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PubMed1975

Neurochemical evidence for tryptaminergic ascending and descending pathways in the spinal cord of the dog.

The brain and spinal cord of the chronic spinal dog contained higher levels of tryptamine than comparable regions of the intact dog. The most significant brain elevations were found in the cerebellum and mesencephalon. Further, tryptamine in the white matter of the spinal cord above the level of transection was higher than below. These findings have been interpreted as indicating that there are tryptaminergic pathways descending in the white matter of the spinal cord from the mesencephalon, cerebellum and rostral spinal cord. The level of tryptamine below the transection was not different from that found in the intact dog, suggesting that there are not only descending but ascending tryptaminergic pathways and that when the axons are transected. tryptamine accumulates proximal to the level of transection.

Afferent Pathways↗

PubMed1980

Inhibition of ionic transport and ATPase activities by serotonin analogues in the isolated toad lens.

The effects of serotonin and five other indoles were tested on the electrical parameters and ionic transport in the isolated toad lens. Serotonin, tryptophan and 5-hydroxy-L-tryptophan did not affect the electrical parameters of the lens at concentrations as high as 1 mM. Tryptamine, 5-methyltryptamine and 5-methoxytryptamine had dual effects: 1 mM in the posterior bathing solution depressed the potential difference of the posterior face of the lens, which resulted in an increase in the translenticular potential difference and short-circuit current; 1 mM in the anterior solution (in contact with the lens epithelium) produced a quick and pronounced reduction of the potential difference of the anterior face. This resulted in a 90-100% decline of the translenticular short-circuit current. Serotonin and tryptamine were then tested for their effect on the ATPases of lens epithelium. Both amines inhibited the enzymes with tryptamine at 5 mM completely inhibiting all ATPase activity. Since tryptophan is transported from the aqueous humor into the lens and may be converted by lens enzymes to serotonin and tryptamine, these findings may have physiological implications in cataractogenesis.

5-Hydroxytryptophan↗

PubMed1995

Formation of tetrahydro-beta-carbolines in human saliva.

When human saliva obtained after cigarette smoking was incubated in the presence of tryptamine, the formation of 1,2,3,4-tetrahydro-beta-carboline (TBC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline (MTBC) was observed in a short time. After incubation with tryptamine (2.5 micrograms/microliter) for 10 min, the concentrations of TBC and MTBC formed were 3.27 +/- 0.94 and 0.35 +/- 0.17 ng/microliter, respectively. The formation of TBC and MTBC in intact saliva and in saliva heated at 100 degrees for 10 min was compared, but no significant difference was found. The analysis of foodstuffs showed that significant amounts of tryptamine were contained in various foods and beverages. The analysis of cigarette smoke solutions and immersion solutions of denture-base acrylic resins showed that ng-micrograms/microliter levels of formaldehyde and acetaldehyde were contained in cigarette smoke and leached from dental resins. These results indicate that both precursors, tryptamine and aldehydes, coexist in oral environments and that their interaction to form TBC and MTBC potentially occurs in human saliva without participation of salivary enzyme.

Adult↗

PubMed1976

Release of smooth muscle-contracting substances from isolated perfused lungs.

Infusion of tryptamine (1-4 mug/ml) through the pulmonary circulation of rat isolated lung perfused with Krebs solution caused release of a mixture of spasmogens contracting isolated smooth muscle preparations. One component of this mixture had biological activity comparable to E-type prostaglandins. Other components included a slow reacting substance comparable to SRS-A and a rabbit aorta-contracting substance comparable to RCS. Infusions of 5-hydroxytryptamine, acetylcholine and histamine (0.5-2 mug/ml) also caused release. Release induced by the tryptamines but not that by acetylcholine and histamine was prevented by methysergide whereas acetylcholine-induced release was prevented by hyoscine which did not affect tryptamine-induced release. The tryptamines and histamine released spasmogens from dog isolated lungs but only histamine was effective in guinea-pig lungs. We conclude that amine-induced release from isolated lungs is a fairly general phenomenon and that it may represent an endocrine function of lung.

Acetylcholine↗

PubMed1976

Drug antagonism and reversibility of the binding of indoleamines in brain.

