Hydroxy tyramine

Dopamine (= 4-(2-Aminoethyl)-benzene-l, 2-diol 3-Hydroxy-tyramine) (catecholamine phenolic)... 

Hydroxy tyramine (VIII) is a catechol derivative and a product of both animal and plant origin. It can be isolated from the mammalian heart (41) and human urine (42). It occurs as an intermediate of the coloring matter in the broom Cytisus scuparius Link (43). Conceivably hydroxy-tyramine is derived from 3,4-dihydroxy phenylalanine by decarboxylation. The specific enzyme, dihydroxyphen3dalanine decarboxylase, for catalysis is present in mammalian kidneys (44, 45) and in the rat liver (46). 

The base can be obtained by heating 3 4-dihydroxyphenylalanine above its melting point. A synthesis starting from tyramine was described by Waser and Sommer (89) it was first nitrated to 3-nitro-tyramine, reduced, and the diazo compound decomposed to 3-hydroxy-tyramine. 

Schmalfuss, H., and A. Heider. 1931. Tyramine and hydroxy-tyramine, the blood-pressure-raising substances of the pod of the common broom Sarothamnus scoparius Wimm. Biochem. Z. 236 226-230. 

The sympathomimetic action of natural and synthetic hydroxy-tyramine has been studied by llaymond-Hamet (129),... 

Werle and Raub (91) observed that the seedlings of Cytisus scoparius are able to decarboxylate 3 4-dihydroxyphenylalanine to 3-hydroxy-tyramine, and Vinet (92) showed that kidney tissue, in vitro, can effect the same decarboxylation. Adrenal medulla converts the latter to adrenaline by methylation and oxidation, but cannot form adrenaline from dihydroxyphenylalanine or tyramine. 

The pharmacological properties of the catecholamines (3-hydroxytyr-amine, /-noradrenaline, adrenaline) are of a sympathomimetic nature. 3-Hydroxy tyramine increases the blood pressure in animals and in man. 60, 63. 212, 299, 823, 998,1020, 1022,1033-43) rcspective potcncy of adrenaline, hydroxytyramine, and tyramine on the blood... 

Hydroxy tyramine t-Noradrenaline Tryptamine 5-Hydroxytryptamine Bufotenine E thylamine Ally I amine Isoamylamine Butylamine Jsobutylamine Cadaverine Jsopropylamine... 

It may be concluded, on the one hand, from the examples already given in which there is a decreased excretion and abnormally increased concentrations of these compounds in the blood, that there is a retention of amines in patients with renal diseases. On the other hand, Holtz and Credner demonstrated in fourteen patients with a nephritic hypertension that the intravenous injection of dopa resulted in a slight excretion of 3-hydroxy-tyramine or none at all. In eight healthy subjects with normal renal and circulatory functions, however, the injection of dopa produced a significant quantity of hydroxytyramine in the urine. An abnormally decreased excretion of substances which are normally voided in the urine leads to their concentration in the blood and tissues and a vicious circle is therefore set up. Thus the retained and renally active amines maintain or may even intensify the renal insufficiency reducing the renal blood supply, the glomerular filtration, and the minute volume of the urine to such an extent that they are neither metabolized nor excreted. 

Tocher RD, Tocher CA (1969) Biosynthesis of 3-hydroxy tyramine in plants Enz. In Dopa decarboxylaze XI. In International Botanical Congresse, University of Washington, Seattle, WA, USA, August 24—September 2, 1969... 

In the course of a study of the conversion of tyramine to hydroxy-tyramine by adrenal medullary homogenates, Udenfriend and his co-workers (106,769) observed t t nonspecific nonenzymic hydroxylation occurs in the presence of oxygen, ascorbic acid, ferrous iron, and ethylenediaminetetraacetic acid. The products obtained from a number of aromatic compounds are mmilar to those formed in intact animals (769) (Table VII compare Table XI).. ... 

How the aliphatic monomers are incorporated into the suberin polymer is not known. Presumably, activated co-hydroxy acids and dicarboxylic acids are ester-ified to the hydroxyl groups as found in cutin biosynthesis. The long chain fatty alcohols might be incorporated into suberin via esterification with phenylpro-panoic acids such as ferulic acid, followed by peroxidase-catalyzed polymerization of the phenolic derivative. This suggestion is based on the finding that ferulic acid esters of very long chain fatty alcohols are frequently found in sub-erin-associated waxes. The recently cloned hydroxycinnamoyl-CoA tyramine N-(hydroxycinnamoyl) transferase [77] may produce a tyramide derivative of the phenolic compound that may then be incorporated into the polymer by a peroxidase. The glycerol triester composed of a fatty acid, caffeic acid and a>-hydroxy acid found in the suberin associated wax [40] may also be incorporated into the polymer by a peroxidase. 

Tyramine (4-hydroxy-phenethylamine, para-tyramine, / -tyramine) A phenolic amine CgHnNO, a monoamine compound derived from the amino acid tyrosine. 

Tyramine is derived by using 4-hydroxybenzaldehyde as the starting material. Vanillin and 0-vanillin can also be used in this synthesis to make the tyramine analogs 2-hydroxy-3-methoxy-B-phenylethylamine and 3-methoxy-4-hydroxy-B-phenylethylamine, respectively. Vanillin is less suspicious to purchase and the potency and elfects of the vanillin made drug are about the same as Tyramine. 

