Trypt amine

The second line of circumstantial evidence quoted in support of this hypothesis is the ready formation of l,2,3,4-tetrahydro-/3-carboline derivatives under pseudo-physiological conditions of temperature, pH, and concentration. Tryptamine and aldehydes, trypt-amine and a-keto acids, and tryptophan and aldehydes condense at room temperature in a Pictet-Spengler type intramolecular Mannich reaction in the pH range 5.2-8.0 (cf. Section III, A, 1, a). It was argued that experiments of this type serve as models for biochemical reactions and may be used in evidence. 

Based on the foregoing discussion, it is possible to formulate some structure-activity relationships with respect to the behavioral properties of various trypt-amine derivatives. It should be noted that these structure-activity relationships are derived from the results of both human and animal studies. 

Trubitsyna, T. K., and Mashkovskii, M. D. (1970) Pharmacological properties of some trypt-amine analogs. Farmakol. Toksikol., 33 387-392. 

Skillen, R. G., C. H. Thienes, J. Cangelosi, and L. Strain. Lung 5-hydroxy-trypt-amine and ozone induced pulmonaiy edema in rats. Proc. Soc. Exp. Biol. Med. 107 178-180, 1%1. 

The enzyme responsible for the stereospecific condensation of trypt-amine and secologanin 34) was called strictosidine synthase, and its presence was demonstrated by Treimer and Zenk 194) in a number of indole alkaloid-producing plants, including Amsonia salicifolia, Catharanthus roseus, Ochrosia elliptica, Rauwolfia vomitoria, Rhazya orientalis, Stem-madenia tomentosa. Vinca minor, and Voacanga africana. Enzyme activity as high as 1698 pkat/mg protein was observed for O. elliptica. No... 

MAO A and B differ in primary structure and in substrate specificity [5,7]. The two isozymes, located on the mitochondrial outer membranes, have 70% homology in peptide sequence and share common mechanistic details. It is now recognized that these are different proteins encoded by different genes, but probably derived from a common ancestral gene. Crystal structures for both MAO A and B complexes with inhibitors have recently been reported [8]. Serotonin is selectively oxidized by MAO A, whereas benzylamine and 2-phenylethylamine are selective substrates for MAO B. Dopamine, norepinephrine, epinephrine, trypt-amine, and tyramine are oxidized by both MAO A and B in most species [9]. In addition, MAO A is more sensitive to inhibition by clorgyline (1), whereas MAO B is inhibited by low concentrations of L-deprenyl ((f )-( )-deprenyl) (2) [5,6cj. Development of inhibitors that are selective for each isozyme has been an extremely active area of medicinal chemistry [8]. 

B. Newman, V. T. Sullivan, and A. Dihrberg, Thin-layer chromatography of lysergic acid diethylamide (LSD), iV,N-dimethyl trypt-amine (DMT), methylene dioxyphenyl isopropylamine (STP), and ibogaine, J. Crim. Law Criminol., 61 112 (1970). 

HO-MET TRYPT AMINE, N-ETHYL-4-HYDROXY-N-METHYL 4-INDOLOL, 3- 2-(ETHYLMETHYLAMINO)ETIIYL] N-ETHYL-4-HY-DROX Y-N-METHYLTRYPT AMINE 3-[2-(ETHYLMETHYLAMINO)-ETHYL]-4-INDOLOL... 

HO-pyr-T TRYPT AMINE,4-HYDROXY-N,N-TE TRAMETH-YLENE 4-INDOLOL,3-[2-(l-PYRROLIDYL)ETHYL] PYRROLIDINE, l-[2-[3-(4-HYDROXY)INDOLYL]ETHYL] 4-HYDROXY-N,N-TETRA-METHYLENETRYPTAMINE 3-[2-(l-PYRROLIDYL)ETHYL]-4-INDOLOL l-[2-[3-(4-HYDROXY)INDOLYL]ETHYL]PYRROLIDINE 4-HYDROXYPYRROLIDYLTRYPT AMINE ... 

MDO-DIPT TRYPTAMINE, N,N-DIISOPROPYL-5,6-METHYLENEDIOXY INDOLE, 3-[2-(DIISOPROPYLAMINO)ETHYL]-5,6-METHYLENEDIOXY NJ -DIISOPROPYL-5,6-METHYLENEDIOXY-TRYPT AMINE 3-[2-(DIISOPROPYLAMINO)ETHYL]-5,6-METHYL-ENEDIOXYINDOLE 5H-l,3-DIOXOLO-[4,5-F]INDOLE-7-ETHANE-AMINE, N,N-DIISOPROPYL... 

