widely used, barbiturate research was pretty much a dead field. Still be interesting though, especially for mapping the shape of the binding site etc.
 
Confiscation Case Involving a Novel Barbiturate Designer Drug

NCJ Number: NCJ 186836

Title: Confiscation Case Involving a Novel Barbiturate Designer Drug

Journal: Canadian Society of Forensic Science Journal Volume:33 Issue:3 Dated:September 2000 Pages:103 to 110

Author(s): H. Ohta ; Y. Suzuki ; R. Sugita ; S. Suzuki ; K. Ogasawara

Publication Date: 09/2000
Pages: 8
Type: Technical reports
Origin: Canada
Language: English

Annotation: This case history explains the seizure and analysis of an unknown drug from a suspicious person in Japan, the scientific techniques used to analyze the drug, and the conclusion that the substance was an unknown barbiturate designer drug.

Abstract: The strange behavior of a medical student led to his detention and a physical search of his belongings and his home. The search revealed a white crystal powder in both the belongings and the home. The drug appeared to be an analogue of phenobarbital; the drug laws restricted its use. The techniques used to determine the drug’s structure included infrared spectrometry, electron impact and fast-atom bombardment mass spectrometry, and proton and carbon magnetic resonance spectroscopy. Results revealed that the compound’s molecular weight was an estimated 274, which was larger than that of any known barbiturates. Analysis also indicated that the seized drug contained a benzyl group, which has not been detected in any commercially available barbiturates. Therefore, the analysis concluded that the seized compound was an unknown barbiturate designer drug with a structure of 1-benzyl-1-ni-butyl-barbituric acid. The study also concluded that identifying any newly produced designer drug is important to aid law reform and drug law enforcement.

Main Term(s): Drug analysis
Index Term(s): Barbiturates ; Foreign police ; Designer drugs ; Reasonable suspicion ; Japan

To cite this abstract, use the following link:
http://www.ncjrs.gov/App/Publications/abstract.aspx?ID=186836
 
You have to be careful with alkylated naphthalenes, some of them can be quite carcinogenic like pronethalol.
 
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