O-Phenylethylamine

FIGURE 10. Chirality of the coupled electronic transition moments in the preferred conformation of the (S)-Af-salicylidene-o -phenylethylamine [(S)-124]. Reproduced with permission from Reference 110. Copyright (1983) American Chemical Society... 

Figure 15. Schematic representation of the diastereomers generated by desymmetrization of biphenyl-2,2, 6,6 -tetracarboxylic acid with enantiomeric o-phenylethylamines.

The binaphthyl phosphate ester (127) has been proposed as a resolving agent and its absolute configuration determined. A successful resolution procedure for the O-methyl ester of t-butylphosphonothioic acid has been reported. N.m.r. will distinguish between the diastereo-isomers of (128) and between the diastereoisomeric salts of (129) with o -phenylethylamine. ... 

FIGURE 5. Proton NMR spectra of solutions prepared from (S)-o -phenylethylamine [(S)-22] (10 fL) (upper spectrum) and a mixture of (R)- and (S)-Q -phenylethylamine [(/ )- and (S)-22] (7 and 5 pL, respectively) (lower spectrum) in 0.3 iriL of a carbon tetrachloride solution of tris[3-(tert-butylhydroxymethylene)-(7-camphorato]europium(III) (96). The chemical shift scale applies only to the lower spectrum. Reprinted with permission from Reference 82. Copyright (1970) American Chemical Society... 

FIGURE 7. Electronic absorption (EA) and circular dichroism (CD) spectra of (S)-o -phenylethylamine [(S)-22] in methanol. Reproduced from Reference 103 by permission of the Croatian Chemical Society... 

CAS 98-84-0 618-36-0 2627-86-3 (S) 3886-69-9 (R) EINECS/ELINCS 223-423-4 Synonyms 1-(Aminoethyl) benzene 1-Amino-1-phenylethane o-M ethyl benzenemethanam i ne Methyl-o-benzylamine o-Phenethylamine 1-Phenylethanamine 1-Phenylethylamine Phenyl-1 ethylamine o-Phenylethylamine (R)-1-Phenylethylamine... 

Acacia spp. According to White, the tops of A. floribunda Sieb., A. longifolia Willd. and A. pruinosa Cunn. contain tryptamine (3-association with j3-phenylethylamine (N.Z. Journ. Sci. Tech., 1944, 25, B, 157). 

By heating 2-benzyloxycyclohexanone 208 and (R)-l-phenylethylamine in refluxing toluene for 4 days in a Dean-Stark apparatus, the imine 209 was formed, then a rearrangement occurred to give first the a-aminocyclohexanone derivative 210 and finally the Q, o -disubstituted imine 211 with moderate diastereoselectivity. Reduction of this imine with sodium borohydride gave a mixture of two trans diamines (S,S)-212 and (R,R)-212, which were separated by chromatography. The enantiomers of 1-benzyl-1,2-diaminocyclohexanes 213 were then obtained by hydrogenolysis [99] (Scheme 31). 

FIGURE 3 Mean number of injections per day with 14 phenylethylamines for the last 5 days of drug or saline substitution under a 160-response T.O. 3-hour schedule of intravenous injection... 

Thus, when acid 76 was crystallized as a salt with (S)-(-)-l-phenylethylamine ([S]-PEA), the X-ray structure showed that the conformational enantiomer 76a was trapped in the crystal, displaying O - H and O - Ht distances of 2.47 A and 3.41 A, respectively. The conformation of 76a placed the carbonyl oxygen and Hj, closer to the ideal values mentioned in Figure 7.26 as compared to H. A significant preference for Hj, was demonstrated after photolysis at 0 °C and diazomethane workup, when ester 77a (B) was obtained in 65% ee after 90% conversion. Figure 7.27 illustrates the minimal atomic displacements required for reaction by comparing the X-ray structure of the reactant with that of the product, and with a structure obtained at 50% conversion. Better chemical results were obtained by photolysis of 76a with (/ )-CEA, which gave 90% ee of ester of 77a (B) after diazomethane workup. 

