Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine.

ABSTRACT: The title compound {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-(prop-2-en-1-yl)prop-2-en-1-amine), C₁₇H₂₂N₂O, has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules are linked by strong N-H⋯N hydrogen bonds into zigzag chains with graph-set notation C(7) along the [010] direction.

SUBMITTER: Chadeayne AR

PROVIDER: S-EPMC9462216 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine.

Chadeayne Andrew R AR Pham Duyen N K DNK Golen James A JA Manke David R DR

IUCrData 20200417 Pt 4

The title compound {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-(prop-2-en-1-yl)prop-2-en-1-amine), C17H22N2O, has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules are linked by strong N-H⋯N hydrogen bonds into zigzag chains with graph-set notation C(7) along the [010] direction. ...[more]

PMID: 36338299

Similar Datasets

5-Meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate.

Project description:The solid-state structures of the synthetic psychedelic 5-meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT) {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-amine}, C17H25N2O, and its fumarate salt, bis-(5-meth-oxy-N,N-di-n-propyl-tryptammonium) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-aminium} but-2-ene-dio-ate), 2C17H25N2O+·C4H2O4 2-, are reported. The freebase has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules are linked together by N-H⋯N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [001].

| S-EPMC8100262 | biostudies-literature

Norpsilocin: freebase and fumarate salt.

Project description:The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hy-droxy-N-methyl-tryptamine (4-HO-NMT); systematic name: 3-[2-(methyl-amino)-eth-yl]-1H-indol-4-ol}, C11H14N2O, and its fumarate salt (4-hy-droxy-N-methyl-tryptammonium fumarate; systematic name: bis-{[2-(4-hy-droxy-1H-indol-3-yl)eth-yl]methyl-aza-nium} but-2-enedioate), C11H15N2O+·0.5C4H2O4 2-, are reported. The freebase of 4-HO-NMT has a single mol-ecule in the asymmetric unit joined together by N-H⋯O and O-H⋯O hydrogen bonds in a two-dimensional network parallel to the (100) plane. The ethyl-amine arm of the tryptamine is modeled as a two-component disorder with a 0.895 (3) to 0.105 (3) occupancy ratio. The fumarate salt of 4-HO-NMT crystallizes with a tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The ions are joined together by N-H⋯O and O-H⋯O hydrogen bonds to form a three-dimensional framework, as well as π-π stacking between the six-membered rings of inversion-related indoles (symmetry operation: 2 - x, 1 - y, 2 - z).

| S-EPMC7133046 | biostudies-literature

N-Cyclohexyltryptamine: freebase, bromide and fumarate

Project description:The crystal structure of the freebase of the monoalkyl tryptamine N-cyclohexyltryptamine is presented, along with those of its bromide and fumarate salts. The solid-state structures of N-cyclohexyltryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine}, C16H22N2, and two of its salts, N-cyclohexyltryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium bromide}, C16H23N2+·Br−, and N-cyclohexyltryptammonium fumarate (III) (systematic name: bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate), 2C16H23N2+·C4H2O42−, were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N—H⋯N hydrogen bonds. The bromide salt is held together by N—H⋯Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H⋯O hydrogen bonds.

| S-EPMC10439405 | biostudies-literature

E-Liquids from Seven European Countries-Warnings Analysis and Freebase Nicotine Content.

Project description:Electronic cigarettes are available in a variety of devices with e-liquids also available in many flavors, and nicotine concentrations, albeit less than 20 mg/mL in Europe. Given the dynamics of these products, it is important to evaluate product content, including labeling, nicotine content versus labeled claim, nicotine form, and other aspects that may help policy decisions and align with the Tobacco Product Directive (TPD). Herein, we performed a study on 86 e-liquids from seven European countries (Croatia, Czech Republic, France, Germany, Italy, Poland, and the United Kingdom) with 34 different liquid brands and 57 different flavors. Nicotine content versus labeled claim, labeling, volume, pH, and nicotine form (i.e., freebase nicotine) were evaluated. From all tested products, eight of them from Germany, Poland, and UK (from 3 to 18 mg/mL), met the ±2% criteria. The ±10% criteria was fulfilled by 50 (58.1%) liquids from all countries. Among 71 liquids which contained nicotine, (one e-liquid labeled as 6 mg/mL had no nicotine level quantified), the amount of freebase nicotine differed from 0 to 97.8%, with a mean value 56.5 ± 35.7. None of the tested liquids had nicotine salt listed in the ingredients. Therefore, a low level of freebase nicotine in some liquids was most likely achieved by added flavorings. All tested liquids presented in this study met the basic requirements of the TPD. There were differences in the scope of information about harmfulness, type of warnings on packaging, attaching leaflets, placing graphic symbols, and discrepancies between the declared and quantified nicotine concentrations.

| S-EPMC8875468 | biostudies-literature

Bis(diallyl-benzimidazolium) tetra-bromidocuprate(II).

