Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Tryptamines”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,117 records · Page 62Linked to original sources
PubMed1982

Increased fluidity of a model membrane caused by tetrahydro-beta-carbolines.

Alterations in membrane fluidity caused by alcohols and tetrahydro-beta-carbolines (THBCs) have been studied. Dipalmitoylphosphatidylcholine vesicles were used as a membrane preparation, and changes in the fluidity were revealed by two fluorescent probes: 1-anilinonaphthalene-8-sulfonic acid (1,8-ANS) and N-phenylnaphthylamine (NPN). It was found that THBCs, which are condensation products of tryptamine and formaldehyde or acetaldehyde, were at least 2 orders of magnitude more potent in causing fluidity changes than the comparable alcohols (methanol and ethanol). Both 1,8-ANS (binding close to the polar end of the phospholipid molecules) and NPN (binding to the hydrophobic region of the membrane) were able to reveal changes in membrane fluidity, although there were differences between the behavior of the two probes. The condensation product of acetaldehyde--the primary metabolite of ethanol--and tryptamine were found to be 200-300 times more potent in causing fluidity changes than ethanol itself (as determined with both 1,8-ANS and NPN).

Anilino Naphthalenesulfonates↗
PubMedDate not supplied

[Changes in alcohol choice by chronically alcoholized cats as affected by tryptopham, its metabolites and preparations affecting its metabolism].

In cats unrestrictedly selecting alcohol and water during 5 months - 4.5 years under normal feeding, intraperitoneal injection of 1-tryptophan (5.5 and 65 mg/kg) lowered alcohol intake. Depending on the effect on water intake, a decrease (after a lower dose) or an increase (after a higher dose) in alcohol preference was observed. Tryptophan metabolites (mg/kg): dl-5-hydroxytryptophan (5-HTP, 6 and 12), tryptamine (2.5 and 5), 1-4 and dl-(2 and 6)kynurenine, as well as drugs modifying tryptophan metabolism, such as Ro-4-4602(2), an inhibitor of peripheral decarboxylase of aromatic amino acids, and allopurinol (2), an inhibitor of tryptophan pyrrolase (10 and 17), enhanced alcohol intake. Preference of alcohol was increased after tryptamine and 1-kynurenine and decreased after 5-HTP administration. Control injections of saline and distilled water resulted in a significant increase in alcohol and water intake. Saline increased preference of alcohol.

Absorption↗
PubMed1980

Serotonin receptors subserve only contraction in canine and rat pulmonary arteries and veins.

Precise information with respect to whether serotonin (5-HT) exerts direct effects on mammalian pulmonary arteries and veins is lacking. The present studies, using isolated pulmonary arterial strips of dogs and rats, as well as isolated pulmonary veins of dogs, indicate that serotonin exerts direct contractile, but not relaxant, effects on these blood vessels. Contractile responses to 5-HT were not influenced by "specific" receptor-blocking doses of pyrilamine (H1-receptor antagonist), metiamide (H2-receptor antagonist), phentolamine (alpha-adrenoceptor antagonist), propranolol (beta-receptor antagonist), atropine (cholinergic antagonist) or morphine ("M" tryptamine antagonist). These data demonstrate the lack of interaction of 5-HT with either H1- and H2-histamine, alpha and beta-adrenergic, cholinergic, or "M" tryptamine receptors in these pulmonary blood vessels. Selective, competitive antagonism of 5-HT-induced contractions by methysergide (parallel shifts of concentration-effect curves) demonstrate a direct action of 5-HT on D-type serotonin receptors in these pulmonary blood vessels.

Animals↗
PubMed1996

Histological localization of messenger RNAs for rat acetyltransferases that acetylate serotonin and genotoxic arylamines.