The specificity of the binding of serotonin to brain preparations was investigated with various competitive agents. A probable relationship between their structure and their capability of displacement was suggested. Bufotenine and morphine displaced serotonin (0.5 X 10(-5) M) binding to synaptic membranes 87 and 49% respectively. Dissociation constants of the binding of 5-HT and tryptamine to synaptic membranes, and displacement constants of certain drugs were determined. The binding of 5-HT and tryptamine to calf brain preparations was also investigated by equilibrium dialysis, in order to determine affinity constants and reversibility of the binding. Differences were noted in the specificity of binding sites for serotonin and tryptamine, suggesting a different binding site for tryptamine. Extrapolations of Scatchard plots were used for determination of the constants. A characteristic low dissociation constant was found for 5-HT in synaptic membranes (K approximately X 10(-6) M). Probably, the binding macromolecule (receptor?) is a proteolipid.

Animals↗

PubMed1987

Biogenic amines in the Arthus reaction.

The concentrations of serotonin, tryptamine, dopamine, and tyramine were quantitatively determined in the Arthus reaction, since the activity of histamine-N-methyltransferase (HMT), a major histamine-metabolizing enzyme that had been demonstrated to be inhibited by such biogenic amines in vitro, decreased significantly in the reaction site. The concentrations of serotonin, tryptamine, and dopamine were unchanged in dinitrochlorobenzene allergic and croton oil dermatitis except for a slight increase of tryptamine in the latter. Tyramine was unable to be demonstrated quantitatively in all specimens tested. The concentration of serotonin decreased to about 30% that of the control level until 1 hr, followed by a prominent increase to about two-fold at 6 hr after the initiation of the Arthus reaction accompanying with a concomitant decrease in HMT activity. However, the concentrations of tryptamine and dopamine were rather decreased in the reaction site, and the net decrease of two amines was far greater than the increased amount of serotonin. The decrease in HMT activity is not stoichiometrically well elucidated from these results, and therefore, the presence of other hypothetic inhibitory factors that are increased in the Arthus reaction should be suspected.

Animals↗

PubMed1986

Relationship of CNS tryptaminergic processes and the action of LSD-like hallucinogens.

Tryptamine produces pharmacologic effects in man and the chronic spinal dog which are similar to those produced by LSD, mescaline, psilocin, DMT, DOM and DOB. These effects include tachycardia, tachypnea, mydriasis, hyperreflexia, behavioral changes and in man, hallucinations. Chronic spinal dogs treated chronically with LSD became tolerant to its ability to produce mydriasis, tachycardia, tachypnea and hyperreflexia, and were cross tolerant to the ability of tryptamine, psilocin, mescaline, DMT, DOM and DOB to produce these same effects. Further, it was found that the brain and spinal cord contained tryptamine and could release it. Further tryptamine levels were higher in the brainstem and spinal cord above the level of transection in the chronic spinal dog that in intact dogs, and the same in the spinal cord below the level of transection. These observations suggested that there were both ascending and descending tryptaminergic pathways. Supporting this hypothesis were the observations that L-tryptophan also produced hyperreflexia in the acute, but not the chronic, spinal dog and cat, and that L-tryptophan hyperreflexia was antagonized by alpha-methyldopa but not pCPA. These observations and others argue that the spinal cord and brain have tryptaminergic mechanisms which are distinct from serotoninergic mechanisms, and that LSD-like hallucinogens act in part through a tryptaminergic mechanism.

5-Hydroxytryptophan↗

PubMed1990

Monoamine oxidase activity in embryos of pike (Esox lucius).

1. Mitochondrial MAO specific activity was measured in eggs and early embryos of the teleostean fish Esox lucius using tryptamine, 5-hydroxytryptamine (5-HT) and phenylethylamine (PEA) as substrates. 2. Tryptamine is the most readily deaminated substrate in mitochondria isolated from unfertilized eggs and embryos at the stages of cleavage, blastula and gastrula. 3. Monoamine oxidase activity gradually decreases during development and at the gastrula stage it is respectively 80% (tryptamine), 70% (5-HT) and 50% (PEA) of that found in the egg using the corresponding substrate. 4. The inhibition of egg MAO activity by clorgyline and deprenyl measured in E. lucius eggs using tryptamine as substrate, indicates the presence of a single form of MAO not corresponding to the MAO A and MAO B described in terrestrial vertebrates.