Several syntheses are on record which avoid the preparation of 5-benzyloxyindole in these procedures, the indole ring is usually formed after provision is made for the introduction of the ethanamine side chain. The first of these (107, 108) was an adaptation of Ewins original trypt-amine synthesis. A subsequent route (109) started from ethyl a-cyano-2,5-dimethoxycinnamate (VIII), which was prepared by condensation of 2,5-dimethoxybenzaldehyde with ethyl cyanoacetate. When this was boiled with potassium cyanide solution, addition of the elements of hydrogen cyanide was accompanied by hydrolysis of the ester function and decarboxylation, to give 2,5-dimethoxyphenylsuccinonitrile (IX). 

The condensation of isocoumarincarboxylic acid (XXX) with trypt-amine gave unsatisfactory yields of the expected product, XXXI (20). 

Some of the most interesting applications of organic structural theory to the elucidation of biosynthetic pathways were stimulated by efforts to formulate mechanisms for the biosynthesis of alkaloids. Conversely, consideration of implied biogenetic relations have occasionally helped structural determination. An important aspect of theories concerning alkaloid biosynthesis has been the assumed role of the aromatic amino acids in their formation. Only limited experimental evidence is available in this area. The incorporation of tyrosine- 8-C into morphine has been shown to be in accordance with a theory for its formation from 3,4-dihydroxyphenyl-alanine plus 3,4-dihydroxyphenylacetaldehyde. A stimulating theory of the biosynthesis of indole alkaloids, based on a condensation between trypt-amine and a rearrangement product of prephenic acid, has recently been published. The unique stereochemistry of C15 of these alkaloids had an important part in the formulation of the theory. Experimental proof of this theory would be valuable for several areas of alkaloid chemistry and biosynthesis. 

Strictosidine synthetase catalyzes the stereospecific condensation of trypt-amine and the iridoid glucoside secologanin to form strictosidine. The product is the precursor of the monoterpenoid-derived indole and quinoline alkaloids. 

Hoi ms tedt et al. applied gas chromatography to solve the problem of the structure of the chief indole bases of epeni, a South American snuff reported to produce hallucinations. With the gas chromatographic method mentioned above the following compounds were found Trypt-amine, N,N-dimethyltryptamine, 5-hydroxy-tryptamine, 4-hydroxy-N,N-dimethyltryptamine, 5-hydroxy-N,N-dimethyltryptamine, 6-hydroxy-N,N-dimethyltryptamine and 7-hydroxy-N,N-dimethyl tryptamine. 

Nguyen TV, Paterson IA, Juorio AV, Greenshow AJ, Boulton AA (1989) Trypt-amine receptors neurochemical and electrophysiological evidence for post-synaptic and functional binding sites. Brain Res 476 85-93... 

Later, a modified version of the synthesis was reported, in which the important secodine precursor is a tetrahydro-jS-carboline derivative, such as 557-559, rather than an indoloazepine ester, as in 560. This led to a simpler synthesis, the tetrahydro-/3-carboline derivatives required for the preparation of 557-559 being obtained directly from the appropriate trypt-amine derivative and pyruvic acid ester. By this route, ( )-vincadifformine (76), ( )-minovine (A g-methylvincadifformine) and ( ) ervinceine (87) were synthesized in comparatively high yield, and in essentially two stages from the starting tryptamine (330). 

Following their recent synthesis of ( )-vincadifformine (Scheme 75) (343,344), Szantay and his collaborators have contributed another s3mthesis of pseudovincadifformine and its epimers (392). Condensation of the trypt-amine derivative 587 with the aldehydoester 698 gave, via an unstable secodine derivative, the epimeric tetracyclic esters 715, which, without separation, were subjected to debenzylation, with partial epimerization and cyclization. The product, a mixture of the two cis C/D-fused pentacyclic... 

Recently, a LC/ESI-MS method for analysis of tyramine, trypt-amine, 2-phenylethylamine, histamine, cadaverine, putrescine, spermidine, and spermine in wine without any sample pretreatment, was... 

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