Rat acetyltransferases (ATs) can acetylate the endogenous arylalkylamines tryptamine, 5-hydroxytryptamine (serotonin), and 5-methoxytryptamine, the immediate precursor of melatonin. The same enzymes also acetylate and activate exogenous, carcinogenic arylamines, thereby being immediately responsible for the generation of DNA adducts. Localization of AT transcripts in the pineal gland and in specific cells of the intestine, cerebral cortex, pituitary, and lung identifies cells that may be important to the neurotransmitter and hormonal roles of the tryptamine derivatives. Transcript localization i liver, mammary gland, Zymbal gland, kidney, forestomach, and bladder, as well as intestine and lung, identifies cells that may be at increased carcinogenic risk because they can convert N-hydroxylated arylamines to genotoxic metabolites. Highly specific expression is also observed in the reproductive organs of both the male and female, including the testes, epididymis, uterus, ovary, and fallopian tube. In addition to these diverse organs, which are consistent with possible roles of the enzyme in carcinogen metabolism, neurotransmission, or hormonal regulation, specific cells of the cornea, cilliary process of the eye, olfactory process, adrenal gland, exorbital lacrimal gland, and skin also exhibit highly specific expression of AT mRNAs for which one can only speculate as to their function. In virtually every case, the extent of labeling suggested that AT1 was expressed at levels that were orders of magnitude higher than those of AT2. Qualitative differences in the sites of mRNA of these two enzymes were seen only in the olfactory process, in which AT1 was expressed in both respiratory and olfactory epithelia as well as Bowman's cells, and AT2 was detected only in the latter cells. The available data support the conclusion that the ATs are likely to be involved both in the metabolic activation of exogenous carcinogenic amines as well as the metabolism of endogenous arylalkylamines that play important hormonal and neurotransmitter roles.

Acetylation↗
PubMed1977

[Properties of mitochondrial monoamine oxidase isolated from rabbit brain and liver].

The effect of pO2 on the monoamine oxidase activity of mitochondria from rabbit brain and liver was investigated using the substrates tyramine, dopamine, tryptamine and serotonin. The effect of the second substrate (oxygen) was dependent upon the concentration of the first substrate (the amine). At amine concentrations below 50 micronM, the reaction rate as measured by a radiometric assay, was not affected by variations in the pO2. It was found that both phenazine methosulfate (PMS) and chlorpromazine (CPZ) are reversible inhibitors of monoamine oxidase, the former was a potent inhibitor (Ki=3X10(-6) M) and the latter relatively weak (Ki=5X10(-4) M). Inhibition by both compounds was non-competitive with respect to the amine substrate. Imipramine was a weak inhibitor of purified MAO from beef kidney and of the MAO activity of mitochrondria from brain and liver. Using tyramine or dopamine as the substrate (0.5-1.0 mM), inhibition ranging from 6-30% was observed at 5X10(-4) M imipramine. With tryptamine or serotonin (0.5-1.0 mM) as the substrate in the presence of 5X10(-4) M imipramine the drug seemed to have no net effect on MAO activity since the average value in the presence of imipramine for a number of experiences was the same as the average for control experiments. For p-iodo-phenyl-3-p-nitrophenyl tetrazolium chloride, a Ki of 43X10(-6) M was found using dopamine as the substrate and oxygen as the gas phase.

Animals↗
PubMed1993

Induction of ajmalicine formation and related enzyme activities in Catharanthus roseus cells: effect of inoculum density.

In Catharanthus roseus cell cultures the time courses of four enzyme activities, tryptophan decarboxylase (TDC), strictosidine synthase (SSS), geraniol-10-hydroxylase (G10H) and anthranilate synthase (AS), and alkaloid accumulation were compared under two different culture conditions (low-inoculum density and high-inoculum density on induction medium) and a control on growth medium. In growth medium a transient increase in TDC activity was first observed after which G10H reached its maximum activity; only tryptamine accumulated, no ajmalicine could be detected. Apparently, a concerted induction of enzyme activities is required for ajmalicine formation. Cells inoculated in induction medium showed such a concerted induction of AS, TDC and G10H activities. After 30 days the low-density culture had accumulated six times more ajmalicine (in mumoles/g) than the high-density culture. Thus, increase in biomass concentration (high-density cultures) did not enhance the total alkaloid production. The major differences observed in enzyme levels between high- and low-density cultures were in the AS and TDC activities, which were two to three times higher in the low-density culture, indicating that there is a positive correlation between ajmalicine formation and AS and TDC activities.