Animals↗

PubMed1998

A comparison of N,N-dimethyltryptamine, harmaline, and selected congeners in rats trained with LSD as a discriminative stimulus.

1. A series of N-substituted tryptamines was compared with a series of beta-carbolines in rats trained to discriminate LSD (0.1 mg/kg) from saline. 2. Intermediate levels of substitution were elicited by MDMT (76.4%), DMT (77.9%), and DET (48.7%). 6-F-DET produced 41.3% LSD-appropriate responding at a dose of 6.0 mg/kg but only 4 of 8 subjects completed the test session thus precluding statistical analysis. Bufotenine (25.8%) also failed to substitute. Although none of the tryptamines substituted completely for LSD, the pattern of substitution is consonant with what is known of their activity in humans. MDMT, DMT, and DET are well established in the literature as hallucinogens but the same cannot be said for 6-F-DET and bufotenine. 3. Of the beta-carbolines tested, none substituted for LSD completely and only harmane elicited intermediate substitution (49.5%). No significant generalization of the LSD stimulus to 6-methoxyharmalan, harmaline, or THBC was observed. Thus, in contrast to the tryptamines, scant ability to substitute for LSD was observed in the beta-carbolines tested. 4. Taken together, the present data indicate that the representative tryptamines employed in the present study exhibit greater similarity to the LSD stimulus than do representative beta-carbolines. The receptor interactions responsible for these differences remain to be determined.

Animals↗

PubMed1993

Pharmacological profile of the 5-hydroxytryptamine receptor of Fasciola hepatica body wall muscle.

5-HT is a candidate for the excitatory transmitter at the neuromuscular junction in trematodes including Fasciola hepatica. This study has determined the response of a muscle strip preparation from Fasciola hepatica to 5-HT and a range of agonists that distinguish between the vertebrate receptor 5-HT subtypes. 5-HT increased the resting tone and the rhythmic activity of the muscle strip. Of the 19 compounds tested, only 10 had an effect similar to 5-HT and all but 2 of these were tryptamine compounds. 5-HT was more potent than tryptamine whilst 4-OH-tryptamine had no effect, suggesting that the response is mediated by a 5-HT rather than a tryptamine receptor. 5-Fluorotryptamine and 5-carboxyamidotryptamine were the most potent agonists. 8-OH-DPAT also mimicked the effect of 5-HT, though less potently. Assuming that these agents elicit their response through a common receptor, this suggests the presence of a 5-HT receptor with similar properties in terms of agonist recognition as the vertebrate 5-HT1 class of receptor involved in controlling Fasciola muscle motility.

8-Hydroxy-2-(di-n-propylamino)tetralin↗

PubMed2002

Targeting tryptophan decarboxylase to selected subcellular compartments of tobacco plants affects enzyme stability and in vivo function and leads to a lesion-mimic phenotype.

Tryptophan decarboxylase (TDC) is a cytosolic enzyme that catalyzes an early step of the terpenoid indole alkaloid biosynthetic pathway by decarboxylation of L-tryptophan to produce the protoalkaloid tryptamine. In the present study, recombinant TDC was targeted to the chloroplast, cytosol, and endoplasmic reticulum (ER) of tobacco (Nicotiana tabacum) plants to evaluate the effects of subcellular compartmentation on the accumulation of functional enzyme and its corresponding enzymatic product. TDC accumulation and in vivo function was significantly affected by the subcellular localization. Immunoblot analysis demonstrated that chloroplast-targeted TDC had improved accumulation and/or stability when compared with the cytosolic enzyme. Because ER-targeted TDC was not detectable by immunoblot analysis and tryptamine levels found in transient expression studies and in transgenic plants were low, it was concluded that the recombinant TDC was most likely unstable if ER retained. Targeting TDC to the chloroplast stroma resulted in the highest accumulation level of tryptamine so far reported in the literature for studies on heterologous TDC expression in tobacco. However, plants accumulating high levels of functional TDC in the chloroplast developed a lesion-mimic phenotype that was probably triggered by the relatively high accumulation of tryptamine in this compartment. We demonstrate that subcellular targeting may provide a useful strategy for enhancing accumulation and/or stability of enzymes involved in secondary metabolism and to divert metabolic flux toward desired end products. However, metabolic engineering of plants is a very demanding task because unexpected, and possibly unwanted, effects may be observed on plant metabolism and/or phenotype.

