Phenethy lamines

Lithium alkylamides (in situ generated from the amine and either n-BuLi or sec-BuLi) generally give higher yields under milder conditions. Thus, n-BuLi (5%) catalyzes the addition of primary and secondary amines to styrene to afford (-phenethy-lamines in moderate to good yields (e.g., Bq. 4.32) [155]. NH, and PhNHj, however, do not add to styrene under these conditions. a-Methylstyrene and 1,1-diphenyleth-ylene can also be hydroaminated. 

Mescaline is chemically classified as a phenethy-lamine. Some of its identified chemical compounds are 3,4,5-trimethoxy-beta-phenethylamine, 3,4,5-trimeth-oxybenzeneethanamine, 3,4,5-trimethoxyphene-thyla-mine, and mescaline. This chemical classification makes the drug different from the other hallucinogens, specifically the more popular LSD, which is classified as an indole. Its chemical formula is CnH17N03. 

A number of difficulties are associated with colour tests on fresh and dried plant material, in addition to those associated with analysing a primary amine such as mescaline. These include the fact that the plant material itself may obscure the colour reaction that takes place. Furthermore, a wide range of primary phenethy-lamines and amphetamines may yield similar colour reactions. The presumptive test which can be satisfactorily used is the Marquis test (see Appendix 1). Positive and negative control tests should also be carried out. An orange-red colour will develop if mescaline is present. However, due to the difficulties associated with interpretation of such results, further confirmation of the presence of mescaline, by using chromatographic and spectroscopic techniques, is required. 

Decomposition of this unstable intermediate produces an amine plus either an aldehyde or a ketone. The term used to describe this process depends on which of the two cleavage products one is interested in. If most of the original molecule remains with the amine (e.g. the N-demethylation of olanzapine shown in Figure 9.21), it s considered oxidative N-dealkylation, but if it ends up in the carbonyl-containing fragment (e.g. conversion of a primary phenethy-lamine to a phenylacetaldehyde and ammonia) it would be instead referred to as oxidative deamination. Notably, FMOs can also carry out N-oxidations of secondary and tertiary amines, for example the pyrrolidine nitrogen of nicotine, but not a-hydroxylations to produce the cleavage products that CYPs can provide. ... 

The method has been used for the synthesis of pyrrolidine constrained phenethy-lamine DPP-IV inhibitor (Scheme 3.18). 

Bogusz, M.J. Kruger, K.-D. Maier, R.-D. Analysis ofunderivatized amphetamines and related phenethy-lamines with high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry, J.Anal.ToxicoL, 2000, 24, 77-84. [SPE LCD 1-5 ng/mL amphetamine fenfluramine methamphetamine phentermine cathinone propylhexedrine ephedrine phenylpropanolamine norfenfluramine phenylethylamine]... 

The iron-catalyzed [4-f2] annulation of ort/zo-nitroanilines with phenethy-lamines was also developed by Nguyen and coworkers (Scheme 9.22), in which... 

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