Acyclic Monoterpenes↗
PubMed2001

Effects of stress factors, bioregulators, and synthetic precursors on indole alkaloid production in compact callus clusters cultures of Catharanthus roseus.

Compact callus cluster (CCC) cultures established from Catharanthus roseus consist of cohesive callus aggregates displaying certain levels of cellular or tissue differentiation. CCC cultures synthesize about two-fold more indole alkaloids than normal dispersed-cell cultures. Our studies here show that additions of KCl, mannitol, and a variety of synthetic precursors and bioregulators to the CCC cultures markedly improved indole alkaloid production and release of these alkaloids into the medium. Treatment with 250 mM mannitol and 4 g/l KCl yielded 42.3 mg l(-1) and 33.6 mg l(-1)of ajmalicine, respectively; these amounts were about four-fold higher than the control. Succinic acid, tryptamine, and tryptophan feedings also significantly increased ajmalicine (41.5 mg l(-1), 36.9 mg l(-1), and 31.8 mg l(-1), respectively) and catharanthine (21.1 mg l(-1), 17.2 mg l(-1), and 18 mg l(-1), respectively) production by the CCC cultures, while geraniol feeding inhibited biomass and alkaloid accumulation. We also found that tetramethyl ammonium bromide could significantly improve ajmalicine production (49.3 mg l(-1)) and catharanthine production (18.3 mg l(-1)) in C. roseus CCC cultures. The mechanisms responsible for these treatment effects are discussed herein.

Acyclic Monoterpenes↗
PubMed1964

SOME PHARMACOLOGICAL PROPERTIES OF THIOPROPERAZINE AND THEIR MODIFICATION BY ANTI-PARKINSONIAN DRUGS.

The pharmacological properties of a phenothiazine derivative thioproperazine have been compared with those of chlorpromazine, and the modifications by some anti-Parkinsonian drugs of its actions on the central nervous system have been studied. Thioproperazine was less potent than chlorpromazine in lowering blood pressure and antagonizing adrenaline in the cat, in depressing respiratory rate in the rabbit, in producing hypothermia and analgesia and in reducing the minimum anaesthetic dose of hexobarbitone in mice, and in protecting rats from convulsions induced by tryptamine. It was roughly equipotent to chlorpromazine in reducing locomotor activity of mice. Thioproperazine was more potent than chlorpromazine in protecting grouped mice from the acute toxicity of dexamphetamine, in preventing the acute behavioural disturbances produced by dexamphetamine in the rat, in producing a state of experimental catatonia in the rat and in preventing the emetic action of apomorphine in the dog. Hyoscine, benztropine or promethazine greatly reduced the ability of thioproperazine to prevent behavioural changes due to dexamphetamine in the rat and also abolished symptoms of experimental catatonia produced by thioproperazine. In contrast, the antiapomorphine activity of thioproperazine in the dog was not reduced to any extent by hyoscine or benztropine.

Anesthetics↗
PubMed1964

A COMPARISON OF PLATELET AGGREGATION PRODUCED BY SEVEN COMPOUNDS AND A COMPARISON OF THEIR INHIBITORS.

