Analysis of information sources in references of the Wikipedia article "Tryptamine" in English language version.
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(with 250 mg, intravenously) "Tryptamine was infused intravenously over a period of up to 7.5 minutes. Physical changes included an increases in blood pressure, in the amplitude of the patellar reflex, and in pupillary diameter. The subjective changes are not unlike those seen with small doses of LSD. A point-by-point comparison between the tryptamine and LSD syndromes reveals a close similarity which is consistent with the hypothesis that tryptamine and LSD have a common mode of action."
Tryptamines that are unsubstituted on the terminal amine are good substrates for oxidative deamination by MAO. Furthermore, it has been demonstrated that tryptamine and 5-methoxytryptamine cross the blood-brain barrier with great difficulty; administration of 50 mg/kg 5-methoxytryptamine to rats results in a low brain/plasma ratio when measured 15 min post-administration (242).
MARTIN and SLOAN (1970) found that intravenously infused tryptamine increased blood pressure, dilated pupils, enhanced the patellar reflex, and produced perceptual distortions. [...] Tryptamine, but not DMT, increases locomotor activity in the mouse, while both antagonize reserpine depression (V ANE et al., 1961). [...] In the rat, tryptamine causes backward locomotion, Straub tail, bradypnea and dyspnea, and clonic convulsions (TEDESCHI et al., 1959). [...] Tryptamine produces a variety of changes in the cat causing signs of sympathetic activation including mydriasis, retraction of nictitating membrane, piloerection, motor signs such as extension of limbs and convulsions and affective changes such as hissing and snarling (LAIDLAW, 1912). [...]
[Tryptamine (T): [...] Psychoactive effects: Psychoactive, short acting due to metabolism, increased blood pressure, similar to LSD
Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
Tryptamine was first synthesized by means of Fischer indole cyclization of the phenylhydrazone of 4-aminobutyraldehyde2. Later, Majima and Hoshino3 prepared it by reduction of indol-3-yl-acetonitrile which was derived from the reaction of indol-3-yl-magnesium iodide with chloroacetonitrile. These methods have been superseded by the preparative sequence involving gramine methiodide4, and by the synthesis via indol-3-yl-glyoxylamides5,6. Other methods are the lithium aluminum hydride reduction of either 3-(2-nitroethyl)-indole7 or 3-(2-nitrovinyl)-indole8. A synthesis by the reaction of indolylmagnesium bromide with ethylene imine was also reported9. However, these methods require expensive materials and numerous steps. Now we wish to report an inexpensive one-step preparation of tryptamine from L-tryptophan (1). [...] 2. A. J. Evins, J. Chem. Soc. 99, 270 (1911).
Promotion to the staff brought Ewins into more immediate collaboration in research with Laidlaw and myself. As the Bibliography again shows, he was promptly at work with Laidlaw on the isolation of a previously unknown member of the series of the proteinogenous amines—3β-aminoethyl-indole, indole-ethylamine, or tryptamine, the amine formed by the decarboxylation of tryptophane; and Ewins proceeded to produce this base also by an artificial synthesis. I have sometimes thought, during the past few years, that Laidlaw's largely forgotten description, at that early date, of its physiological actions may, at some points, have anticipated the discovery of the actions of the nearly related 5-hydroxy-tryptamine, the natural occurrence and activities of which have recently excited so rapid a growth of attention.
Tryptamine, or indole-ethylamine, has been subjected to animal experimentation by Ewins and Laidlaw (9), Guggenheim and Loffler (10), and Guggenheim (11). The methyl derivatives of tryptamine are the results of Manske's recent work (12). [...] (9) A. J. Ewins and P. P. Laidlaw, Biochem. J., 7 (1912), 18. (10) M. Guggenheim and W. Loffler, Biochem. Z., 72 (1916), 325. (11) M. Guggenheim, Die biogenin Amine, Julius Springer, Berlin, 2nd Edition, 1924, 335. (12) R. H. F. Manske, Cun. J. Research, 5 (1931), 592.
{{cite book}}: ISBN / Date incompatibility (help)In May 1949, the structure was finally determined to be 5-hydroxytryptamine (Rapport 1949). In many ways, this was the true discovery of serotonin, for now it could be truly identified and studied.
(with 250 mg, intravenously) "Tryptamine was infused intravenously over a period of up to 7.5 minutes. Physical changes included an increases in blood pressure, in the amplitude of the patellar reflex, and in pupillary diameter. The subjective changes are not unlike those seen with small doses of LSD. A point-by-point comparison between the tryptamine and LSD syndromes reveals a close similarity which is consistent with the hypothesis that tryptamine and LSD have a common mode of action."
Tryptamines that are unsubstituted on the terminal amine are good substrates for oxidative deamination by MAO. Furthermore, it has been demonstrated that tryptamine and 5-methoxytryptamine cross the blood-brain barrier with great difficulty; administration of 50 mg/kg 5-methoxytryptamine to rats results in a low brain/plasma ratio when measured 15 min post-administration (242).
[Tryptamine (T): [...] Psychoactive effects: Psychoactive, short acting due to metabolism, increased blood pressure, similar to LSD
Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
In May 1949, the structure was finally determined to be 5-hydroxytryptamine (Rapport 1949). In many ways, this was the true discovery of serotonin, for now it could be truly identified and studied.
[Tryptamine (T): [...] Psychoactive effects: Psychoactive, short acting due to metabolism, increased blood pressure, similar to LSD
{{cite book}}: ISBN / Date incompatibility (help)Tryptamines that are unsubstituted on the terminal amine are good substrates for oxidative deamination by MAO. Furthermore, it has been demonstrated that tryptamine and 5-methoxytryptamine cross the blood-brain barrier with great difficulty; administration of 50 mg/kg 5-methoxytryptamine to rats results in a low brain/plasma ratio when measured 15 min post-administration (242).
Tryptamine was first synthesized by means of Fischer indole cyclization of the phenylhydrazone of 4-aminobutyraldehyde2. Later, Majima and Hoshino3 prepared it by reduction of indol-3-yl-acetonitrile which was derived from the reaction of indol-3-yl-magnesium iodide with chloroacetonitrile. These methods have been superseded by the preparative sequence involving gramine methiodide4, and by the synthesis via indol-3-yl-glyoxylamides5,6. Other methods are the lithium aluminum hydride reduction of either 3-(2-nitroethyl)-indole7 or 3-(2-nitrovinyl)-indole8. A synthesis by the reaction of indolylmagnesium bromide with ethylene imine was also reported9. However, these methods require expensive materials and numerous steps. Now we wish to report an inexpensive one-step preparation of tryptamine from L-tryptophan (1). [...] 2. A. J. Evins, J. Chem. Soc. 99, 270 (1911).