DMT analogues: N-ethyl-N-propyl-tryptamine and N-allyl-N-methytryptamine as their hydro-fumarate salts.

The solid-state structures of the hydro-fumarate salts of two N,N-di-alkyl-tryptamines, namely N-ethyl-N-propyl-tryptammonium (EPT) hydro-fumarate {systematic name: [2-(1H-indol-3-yl)eth-yl](meth-yl)propyl-aza-nium 3-carb-oxy-prop-2-enoate}, C(15)H(23)N(2) (+)·C(4)H(3)O(4) (-), and N-allyl-N-methyl-tryptammonium (MALT) hydro-fumarate {systematic name: [2-(1H-indol-3-yl)eth-yl](meth-yl)(prop-2-en-1-yl)aza-nium 3-carb-oxy-prop-2-enoate}, C(14)H(19)N(2) (+)·C(4)H(3)O(4) (-), are reported. Both compounds possess a protonated tryptammonium cation, and a hydro-fumarate 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.