The aggregating effects of adenosine diphosphate, thrombin, 5-hydroxytryptamine, tryptamine, adrenaline and noradrenaline, and tri-ethyl tin have been carefully compared. The first three compounds in some circumstances produce remarkably similar effects although there are important differences. The kinetics of aggregation induced by adrenaline (and noradrenaline) are quite different and the tri-ethyl tin effects are different again. Anti-serotonins specifically inhibit 5-hydroxytryptamine and the anti-adrenaline drug phentolamine specifically inhibits the effects of the catecholamines. Experiments presented suggest but do not prove that aggregation produced by all these compounds is accompanied by the liberation of diphosphate from the platelets and that platelet triphosphate may be converted to diphosphate. How these different compounds all produce this effect is discussed. Either the presence of diphosphate or the action of a triphosphatase might be the immediate cause of aggregation if there is a single final common cause. The anti-adrenaline phentolamine prolongs the bleeding time, so adrenaline or noradrenaline may be involved in platelet phenomena in haemostasis.

Adenine Nucleotides↗
PubMed2005

[Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].

Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine which are biosynthesized via strictosidine, an alkaloidal glucoside, formed from secologanin and tryptamine. In secologanin biosynthesis, the oxidative cleavage process of loganin to secologanin and the hydroxylation of 7-deoxyloganin to loganin have remained unknown enzymologically and mechanistically. Cornoside is a unique glucoside with 4-hydroxy-2,5-cyclohexadien-1-one (benzoquinol) ring and is widespread in families such as Cornaceae, Oleaceae, and Scrophulariaceae but its biosynthesis, especially the oxidative process, remain to be investigated. Shikonin is a red naphthazarin pigment derived from the roots of Lithospermum erythorhizon and produced biotechnologically by cell cultures. Its biosynthesis including the production regulation mechanism has been investigated in detail. However, the naphthazarin ring formation process, probably starting with the hydroxylation of the side chain of geranylhydroquinone, a key intermediate at the late stage of shikonin biosynthesis, remained unknown. In the present review, cytochrome P450 monooxygenases involved in the biosyntheses of three structurally and biosynthetically interesting compounds, secologanin, cornoside, and shikonin, a described together with the results of previous and recent biosynthetic studies. The biosyntheses of related compounds are also discussed.

Cyclohexanones↗
PubMed1976

Platelet monamine oxidase in chronic schizophrenia. Some enzyme characteristics relevant to reduced activity.

To evaluate further the basis for the reduced activity of platelet monoamine oxidase (MAO) found in chronic schizophrenic patients, a number of characteristics of the enzyme were compared between patients and controls. Equivalent and statistically significant reductions in activity of the enzyme were found in the patients when tyramine and benzylamine were used as the substrates in comparison to previously reported reductions with tryptamine as the substrate. Michaelis constants for platelet MAO from chronic schizophrenic patients with reduced enzyme activity were not different from controls. Dialysis of the enzyme from patients and controls yielded no changes in activity. Studies of other platelet enzymes, including succinate dehydrogenase, cytochrome C reductase, and lactate dehydrogenase in patients, normal controls, and a subgroup of normal controls with reduced MAO activity, showed no parallel reductions in activity in patients or controls with low MAO activity. These findings suggest that the reduced MAO activity found in chronic schizophrenic patients is apparently not accounted for by nonspecific changes in platelets or platelet mitochondria.

Adult↗
PubMed1977

Hyperserotonemia and amine metabolites in autistic and retarded children.

Mean whole blood serotonin (5-HT) levels were elevated in groups of autistic and severely retarded children. Eight of 27 (30%) individual autistic children, 13 of 25 (52%) severely retarded children, two of 23 (9%) mildly retarded children, and none of the control children had statistically significant blood 5-HT levels elevations (hyperserotonemia). Hyperserotonemic autistic children excreted more urinary 5-HT, 5-hydroxyindoleacetic acid (5-HIAA), tryptamine, and vanillylmandelic acid than did mildly retarded children with normal blood 5-HT levels. Rates of depletion and repletion of blood 5-HT levels in these two groups following reserpine therapy were identical. Oral tryptophan administration doubled urinary 5-HIAA excretion in both groups and raised urinary 5-HT levels in hyperserotonemic autistic children, but lowered urinary 5-HT in mildly retarded, normal blood 5-HT children. No clear mechanism for hyperserotonemia was found; the rationale for further investigations is discussed.