Aromatic-L-Amino-Acid Decarboxylases↗

PubMed1977

Effect of neuroleptics and other drugs on monoamine uptake by membranes of adrenal chromaffin granules.

1 The effects have been investigated of various reserpine-like, neuroleptic, antidepressant and other compounds on the adenosine-5'-triphosphate (ATP)-dependent uptake of noradrenaline (NA) (reserpine-sensitive) and tryptamine (reserpine-resistant) by membranes of isolated chromaffin granules of bovine adrenal medulla. 2 Reserpine and Ro 4-1284 (2-hydroxy-2-ethyl-3-isobutyl-9,10-dimethoxy-hexahydro-11bH-benzo(a)quinolizine) as well as neuroleptics (e.g. chlorpromazine and haloperidol) inhibited the NA uptake, but the reserpine-like drugs were more potent. In contrast, Ro 4-1284 showed a considerably weaker effect thatn the neuroleptics in interfering with tryptamine uptake. Chlorpromazine had about the same potency in inhibiting NA and tryptamine uptake, whereas the action of haloperidol was more pronounced on the uptake of NA than of tryptamine. 3 The relative potencies of neuroleptic drugs in inhibiting NA uptake by granule membranes in vitro corresponded only partly to their relative potencies in enhancing dopamine turnover in vivo. 4 The inhibition of NA uptake by chloropromazine and Ro 4-1284 appeared to be of the noncompetitive type. 5 Chlorpromazine did not influence the decrease in ATP induced by granule membranes in the incubation medium. 6 Other basic, but not acidic compounds also inhibited NA uptake by granule membranes; their potency was of the order of that of chlorpromazine (antidepressants) or weaker (e.g. benzodiazepines). 7 In conclusion, the mechanism of action of neuroleptics probably differs from that of reserpine-like drugs in the inhibition of monoamine uptake by membranes of catecholamine storage organelles. While interference with the granular storage of dopamine at the granule membrane level may contribute to the in vivo action of neuroleptics (e.g. in enhancing dopamine turnover), additional effects of these drugs must be involved in vivo, e.g. blockade of pre- and postsynaptic dopamine receptors.

2H-Benzo(a)quinolizin-2-ol, 2-Ethyl-1,3,4,6,7,11b-↗

PubMed1982

Rate-limiting step in the metabolism of polar and non-polar monoamines in lung and liver.

1 Uptake of the non-hydroxylated amines, [14C]-tryptamine and [14C]-benzylamine in rat lung, infused through the pulmonary circulation, was not saturable over the concentration range 2.5-1,000 microM. 2 The kinetic constants for deamination of a variety of hydroxylated and non-hydroxylated monoamines in liver, perfused via the portal circulation, with monoamine oxidase activity in homogenates of liver were similar. 3 In lung, uptake of both [14C]-tryptamine and [14C]-benzylamine was inhibited by the monoamine oxidase inhibitor deprenyl and competition occurred between tryptamine, benzylamine and beta-phenylethylamine for uptake. 4 These results indicate that tryptamine and benzylamine metabolism in lung is not limited by uptake, unlike that of the hydroxylated amines 5-hydroxytryptamine and noradrenaline and that uptake resembles that of beta-phenylethylamine in lung. 5 the selectivity of the lung in handling monoamines is not shown by the liver, suggesting that lung has a specific role in clearing certain biogenic monoamines.

Amines↗

PubMed1983

A role for an indoleamine other than 5-hydroxytryptamine in the hypothalamic thermoregulatory pathways of the rat.

