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 2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads

2021 ◽  
Vol 77 (2) ◽  
pp. 190-194
Author(s):  
Duyen N. K. Pham ◽  
Andrew R. Chadeayne ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
State Structure ◽  
Solid State Structure ◽  
Π Interactions ◽  
Iodide Anion ◽  
Derivatives Of

The solid-state structure of the bufotenine derivative bis(5-methoxy-2,N,N-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]dimethylazanium} (2E)-but-2-enedioate), 2C14H21N2O+·C4H2O4 2−, the bufotenidine derivative 5-methoxy-2,N,N,N-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide}, C15H23N2O+·I−, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C15H23N2O+·I−·H2O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked via N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.

scholarly journals Crystal structure of the co-crystalline adduct 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD)–4-bromophenol (1/2)

2015 ◽  
Vol 71 (5) ◽  
pp. 463-465 ◽  
Author(s):  
Augusto Rivera ◽  
Juan Manuel Uribe ◽  
Jicli José Rojas ◽  
Jaime Ríos-Motta ◽  
Michael Bolte
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Rotation Axis ◽  
The Other ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Species Association ◽  
Crystalline Adduct ◽  
Aminal Cage

The structure of the 1:2 co-crystalline adduct C8H16N4·2C6H5BrO, (I), from the solid-state reaction of 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane (TATD) and 4-bromophenol, has been determined. The asymmetric unit of the title co-crystalline adduct comprises a half molecule of aminal cage polyamine plus a 4-bromophenol molecule. A twofold rotation axis generates the other half of the adduct. The primary inter-species association in the title compound is through two intermolecular O—H...N hydrogen bonds. In the crystal, the adducts are linked by weak non-conventional C—H...O and C—H...Br hydrogen bonds, giving a two-dimensional supramolecular structure parallel to thebcplane.

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].

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.

scholarly journals 6-Bromo-1H-indole-2,3-dione hemihydrate

IUCrData ◽  
2016 ◽  
Vol 1 (1) ◽  
Author(s):  
John R. Turbitt ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Mean Deviation ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Π Interactions ◽  
Compound C ◽  
Planar Molecule

The title compound, C8H4BrNO2·0.5H2O, has a single planar molecule in the asymmetric unit with the non-H atoms having a mean deviation from planarity of 0.028 Å. There is also a half of a water molecule (twofold symmetry) present in the asymmetric unit, which hydrogen bonds with the isatin molecules through O—H...O and N—H...O hydrogen bonds to form a two-dimensional framework in theabplane. There are close Br...O contacts of 2.999 (2) Å to link the layers. The nine-membered rings of the isatin molecules stack along theaaxis with parallel slipped π–π interactions [inter-centroid distances = 3.6989 (19) and 4.1227 (19) Å].

scholarly journals Crystal structure of poly[diaqua(μ-2-carboxyacetato-κ3O,O′:O′′)(2-carboxyacetato-κO)di-μ-chlorido-dicobalt(II)]

2016 ◽  
Vol 72 (1) ◽  
pp. 21-24
Author(s):  
Yasmina Bouaoud ◽  
Zouaoui Setifi ◽  
Andrii Buvailo ◽  
Vadim A. Potaskalov ◽  
Hocine Merazig ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Two Dimensional ◽  
Acid Molecule ◽  
Carbonyl Groups ◽  
Asymmetric Unit ◽  
Dinuclear Unit

The asymmetric unit of the title polymer, [Co2(C3H3O4)2Cl2(H2O)2]n, comprises one CoIIatom, one water molecule, one singly deprotonated malonic acid molecule (HMal−; systematic name 2-carboxyacetate) and one Cl−anion. The CoIIatom is octahedrally coordinated by the O atom of a water molecule, by one terminally bound carboxylate O atom of an HMal−anion and by two O atoms of a chelating HMal−anion, as well as by two Cl−anions. The Cl−anions bridge two CoIIatoms, forming a centrosymmetric Co2Cl2core. Each malonate ligand is involved in the formation of six-membered chelate rings involving one CoIIatom of the dinuclear unit and at the same time is coordinating to another CoIIatom of a neighbouring dinuclear unit in a bridging mode. The combination of chelating and bridging coordination modes leads to the formation of a two-dimensional coordination polymer extending parallel to (001). Within a layer, O—Hwater...Cl and O—Hwater...O hydrogen bonds are present. Adjacent layers are linked through O—H...O=C hydrogen bonds involving the carboxylic acid OH and carbonyl groups.

