Synthesis of psilocin labelled with <sup>14</sup>C and <sup>3</sup>H

Poon, Grace K.; Chui, Y. C.; Law, F. C. P.

doi:10.1002/jlcr.2580230207

Cited by 7 publications

(5 citation statements)

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“…The 5-HTia affinities of the 1-methyl (34) and 1-thiomethyl (36) derivatives were similar to those of most of the acyl derivatives (27)(28)(29)(30)(31) and the propyl derivative 24 and nonselective vs D2 receptors. The 1-thiomethyl derivative 36 seemed to be a moderately active agonist in vivo in both dopaminergic and serotonergic systems.…”

Section: Resultsmentioning

confidence: 69%

“…The results using principal least squares regression will be presented in a subsequent article.40 However, some interesting SAR findings can be extracted without advanced statistical methods. The fact that the formyl derivatives 5 and 21 were more potent than the other acyl analogs (23,(28)(29)(30)(31)) may be explained by torsional barriers. The s-cis conformation ( = 0°; Figure 4) of the acyl moiety is favored only for the formyl compounds, whereas torsional drivers of other less potent acyl analogs reveal that the minima are off-plane (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

“…1 -[8-(Dipropylamino) -6,7,8,9-tetrahy dro-3H-benz [e]indol-1 -yl]ethanone (28). A mixture of 6,7,8,9-tetrahydro-ALZVdipropyl-3iT-benz[e]indol-8-amine (4) (108 mg, 0.40 mmol) and phosphorus oxychloride (200 µ , 121 mg, 0.80 mmol) in dimethylacetamide (300 µ ) was stirred at 85 °C for 3 h. Sodium hydroxide (5 M, 3 mL) was cautiously added, and the resulting mixture was stirred at 85 °C for 10 min.…”

Section: Methodsmentioning

confidence: 99%

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Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

Stjernlöf¹,

Ennis²,

Lo³

et al. 1995

J. Med. Chem.

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A series of 1-, 3-, and 4-substituted analogs to the potent 5-HT1A against 8-(dipropylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-1-carbaldehyde (5) were prepared and tested in vitro at 5-HT1A, 5-HT1D alpha, 5-HT1D beta, D2, and D3 receptors and in vivo for agonist activity in the 5-HTP and DOPA accumulation assays in reserpine-pretreated rats. Some of the compounds were resolved. The substituents used in the 1-position were chosen from a principal component analysis (PCA) plot constructed from both tabulated variables and variables calculated by semiempirical methods (PM3) and molecular mechanics software (MMX). Among the analogs prepared, some, e.g., compound 21, were equipotent to compound 5 with respect to 5-HT1A effects. All compounds were more or less selective for the 5-HT1A receptor, but many of the compounds displayed higher affinities for 5-HT1D alpha than for 5-HT1D beta receptors.

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Section: Resultsmentioning

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

Stjernlöf¹,

Ennis²,

Lo³

et al. 1995

J. Med. Chem.

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“…The previous steps were similar to those previously. This procedure was improved by Poon et al in 1985 [ 49 ] ( Scheme 11 ). Poon also described one procedure applied to the synthesis of 3 H-labeled psilocin ( Scheme 12 ).…”

Section: Resultsmentioning

confidence: 99%

A Review of Synthetic Access to Therapeutic Compounds Extracted from Psilocybe

et al. 2022

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Psychedelics are used for various pathologies of the central nervous system and are currently the subject of much research, some of which relates to the compounds contained in various Psilocybe-type hallucinogenic mushrooms. It is difficult, however, to obtain and purify sufficient quantities of these compounds from fungi to carry out biological studies, hence the need to develop simple and efficient synthetic routes. We review here the various syntheses used to obtain these molecules, focusing first on the classic historical syntheses, then the use of more recent metallo-catalyzed couplings and finally the known biocatalytic methods for obtaining these molecules. Other access routes are certainly possible and should be the subject of future research given the therapeutic interest of these compounds.

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“…Chemical purity of unlabeled psilocin was >99%. 14 C-Labeled psilocin (specific activity 0.0878 Ci/mg) was synthesized chemically in our laboratory according to Poon et al [20]. Radiochemical purity of 14 C-psilocin was determined to be >98%.…”

Section: Methodsmentioning

confidence: 99%

14C-Psilocin tissue distribution in pregnant rats after intravenous administration

Law

Poon

Chui

et al. 2014

FFHD

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Background: Many species of hallucinogenic mushrooms have been found in the genusPsilocybe. The main psychoactive chemicals of Psilocybe mushrooms are psilocin and its phosphoryloxy derivative, psilocybin. In addition to its psychedelic effects, psilocybin is an effective agent to lift the mood of depressed patients with terminal cancers. Objective:To study the dispositional kinetics of 14 C-psilocin in pregnant rats after intravenous injection, to calculate tissue dose surrogates i.e., tissue 14 C concentration and area under the concentration-time curve using the experimental data, to quantify trans-placental passage of psilocin and/or its metabolites, and to identify new psilocin metabolite(s) in rat urine.Methods: A group of 15 pregnant Wistar rats weighing between 0.30-0.36 kg was used in the study. Each rat was given a single dose of 7.5 mg/kg 14 C-psilocin i.v. Three rats were randomly selected and sacrificed at 0.5, 1.0, 2.0, 4.0, and 8.0 hr post-dosing. The maternal and fetal tissues were quickly removed and the radioactivity in these tissues determined by liquid scintillation counting. In a separate study, urine samples were collected from 6 male Wistar rats after administering 15 mg/kg of unlabeled psilocin i.p. The urine samples were collected and extracted by chloroform-methanol (9:1 v/v) and analyzed using a gas chromatograph/mass spectrometer. Results:14 C-Psilocin crossed the placental barrier of pregnant rats readily after i.v.administration; maternal tissue 14 C concentrations were found to be much higher than those in fetal tissues. The areas under the curve for maternal tissues also were much higher than the fetal tissues. In general, maternal tissues could be divided into the fast eliminating organ group, which

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Synthesis of psilocin labelled with ¹⁴C and ³H

Cited by 7 publications

References 4 publications

Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

A Review of Synthetic Access to Therapeutic Compounds Extracted from Psilocybe

14C-Psilocin tissue distribution in pregnant rats after intravenous administration

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Synthesis of psilocin labelled with 14C and 3H

Cited by 7 publications

References 4 publications

Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

Structure-Activity Relationships in the 8-Amino-6,7,8,9-tetrahydro-3H-benz[e]indole Ring System. Part 1: Effects of Substituents in the Aromatic System on Serotonin and Dopamine Receptor Subtypes

A Review of Synthetic Access to Therapeutic Compounds Extracted from Psilocybe

14C-Psilocin tissue distribution in pregnant rats after intravenous administration

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Synthesis of psilocin labelled with ¹⁴C and ³H