MAO is a much less discriminating enzyme in that it will catalyze the removal of an amine group from a variety of substrates. The action of MAO on norepinephrine and epinephrine also is indicated in Figure 9.5. The list of its substrates is very large, including endogenous substances (norepinephrine, epinephrine, dopamine, tyramine, 5-hydroxy-tryptamine) and many drugs that are amines. At least in the brain, two separate forms of MAO have been described MAO type A and MAO type B. The two types are differentiated on the basis of substrate and inhibitor specificity. 

Fig. 30-27). The fact that L-tryptophan has some antidepressant activity, but L-dopa does not, was one clue that a low concentration of serotonin (5-hydroxy-tryptamine) might be responsible for depression. Excessive formation of histamine1099 and decreased formation of tyramine and octopamine1100 have also been suggested as causes of depression. 

From Habranthus brachyandrus habranthine (155) (mp 198-199° [ ]-5d — 320°) has been isolated in 0.006% yield. Its gross structure has been initially determined by converting (155) via hydrogenation, thionyl chloride treatment, and LiAlH4 reduction into deoxylycoramine (154). The NMR spectra of the alkaloid and of its 0,0-diacetate pointed to the structure 155 with a hydroxy group 3 to the nitrogen atom in the tyramine-derived moiety of the molecule. Indeed, the protons at C-3 and C-12 appeared as triplets at 4.10 and 3.43 ppm in the spectrum of the base and at 5.30 and 4.88 ppm in that of the diacetyl derivative. 

In Clivia miniata, O-methylnorbelladine (343) carrying 3H labels ortho to the phenolic hydroxy group of the tyramine-derived part and reference labels elsewhere is incorporated into lycorine and clivonine with the loss of both the 3H atoms. To explain this result, which contrasts with the previous one in daffodils (95), feeding experiments with [2/3-3H 5-14C]norpluviine (10) and [2a-3H 5-14C]caranine (2) were devised. The first precursor was isolated from daffodil in separate... 

The Rutaceae oxazoles are evidently derived from /V-nicotinoyl-p-(p-hydroxy)-phenylethylamide (51), with the exception of balsoxin (25) and texamine (26) in which the nicotinoyl moiety is replaced by benzoyl. The condensation of these tyramine and nicotinic acid residues does not represent any major departure from the standard routes of alkaloid biosynthesis in the Rutaceae, for it has long been recognized that the alkaloids of this family are all derived from either phenylalanine (52), tyrosine, (53), or anthranilic acid (54) (22), the latter being the acknowledged precursor to nicotinic acid in most organisms (23). The formation of the putative oxazole precursor 51 or its equivalent therefore constitutes a convergence of the two predominant modes of alkaloid biosynthesis in the family. 

Fig. 5.7. GC separation of acetone Schiff base-TMS derivatives of amines. Peaks 1 = (3-phenylethyl-amine 2 = norephedrine 3 = (J-hydroxy-0-phenylethylamine 4 = tyramine 5 = 0-(3,4-dimethoxy-phenyl)ethylamine 6 = metanephrine 7 = dopamine 8 = epinephrine 9 = normetanephrine 10 = norepinephrine. Conditions glass column, 6 ft. x 4 mm I.D., 10% F-60 on Gas-Chrom P (80-100 mesh, AW, silanized) nitrogen inlet pressure, 12 p.s.i. temperature programme, 1.5°C/min. (Reproduced from Anal. Chcm., 38 (1966) 316, by courtesy of E.C. Horning and the American Chemical Society.)...

Tyramine (= 4-Hydroxy- (Myrtaceae), Pirns (Pinaceae), Artocarpus, Morus (Moraceae), Polygonum (Polygonaceae), Vitis (Vitaceae) spp. glycosides in Polygonum (Polygonaceae), Angophora, Eucalyptus (Myrtaceae) spp. Lophophora uilliamsi, Trichocereus Precursor of... 

The relation of many of the simpler alkaloids to the aromatic amino acids is obvious. For example, germinating barley contains (241), besides tyrosine and tyramine, A -methyltyramine, JViV -dimethyltyramine (hordenine), and the trimethylammonium derivative (candicine). In this simple case the. AT-methylated derivatives are known to be derivable from isotopically labeled tyramine (538) and the methyl groups are known to arise from methionine by transmethylation (540, 586). Similarly AT-methyl derivatives of phenylethylamine, 3,4-dihydroxyphenylethylamine, and 3,4,5-trihy-droxyphenylethylamine are well known alkaloids (cf. review, 701). N-Methylated derivatives of tryptamine and hydroxytryptamine equally occur for example, eserine has an obvious relation to 5-hydroxy tryptamine. Methylated derivatives of metabolites of the aromatic amino acids also occur, for example, trigonelline (67), which is the betaine of nicotinic acid, and damascenine is probably similarly related to hydroxyanthranilic acid. 

Protoalkaloids are bases with a simple structure, e.g. the biogenic amines, which are formed by decarboxylation or N-methylation of an amino acid (tyramine, histamine, choline, ephedrine, mescaline). Capsaicin, which is the amide of vanillylamine (4-hydroxy-3-methoxybenzylamine), has also been included in this group. 

In the biogenesis of the peptide alkaloids the major point of interest is the way in which the macrocycle is closed. There is as yet no evidence, but one suspects that one of the bonds to the ether oxygen is formed last. Since the precursor of the tyramine unit in these bases is doubtless p-hydroxyphenylalanine, the ring might be closed by conjugate addition of the phenolic hydroxy-group to an unsaturated amide of the lasiodine-A (8) type, or perhaps by conjugate addition of an oxidised p-hydroxyphenylalanine unit to an unsaturated amide (12). The... 

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