1. Intrahypothalamic injection of either 5-hydroxytryptamine (5-HT) (20 mug) or tryptamine (1 mug) caused hypothermia and hyperthermia respectively in lightly restrained rats maintained at an ambient temperature of 20 +/- 1 degrees C.2. Both the 5-HT- and the tryptamine-sensitive sites were located within the same region of the preoptic area.3. When rats were tested at different ambient temperatures (4, 20 and 29 degrees C), intrahypothalamic injection of 5-HT caused a marked fall in core temperature (-1.3 degrees C) in rats maintained at 4 degrees C, but smaller responses were obtained at 20 and 29 degrees C (-0.9 and -0.5 degrees C respectively). Tryptamine caused a significant hyperthermia in rats kept at 20 degrees C, but had no significant effect in rats maintained at either 4 or 29 degrees C.4. The hypothermic effect of 5-HT was selectively antagonized by systemic pre-treatment with cyproheptadine (2.5 mg/kg), but not by methergoline (0.625 mg/kg) and methysergide (0.2 mg/kg). In contrast, the hyperthermic effect of tryptamine was blocked by methergoline and methysergide, but not by cyproheptadine.5. Cyproheptadine (2.5 mg/kg) reduced the ability of rats to cope with a heat load but had no effect on the response to cold. In contrast, methergoline (0.625 mg/kg) and methysergide (0.2 mg/kg) reduced the ability to cope with cold but the rats' ability to cope with a heat load remained intact.6. These results suggest the existence of two indoleamine pathways within the preoptic anterior hypothalamus involved in the control of body temperature: a serotonergic pathway mediating heat loss and a non-serotonergic pathway mediating heat gain. The non-serotonergic system may exert its effects by modulating the activity of a central serotonergic system.

Animals↗

PubMed2004

The effects of vasoactive amines found in the equine hindgut on digital blood flow in the normal horse.

REASONS FOR PERFORMING STUDY: Disturbances of digital blood flow are thought to be fundamental to the pathophysiology of acute laminitis. However, factors linking the initiating events in the equine hindgut with these disturbances in the foot remain to be determined. HYPOTHESIS: Amine compounds, formed by bacteria in the equine hindgut, have digital vasoconstrictor effects in vivo. METHODS: Tryptamine (1.6 microg/kg/min) and phenylethylamine (2.13 microg/kg/min) were infused i.v. into standing nonsedated horses. Digital blood flow was measured by Doppler ultrasound and foot surface temperature was monitored. Plasma 5-hydroxytryptamine (5-HT) concentrations were measured by HPLC. RESULTS: Tryptamine and phenylethylamine infusions had no effect on systemic arterial blood pressure or heart rate, but caused significant decreases in digital arterial blood flow (mean +/- s.e. 29.2 +/- 8.5 and 18.4 +/- 6.8%, respectively). Both amines also caused decreases in dorsal hoof wall temperature (0.6 +/- 0.1 and 0.5 +/- 0.1 degrees C for tryptamine and phenylethylamine, respectively) and concomitant increases in plasma 5-HT concentration. CONCLUSIONS: Tryptamine and phenylethylamine caused reduction of digital blood flow, effects which may have been mediated, in part, via displacement of 5-HT from platelets. POTENTIAL RELEVANCE: Amine compounds occurring in the equine hindgut, if released into the circulation following carbohydrate overload, could contribute to selective digital vasoconstriction. Further work in ponies and horses, with naturally occurring laminitis, is necessary to determine whether amines represent a therapeutic target in this disease.

Acute Disease↗

PubMed1977

Production of formaldehyde from N5-methyltetrahydrofolate by normal and leukemic leukocytes.