1,1′-(2,5-Dimethyl-1,4-phenylenemethylene)di-1H-imidazole dihydrate

2006 ◽  
Vol 62 (5) ◽  
pp. o1733-o1734
Author(s):  
Wen-Hua Wang ◽  
Wei Dou ◽  
Zhong-Lu You ◽  
Wei-Sheng Liu ◽  
Da-Qi Wang
Keyword(s):  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Organic Molecule ◽  
Organic Molecules ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
One Dimensional ◽  
Compound C ◽  
Chain Links

In the title compound, C16H18N4·2H2O, there is one half-molecule (organic) and one water molecule in the asymmetric unit, the organic molecule being centrosymmetric. The separation of the two terminal N atoms is 11.296 (8) Å and the dihedral angle between the benzene and imidazole rings is 85.27 (18)°; the molecule adopts a Z-shaped conformation. A one-dimensional water chain links the organic molecules, forming a two-dimensional ladder-shaped network along the b-axis direction through intermolecular O—H...O and N—H...O hydrogen bonds.

scholarly journals Crystal structure of poly[μ6-adipato-diaquadi-μ2-oxalato-didysprosium(III)]

2014 ◽  
Vol 70 (12) ◽  
pp. m399-m400
Author(s):  
Zhi-Feng Li ◽  
Yi-Chao Zhang ◽  
Xiao-Qin Hu ◽  
Chun-Xiang Wang
Keyword(s):  
Crystal Structure ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Aqua Ligand ◽  
Three Dimensions ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Dimensional Network ◽  
Trigonal Prismatic

In the title coordination polymer, [Dy2(C6H8O4)(C2O4)2(H2O)2]n, the asymmetric unit consists of one Dy3+cation, one half of an adipate anion, two halves of oxalate anions and one coordinating water molecule. The adipate and oxalate ions are located on centres of inversion. The Dy3+cation has a distorted tricapped trigonal–prismatic geometry and is coordinated by nine O atoms, four belonging to three adipate anions, four to two oxalate anions and one from an aqua ligand. The cations are bridged by adipate ligands, generating a two-dimensional network parallel to (010). This network is further extended into three dimensions by coordination of the rigid oxalate ligands and is further consolidated by O—H...O hydrogen bonds. A part of the adipate anion is disordered over two positions in a 0.75:0.25 ratio.

scholarly journals Comparison of the crystal structures of methyl 4-bromo-2-(methoxymethoxy)benzoate and 4-bromo-3-(methoxymethoxy)benzoic acid

2016 ◽  
Vol 72 (4) ◽  
pp. 477-481
Author(s):  
P. A. Suchetan ◽  
V. Suneetha ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
P. Krishna Murthy
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Side Chain ◽  
Benzoic Acids ◽  
Asymmetric Unit ◽  
Π Interactions ◽  
Independent Molecules ◽  
Compound Ii ◽  
Derivatives Of ◽  
Fully Extended Conformation

The title compounds, C10H11BrO4, (I), and C9H9BrO4, (II), are derivatives of bromo–hydroxy–benzoic acids. Compound (II) crystallizes with two independent molecules (AandB) in the asymmetric unit. In both (I) and (II), the O—CH2—O—CH3side chain is not in its fully extended conformation; the O—C—O—C torsion angle is 67.3 (3) ° in (I), and −65.8 (3) and −74.1 (3)° in moleculesAandB, respectively, in compound (II). In the crystal of (I), molecules are linked by C—H...O hydrogen bonds, formingC(5) chains along [010]. The chains are linked by short Br...O contacts [3.047 (2) Å], forming sheets parallel to thebcplane. The sheets are linkedviaC—H...π interactions, forming a three-dimensional architecture. In the crystal of (II), moleculesAandBare linked to formR22(8) dimersviatwo strong O—H...O hydrogen bonds. These dimers are linked into ...A–B...A–B...A–B... [C22(15)] chains along [011] by C—H...O hydrogen bonds. The chains are linked by slipped parallel π–π interactions [inter-centroid distances = 3.6787 (18) and 3.8431 (17) Å], leading to the formation of slabs parallel to thebcplane.

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