scholarly journals Psilacetin derivatives: fumarate salts of the methyl–ethyl, methyl–allyl and diallyl variants of the psilocin prodrug

2021 ◽  
Vol 77 (2) ◽  
pp. 101-106
Author(s):  
Duyen N. K. Pham ◽  
Andrew R. Chadeayne ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Acid Molecule ◽  
Methyl Ethyl ◽  
Ethyl Methyl ◽  
Solid State Structures ◽  
Fumarate Salt

The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acetoxy-N-ethyl-N-methyltryptammonium (4-AcO-MET) hydrofumarate {systematic name: [2-(4-acetyloxy-1H-indol-3-yl)ethyl](methyl)ethylazanium 3-carboxyprop-2-enoate}, C15H21N2O2 +·C4H3O4 −, 4-acetoxy-N-allyl-N-methyltryptammonium (4-AcO-MALT) hydrofumarate {systematic name: [2-(4-acetyloxy-1H-indol-3-yl)ethyl](methyl)prop-2-enylazanium 3-carboxyprop-2-enoate}, C16H21N2O2 +·C4H3O4 −, and 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate–fumaric acid (1/1) (systematic name: bis{[2-(4-acetyloxy-1H-indol-3-yl)ethyl]diprop-2-enylazanium} but-2-enedioate–(E)-butenedioic acid (1/1)), 2C18H23N2O2 +·C4H2O4 2−·C4H4O4, are reported. All three salts possess a protonated tryptammonium cation. The 4-AcO-MET and 4-AcO-MALT compounds are charge-balanced by 3-carboxyacrylate (hydrofumarate) anions. The 4-AcO-DALT complex crystallizes as a two-to-one tryptammonium-to-fumarate salt, which co-crystallizes with a fumaric acid molecule. Each structure is consolidated by N—H...O and O—H...O hydrogen bonds.

scholarly journals 5-Methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT): freebase and fumarate

2021 ◽  
Vol 77 (5) ◽  
pp. 522-526
Author(s):  
Duyen N. K. Pham ◽  
Andrew R. Chadeayne ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Asymmetric Unit ◽  
One Dimensional ◽  
Solid State Structures ◽  
Fumarate Salt

The solid-state structures of the synthetic psychedelic 5-methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT) {systematic name: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine}, C17H25N2O, and its fumarate salt, bis(5-methoxy-N,N-di-n-propyltryptammonium) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium} but-2-enedioate), 2C17H25N2O+·C4H2O4 2−, are reported. The freebase has a single tryptamine molecule in the asymmetric unit. The molecules 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].

scholarly journals The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin

2019 ◽  
Vol 75 (9) ◽  
pp. 1316-1320 ◽  
Author(s):  
Andrew R. Chadeayne ◽  
Duyen N. K. Pham ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Side Chain ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Ethyl Methyl ◽  
Methyl Derivatives ◽  
Solid State Structures ◽  
Derivatives Of

The solid-state structures of the salts of two substituted tryptamines, namely N-isopropyl-N-methyltryptaminium (MiPT) fumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C14H21N2 +·C4H3O4 −, and 4-hydroxy-N-isopropyl-N-methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hydroxy-1H-indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate monohydrate}, C14H21N2O+·C4H3O4 −·H2O, are reported. Both salts possess a protonated tryptammonium cation and a 3-carboxyacrylate (hydrogen fumarate) anion in the asymmetric unit; the 4-HO-MiPT structure also contains a water molecule of crystallization. Both cations feature disorder of the side chain over two orientations, in a 0.630 (3):0.370 (3) ratio for MiPT and a 0.775 (5):0.225 (5) ratio for 4-HO-MiPT. In both extended structures, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks.

scholarly journals DMT analogues: N-ethyl-N-propyltryptamine and N-allyl-N-methytryptamine as their hydrofumarate salts

2020 ◽  
Vol 76 (8) ◽  
pp. 1201-1205 ◽  
Author(s):  
Andrew R. Chadeayne ◽  
Duyen N. K. Pham ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Extended Structure ◽  
Ethyl Group ◽  
Ethyl Methyl ◽  
Two Component ◽  
Solid State Structures

The solid-state structures of the hydrofumarate salts of two N,N-dialkyltryptamines, namely N-ethyl-N-propyltryptammonium (EPT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)propylazanium 3-carboxyprop-2-enoate}, C15H23N2 +·C4H3O4 −, and N-allyl-N-methyltryptammonium (MALT) hydrofumarate {systematic name: [2-(1H-indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium 3-carboxyprop-2-enoate}, C14H19N2 +·C4H3O4 −, are reported. Both compounds possess a protonated tryptammonium cation, and a hydrofumarate anion in the asymmetric unit. The ethyl group of the EPT cation is modeled as a two-component disorder with 50% occupancy for each component. In the extended structure, N—H...O and O—H...O hydrogen bonds generate infinite two-dimensional networks parallel to the (001) plane for both compounds.

scholarly journals Crystal structure ofL-tryptophan–fumaric acid–water (1/1/1)

2015 ◽  
Vol 71 (9) ◽  
pp. o661-o662 ◽  
Author(s):  
M. Lydia Caroline ◽  
S. Kumaresan ◽  
P. G. Aravindan ◽  
M. Peer Mohamed ◽  
G. Mani
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Solvent Molecule ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Acid Molecule ◽  
Water Solvent ◽  
Compound C ◽  
Tryptophan Molecule

In the title compound, C11H12N2O2·C4H4O4·H2O, the L-tryptophan molecule crystallized as a zwitterion, together with a neutral fumaric acid molecule and a water solvent molecule. In the crystal, the three components are linked by a series of N—H...O, O—H...O and C—H...O hydrogen bonds, forming slabs lying parallel to (001). The slabs are connected by O—H...O hydrogen bonds, involving inversion-related fumaric acid groups, leading to the formation of a three-dimensional structure.