The stereochemistries of the reactions between 0-aryl 0-methyl phosphonochloridothioates and nucleophiles have been studied in relation to the synthesis of 1,3,2-oxazaphospholidines. No displacement of chlorine takes place on treatment of O-methyl 0-4-nitrophenyl phosphonochloridothioate with 2-methoxyethanol, and in the presence of 1-phenylethylamine, it is only the latter which reacts. In addition, when the same phosphonochloridothioate is treated with sodium ethoxide, it is the 4-nitrophenoxy group, rather than chlorine, which is displaced. Both displacements were shown to occur with inversion of configuration at phosphorus. The use of such an acid chloride as a two-step 1cyclophosphorylating1 agent of 2-aminoalcohols to give 1,3,2-oxazaphospholidines (209), is illustrated. ... 

In the presence of ZrCU or HC1, cyclization of y - a I k o x y a 11 y I s t a n n a n e 158 bearing (i )-(+)-l-phenylethylamine as a chiral auxiliary occurs to produce trans-fi-aminocyclic ether 159 with high de (91%). As shown in Scheme 3-55, asymmetric addition of an allyl group to the imine carbon can be explained by the modified Cram model 160. The attack of the allylic y-carbon approaches... 

The process of oxidative deamination is the most important mechanism whereby all monoamines are inactivated (i.e. the catecholamines, 5-HT and the numerous trace amines such as phenylethylamine and tryptamine). Monoamine oxidase occurs in virtually all tissues, where it appears to be bound to the outer mitochondrial membrane. Whereas there are several specific and therapeutically useful monoamine oxidase inhibitors, inhibitors of catechol-O-methyltransferase have found little application. This is mainly due to the fact that at most only 10% of the monoamines released from the nerve terminal are catabolized by this enzyme. The main pathways involved in the catabolism of the catecholamines are shown in Figure 2.16. 

In the late 1960s, different types of cyclopropylamines, the A/-substituted cyclopropylamines, were reported [111]. One of the most interesting compounds in the new class was A/-[2-o-chlorophenoxy]-ethyl]-cyclopropylamine (Lilly 51641) (42). This compound noncompetitively inhibited the MAO-catalyzed oxidation of serotonin, tyramine, phenylethylamine, and tryptamine in vitro and increased the serotonin concentration in the whole rat brain in vitro. In structure-activity studies on a series of m- and p-aromatic substituted A/-(phenoxyethyl)cyclopropylamines (43), the degree of inhibition correlated well with a and % values [112]. 

S. Hirota, T. Iwamoto, S. Kishishita, T. Okajima, O. Yamauchi, K. Tanizawa, Spectroscopic observation of intermediates formed during the oxidative half-reaction of copper/topa quinone-containing phenylethylamine oxidase, Biochemistry 40 (2001) 15789-15796. 

Newer MAOI drugs are selective for the MAO-A subtype of the enzyme, and are less likely to interact with foods or other drugs. Monoamine oxidase (MAO) inactivates monoamine substances, many of which are, or are related to, neurotransmitters. The central nervous system mainly contains MAO-A, whose substrates are adrenaline (epinephrine), noradrenaline (norepinephrine), metanephrine, and 5-hydroxyti7ptamine (5-HT), whereas extra-neuronal tissues, such as the liver, lung, and kidney, contain mainly MAO-B which metabolises p-phenylethylamine, phenylethanolamine, o-tyramine, and benzylamine. 

P-Phenylethyl alcohol, 812,816 Phenylethylene, 1015,1024 a-Phenylethylamine, 560, 566 P-Phenylethy,amine, 560, 567,569 Phenylethylbarbituric acid, 1003,1005 P-Phenylethyl bromide, 283 P-Phenylethyl iodide, 288 Phenylglycine-o-carboxylic acid, 980 Phenylglyoxal, 866 Phenylhydrazine, 635, 636 hydrochloride, 636, 637 Phenylhydrazine acetate reagent, 343, 721 ... 

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