Project description:The structure of the title ionic copper(II) compound, (C(13)H(15)N(2))(2)[CuBr(4)], is built up of isolated 1,3-diallyl-benzimidazolium cations and [CuBr(4)](2-) anions which are inter-connected by electrostatic inter-actions. Differences in packing of the heterocyclic cores results in a different structure compared with earlier investigated chloride and bromide analogues.

| S-EPMC2961985 | biostudies-literature

Reductive Hydroformylation of Isosorbide Diallyl Ether.

Project description:Isosorbide and its functionalized derivatives have numerous applications as bio-sourced building blocks. In this context, the synthesis of diols from isosorbide diallyl ether by hydrohydroxymethylation reaction is of extreme interest. This hydrohydroxymethylation, which consists of carbon-carbon double bonds converting into primary alcohol functions, can be obtained by a hydroformylation reaction followed by a hydrogenation reaction. In this study, reductive hydroformylation was achieved using isosorbide diallyl ether as a substrate in a rhodium/amine catalytic system. The highest yield in bis-primary alcohols obtained was equal to 79%.

| S-EPMC8658770 | biostudies-literature

1,4-Phenyl-ene diallyl bis-(carbonate).

Project description:The title mol-ecule, C14H14O6, is based on a benzene core di-substituted by allyl carbonate groups in the para positions. The mol-ecule is placed on an inversion centre, and the substituents are twisted with respect to the central benzene ring plane. The crystal structure does not include significant inter-molecular inter-actions other than weak C-H⋯O contacts between CH groups in the benzene ring and carbonate O atoms.

| S-EPMC9993898 | biostudies-literature

A narrative synthesis of research with 5-MeO-DMT.

Project description:Background5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a naturally occurring, short-acting psychedelic tryptamine, produced by a variety of plant and animal species. Plants containing 5-MeO-DMT have been used throughout history for ritual and spiritual purposes. The aim of this article is to review the available literature about 5-MeO-DMT and inform subsequent clinical development.MethodsWe searched PubMed database for articles about 5-MeO-DMT. Search results were cross-checked against earlier reviews and reference lists were hand searched. Findings were synthesised using a narrative synthesis approach. This review covers the pharmacology, chemistry and metabolism of 5-MeO-DMT, as well epidemiological studies, and reported adverse and beneficial effects.Results5-MeO-DMT is serotonergic agonist, with highest affinity for 5-HT1A receptors. It was studied in a variety of animal models, but clinical studies with humans are lacking. Epidemiological studies indicate that, like other psychedelics, 5-MeO-DMT induces profound alterations in consciousness (including mystical experiences), with potential beneficial long-term effects on mental health and well-being.Conclusion5-MeO-DMT is a potentially useful addition to the psychedelic pharmacopoeia because of its short duration of action, relative lack of visual effects and putatively higher rates of ego-dissolution and mystical experiences. We conclude that further clinical exploration is warranted, using similar precautions as with other classic psychedelics.

| S-EPMC8902691 | biostudies-literature

1,3-Diallyl-2-methyl-benzimidazolium bromide dihydrate.

Project description:The bonds in the five-membered ring of the title hydrated salt, C(14)H(17)N(2) (+)·Br(-)·2H(2)O, are delocalized. The cation lies on a special position of m site symmetry such that the mirror plane passes through the imidazol-yl-methyl bond and is perpendicular to the plane of the cation. The anion lies on another special position of 2 site symmetry. The anion and uncoordinated water mol-ecule are linked into a chain by O-H⋯O hydrogen bonds. One of the water O atoms is disordered over two sites of equal occupancy.

| S-EPMC2970382 | biostudies-literature

Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use.

Project description:To support clinical use, a multigram-scale process has been developed to provide 5-MeO-DMT, a psychedelic natural product found in the parotid gland secretions of the toad, Incilius alvarius. Several synthetic routes were initially explored, and the selected process featured an optimized Fischer indole reaction to 5-MeO-DMT freebase in high-yield, from which the 1:1 succinate salt was produced to provide 136 g of crystalline active pharmaceutical ingredient (API) with 99.86% peak area by high-performance liquid chromatography (HPLC) and a net yield of 49%. The report provides in-process monitoring, validated analytical methods, impurity formation and removal, and solid-state characterization of the API essential for subsequent clinical development.

| S-EPMC7745443 | biostudies-literature