Adolescent↗
PubMed2006

Effects of terpenoid precursor feeding on Catharanthus roseus hairy roots over-expressing the alpha or the alpha and beta subunits of anthranilate synthase.

Among the pharmacologically important terpenoid indole alkaloids produced by Catharanthus roseus are the anti-cancer drugs vinblastine and vincristine. These two drugs are produced in small yields within the plant, which makes them expensive to produce commercially. Metabolic engineering has focused on increasing flux through this pathway by various means such as elicitation, precursor feeding, and introduction of genes encoding specific metabolic enzymes into the plant. Recently in our lab, a feedback-resistant anthranilate synthase alpha subunit was over-expressed in C. roseus hairy roots under the control of a glucocorticoid inducible promoter system. Upon induction we observed a large increase in the indole precursors, tryptophan, and tryptamine. The current work explores the effects of over-expressing the anthranilate synthase alpha or alpha and beta subunits in combination with feeding with the terpenoid precursors 1-deoxy-D-xylulose, loganin, and secologanin. In feeding 1-deoxy-D-xylulose to the hairy root line expressing the anthranilate synthase alpha subunit, we observed an increase of 125% in hörhammericine levels in the induced samples, while loganin feeding increased catharanthine by 45% in the induced samples. Loganin feeding to the hairy root line expressing anthranilate synthase alpha and beta subunits increases catharanthine by 26%, ajmalicine by 84%, lochnericine by 119%, and tabersonine by 225% in the induced samples. These results suggest that the terpenoid precursors to the terpenoid indole alkaloids are important factors in terpenoid indole alkaloid production.

Anthranilate Synthase↗
PubMedDate not supplied

Therapeutic doses of cyproheptadine do not inhibit monoamine oxidase in man.

Cypro, a serotonin and histamine antagonist, has been shown to be a moderately potent reversible inhibitor of tissue monoamine oxidase (MAO) obtained from hamsters and rabbits. In the present study, Cypro inhibits MAO obtained from human platelets with the same potency as harmine (Ki = 5 x 10(-5) M). However, when ten normal volunteers received conventional therapeutic doses of Cypro (16 mg/day) for two days, there was no alteration in their urinary excretion of tryptamine, 5-hydroxyindoleacetic acid, 3-methoxy-4-hydroxymandelic acid, epinephrine, or norepinephrine. We conclude that, when used in conventional clinical doses, Cypro does not inhibit MAO in man.

Adult↗
PubMed1994

Quantitation of urinary 1,2,3,4-tetrahydro-beta-carboline and 1-methyl-1,2,3,4-tetrahydro-beta-carboline by high-performance liquid chromatography.

A high-performance liquid chromatographic method was developed to quantify 1,2,3,4-tetrahydro-beta-carboline (TBC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline (MTBC) in human urine. Urine samples with added internal standard were subjected to a reaction with fluorescamine and solvent extractions to remove the precursor tryptamine, which readily condenses with aldehydes in samples and reagents. Such a pretreatment completely suppressed the artifactual formation of TBC and MTBC during analytical procedures. The purified original tetrahydro-beta-carbolines and the internal standard were separated by reversed-phase ion-pair chromatography with fluorescent detection. Their simultaneous separation was automatically completed in a short time (< 12 min). Both TBC and MTBC were quantified at ng/mL concentrations. The quantitative results revealed a wide variation in urinary levels of TBC and MTBC, possibly indicating that their considerable amounts excreted in the urine originate from dietary sources.

Adolescent↗
PubMed2002

Characterisation and determination of indole alkaloids in frog-skin secretions by electrospray ionisation ion trap mass spectrometry.