Extracts of human normal and leukemic leukocytes contain an enzyme that catalyzes a transfer of labeled methyl carbon from N5-[14C]methyltetrahydrofolate to tryptamine. Evidence is presented that this reaction is not attributable to a methyltransferase but to the following reaction sequence: (a) an oxidation of N5-[14C]methyltetrahydrofolate to N5, N10-[14C]methylenetetrahydrofolate that is catalyzed by N5, N10-methylenetetrahydrofolate reductase (EC 1.1.1.68); (b) spontaneous release of [14C]formaldehyde from N5, N10-[14C]methylenetetrahydrofolate; and (c) nonenzymatic condensation of [14C]formaldehyde with tryptamine to form a radioactive carboline derivative. The occurrence of this sequence in leukocytes is suggested by data that show that the enzyme reaction is strongly stimulated by addition of flavin adenine dinucleotide and that the final product is chromatographically identical to the adduct formed in the reaction of [14C]formaldehyde with tryptamine. In the absence of tryptamine, a product accumulates that can react with other HCHO acceptors, i.e., beta-phenylethylamine and dimedone; another reaction product is tetrahydrofolate. Production of formaldehyde is relatively more active in normal lymphocytes than in normal granulocytes, but it is even higher in lymphocytes of chronic lymphocytic leukemia. Activity in granulocytes from a subject with chronic myelocytic leukemia is also elevated but to a lesser extent than activity in lymphocytes of chronic lymphocytic leukemia. Activity in granulocytes from a subject with chronic myelocytic leukemia is also elevated but to a lesser extent than activity in lymphocytes of chronic lymphocytic leukemia. Formaldehyde production in leukocytes is only slightly stimulated by addition of various cobalamins, and activity is normal in leukocytes from a vitamin B12-deficient patient. We conclude that the system is cobalamin independent. Thus, there exists an active pathway from N5-methyltetrahydrofolate to tetrahydrofolate other than the one catalyzed by cobalamin-dependent N5-methyltetrahydrofolate-homocysteine methyltransferase.

5-Methyltetrahydrofolate-Homocysteine S-Methyltran↗

PubMedDate not supplied

[Production of non-volatile amines by strains of enterococci].

During the last few years there has been great interest concerning the problems related with the presence of pressor amines in different kinds of cheese, specially since the "cheese syndrome" was made evident. Since the capacity of the bacterial groups involved in cheese manufacture to produce these amines has not yet been clarified, it was decided to study the production capacity of tyramine, tryptamine and histamine of enterococci strains probably used in the starter cultures. Forty-one enterococci strains were analysed cultivating them in milk and in milk with the addition of the corresponding aminoacids. It was determined that only low percentages of Streptococcus faecalis subsp. liquefaciens and Streptococcus durans strains (34% and 11% respectively) produced traces of tyramine and tryptamine in milk. But when cultivated in the presence of the corresponding aminoacids, a large percentage of strains of all the species produced tyramine in high concentrations and different percentages of them produced tryptamine in concentrations no higher than 200 ppm. All strains analysed proved to be unable to produce histamine. It can be concluded that there exists a strong probability for enterococci to produce tyramine and tryptamine in different concentrations specially when developed in the presence of the corresponding aminoacids.

Amino Acids↗

PubMed1985

Atypical indolamine-immunoreactive cell groups in the dorsal myelencephalon of the rat.

The presence of atypical indolamine-immunoreactive (IAI) neurones in the dorsal myelencephalon of the rat was demonstrated by means of peroxidase-antiperoxidase (PAP) immunocytochemistry. Besides the area postrema, two other regions, viz. the solitary complex and the superficial rostral cuneate fascicle, were found to contain neuronal perikarya displaying a normally weak staining which was markedly enhanced after monoaminoxidase (MAO) inhibition. In contrast to immunoreactive cells of the periaqueductal central gray, the dorsal myelencephalic IAI neurons were undetectable after serotonin synthesis inhibition with p-chlorophenylalanine (PCPA), as were immunoreactive terminal neuropils in most brainstem areas. However, sequential treatment with the MAO inhibitor, iproniazid, completely reversed the PCPA-induced suppression of perikaryal immunoreactivity and partially restored axonal staining. None of the atypical cell groups displayed a detectable formaldehyde-induced specific histofluorescence. Since brain levels of tryptamine are likely to increase significantly after MAO inhibitor/PCPA treatment, and furthermore tryptamine can be assumed to cross-react with serotonin, it is suggested that the observed atypical IAI neurons may represent either a subpopulation of serotoninergic neurons; previously postulated true tryptamine neurons; or non-indolaminergic neurons endowed with a selective uptake mechanism for serotonin or tryptamine. These results corroborate the view that different types of indolamine neurons exist in the rat brainstem. Moreover, they underscore the need for cautious interpretation of serotonin neuron mapping studies involving the use of MAO inhibitors.

Animals↗