'Foxtrot' fumarate: a water-soluble salt of N,N-di-allyl-5-methoxytryptamine (5-MeO-DALT)
Duyen N K Pham1, Vamshikrishna Reddy Sammeta1, Andrew R Chadeayne2
1University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA.
Abstract:
The title compound, bis-(N,N-diallyl-5-meth-oxy-tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O4 2-, 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 [111].
Related Concept Videos
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Diazonium Group Substitution: –OH and –H
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...