The characterisation of selected indole alkaloids in a quadrupole ion trap mass spectrometer is presented. Fragmentation profiles for tryptamine, 5-hydroxytryptamine (5-HT), N'-methyl 5-hydroxytryptamine (N'-methyl 5-HT), N',N'-dimethyl 5-hydroxytryptamine (bufotenine), N',N',N'-trimethyl 5-hydroxytryptamine (5-HTQ), and N',N'-dimethyl 5-methoxytryptamine (5-MeODMT) are presented with proposed structures given for each product ion observed. Such MS(n) experiments can be used to differentiate the isobaric molecular ions of the compounds 5-HTQ (M(+)) and 5-MeODMT (MH(+)). The quantitative determination of certain indole alkaloids in the skin secretions of the Australian Golden Bell frog, Litoria aurea, by LC/ESI-ion trap MS is also presented. The concentrations of 5-HT, N'-methyl 5-HT and 5-HTQ were found to be 2.68, 0.26 and 0.54 microg per mg of skin secretion, respectively.

Alkaloids↗
PubMed1993

N-bromoacetyl 5-methoxytryptamine: an irreversible melatonin ligand?

The effects of N-bromoacetyl 5-methoxytryptamine (BraMT) and some related bromoacyl melatonin and tryptamine derivatives on 2-[125I]iodomelatonin (2-[125I]aMT) binding in chicken brain membranes were examined. All analogues displaced specific binding to chicken brain membranes in a concentration-dependent manner. Preincubation of chicken brain membranes with BraMT (10(-8)M) did not significantly alter either 2-[125I]aMT binding site affinity (Kd) or density (Bmax). SDS polyacrylamide gel electrophoresis of chicken brain membrane proteins preincubated with 2-[125I]BraMT indicated that numerous proteins were labelled. The incorporation of radiolabel into these proteins was not blocked by melatonin, 2-iodomelatonin or N-(1,4 dinitrophenyl)-5-methoxytryptamine (ML-23), but was reduced by BraMT. In contrast to previous reports on hamster and rat brain membranes, the present results provide no evidence that BraMT or 2-[125I]BraMT affinity labels specific melatonin binding proteins in chicken brain.

5-Methoxytryptamine↗
PubMed1994

Melatonin inhibits LDL receptor activity and cholesterol synthesis in freshly isolated human mononuclear leukocytes.

There is some indirect evidence that the pineal hormone melatonin can suppress plasma levels of cholesterol in hypercholesterolemic rats. We have examined the effects of the hormone on cellular cholesterol metabolism in freshly isolated human mononuclear leukocytes. Incubation of cells for up to 20 h in a lipid-free medium resulted in an increase in the rate of cholesterol synthesis from [14C]acetate and the high affinity accumulation and degradation of [125I]labeled low density lipoprotein (LDL). Addition of melatonin in increasing concentrations to the incubation medium at zero time inhibited cholesterol synthesis and the specific accumulation and degradation of [125I]labeled LDL; at a concentration of 100 microM, the inhibitions were 38%, 42%, and 48%, respectively. Similar results were obtained using [14C]mevalonate as precursor. Fatty acid synthesis was not altered under these conditions. In contrast to cholesterol, the synthesis of the first cyclic compound lanosterol was not affected by the pineal hormone. These results implicate that melatonin inhibits this pathway between lanosterol and cholesterol. The action of melatonin on LDL receptor activity appeared to be mediated by a decrease in the number of LDL receptors and not by a change in binding affinity. Pharmacological characterization of the potential melatonin receptor site using several analogs like tryptamine, 5-hydroxytryptamine,N-acetyl-5-hydroxytryptamine, 5-methoxytryptamine, and 6-chloromelatonin indicated that the 5-methoxy group is indispensible for the hormone action on cholesterol synthesis. The data provide evidence that melatonin can modulate cholesterol metabolism in human cells.

5-Methoxytryptamine↗