Hydrotelluration of acetylenic esters: structural characterization of stereoisomers of methyl/ethyl β-(aryltelluro)acrylates

RSC Advances ◽  
2015 ◽  
Vol 5 (72) ◽  
pp. 58246-58254 ◽  
Author(s):  
Bandana Singh ◽  
Ashok K. S. Chauhan ◽  
Ramesh C. Srivastava ◽  
Andrew Duthie ◽  
R. J. Butcher
Keyword(s):  
Solid State ◽  
Chemical Shift ◽  
Structural Characterization ◽  
Methyl Ethyl ◽  
Acetylenic Esters ◽  
Solid State Structures

Synthesis of tellurated acrylates, ArTeCHCHCOOR and their solid state structures have been explored. The 125Te chemical shift and 2J(1H–125Te) are useful indicators of their geometry in solution.

Hydrogen Bonding of two l-(φ-Ammonioalkyl)-2-acyl-cyclopentadienides in the Solid State

2000 ◽  
Vol 55 (6) ◽  
pp. 541-545 ◽  
Author(s):  
Andreas Müller ◽  
Gerhard Maas
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Two Dimensional ◽  
Intermolecular Hydrogen Bonds ◽  
Dimensional Network ◽  
Solid State Structures ◽  
Centrosymmetric Dimers

The solid-state structures of a l-(φ-ammoniopropyl)-2-(2-thienylcarbonyl)-cyclopentadienide (2) and a l-(φ-ammoniopentyl)-2-(4-methoxybenzoyl)-cyclopentadienide (3) have been determined. Both betaines self-assemble by NH ··· O hydrogen bonds, but the motifs are different. In the ammoniopropyl case, both intramolecular and intermolecular hydrogen bonds of this type exist, the latter bond being responsible for the formation of infinite chains. In the ammoniopentyl case, intermolecular hydrogen bonds build up a two-dimensional network which contains centrosymmetric dimers held together by NH ··· O=C-aryl hydrogen bonds.

A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

1997 ◽  
Vol 50 (5) ◽  
pp. 439 ◽  
Author(s):  
Darren G. Hamilton ◽  
Daniel E. Lynch ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Neutral Donor ◽  
Hydrogen Bonding Interactions ◽  
Donor And Acceptor ◽  
Structural Preferences ◽  
Donor Acceptor ◽  
Covalently Linked ◽  
Solid State Structures

Pyromellitic diimide forms orange-coloured cocrystals of 1 : 1 stoichiometry with dialkoxynaphthalene derivatives. The solid-state structures of two examples are presented. The cocrystal formed with 2,6-dimethoxynaphthalene presents vertical stacks of alternating π-rich and π-deficient subunits with the long axes of the respective components approximately parallel. Investigation of the packing in the cocrystal also reveals a stabilizing array of hydrogen bonds between the components of adjacent stacks. Cocrystallization with 1,5-[2-(2-hydroxyethoxy)ethoxy]naphthalene, a derivative bearing hydroxy terminated ethyleneoxy chains, gives rise to an altered structural arrangement. Alternating donor- acceptor stacks once again dominate the structure but adopt a geometry where the long axes of the constituents are essentially perpendicular. Hydrogen-bonding interactions result in the formation of continuous non-covalently linked columns of donor and acceptor subunits by linking the terminal hydroxy functions of the naphthalene component to the imide protons. The structural preferences revealed by these solid-state analyses indicate that these complexes are useful prototypes of more complex neutral supramolecular assemblies.

scholarly journals Bis(N,N′,N′′-triisopropylguanidinium) fumarate–fumaric acid (1/1)

2012 ◽  
Vol 68 (6) ◽  
pp. o1906-o1906 ◽  
Author(s):  
Farouq F. Said ◽  
Basem F. Ali ◽  
Darrin Richeson ◽  
Ilia Korobkov
Keyword(s):  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Carboxyl Groups ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Compound C ◽  
Carboxylate Groups ◽  
Dimensional Network

The asymmetric unit of the title compound, C10H24N3 +·0.5C4H2O4 2−·0.5C4H4O4, comprises a triisopropylguanidinium cation, half of a fumarate dianion and half of a fumaric acid molecule; both the fumarate dianion and the fumaric acid molecule are located on inversion centres. In the crystal, intermolecular O—H...O hydrogen bonds between the carboxyl groups of the fumaric acid molecules and the carboxylate groups of the fumarate anions lead to the formation of a hydrogen-bonded supramolecular twisted chain along the b axis. The triisopropylguanidinium cations interact with the fumarate–fumaric acid chains via extensive N—H...O and C—H...O hydrogen bonds, leading to a ladder arrangement, with the cation being the rungs that bridge three curled chains of fumarate–fumaric acid. The crystal packing is stabilized by N—H...O and C—H...O (cation...fumarate/fumaric) and O—H...O (fumarate...fumaric) hydrogen bonds, consolidating a three-dimensional network.

scholarly journals 2-Phenyl-1H-imidazol-3-ium hydrogen fumarate–fumaric acid (2/1)

2012 ◽  
Vol 68 (4) ◽  
pp. o1021-o1021
Author(s):  
Hong Guo ◽  
Xin Zhang ◽  
Jian-Xia Li
Keyword(s):  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Title Compound ◽  
Inversion Center ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Compound C

The asymmetric unit of the title compound, C9H9N2+·C4H3O4−·0.5C4H4O4, consists of one 2-phenylimidazolium cation, one hydrogen fumarate anion and half a fumaric acid molecule, which lies on an inversion center. N—H...O and O—H...O hydrogen bonds connect the cations, anions and fumaric acid molecules into sheets parallel to the (102) plane.

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