Bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) fumarate: a new crystalline form of miprocin

Abstract

has a singly protonated tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds. These chains are a combination of R 4 2 (20) rings, and C 2 2 (15) and C 4 4 (30) parallel chains along (110). They are further consolidated by N-HÁ Á Á interactions. There are two two-component types of disorder impacting the tryptammonium fragment with a 0.753 (7):0.247 (7) occupancy ratio and one of the fumarate oxygen atoms with a 0.73 (8):0.27 (8) ratio.

Synthesis and structure of 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) and its precursors

“…N-methyltryptamine (QQQAHA: Bergin et al, 1968). There are nine other 4-hydroxytryptamines reported in the literature, the natural product psilocin (PSILIN: Petcher & Weber, 1974), 4-hydroxy-N-methyl-N-isopropyltryptamine as its fumarate (TUFQAP: Chadeayne et al, 2020a) and hydrofumarate (RONSUL: Chadeayne et al, 2019a) salts, 4-hydroxy-N,N-di-n-propyltryptamine as its chloride (WAMGEA: Sammeta et al, 2020) and fumarate (WUCGAF: Chadeayne et al, 2019b) salts, and the four quaternary tryptamines 4-hydroxy-N,N,N-trimethyltryptamine (XUXFAA: Chadeayne et al, 2020c), 4-hydroxy-N,N-dimethyl-N-ethyltryptamine, 4-hydroxy-N,N-dimethylisopropyltryptamine, and 4-hydroxy-N,Ndi-n-propyltryptamine (EDOYIJ, EDOYUV and EDOZIK: Glatfelter et al, 2022a). The reported structures most closely related to compound (2) are indole-3-yl-N-isopropylglyoxalylamide (HUNCID: Mansell et al, 2009), 4-benzyloxyindole-3-yl-N,N-diisopropylglyoxalylamide (RUHYEY: Spaeth et al, 1997) and 4-acetoxyindole-3-yl-N,N-diethylglyoxalylamide (AVUMOT: Wu et al, 2004).…”

N-Cyclohexyltryptamine: freebase, bromide and fumarate

“…norpsilocin (Chadeayne et al, 2020b), 4-acetoxy-N,N-diallyltryptamine (Pham et al, 2021a), 5-methoxy-N,N-diallyltryptamine (Pham, Sammeta et al, 2021), 5-methoxy-N,N-din-propyltryptamine (Pham et al, 2021c), 4-hydroxy-N-methyl-N-isopropyltryptamine (Chadeayne et al, 2020a), 5-methoxy-2-methyl-N,N-dimethyltryptamine (Pham et al, 2021b), 4-hydroxy-N,N-di-n-propyltryptamine (Chadeayne, Pham et al, 2019), and 4-acetoxy-N,N-dimethyltryptamine (Chadeayne et al, 2019a).…”

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

“…and norpsilocin(CCDC 1992279;Chadeayne et al, 2020b), and the synthetic psychedelic N-methyl-N-n-propyltryptamine (WOHYAW;Chadeayne et al, 2019b). The other fumarate salts of tryptamines known are norpsilocin(CCDC 1992278;Chadeayne et al, 2020b), 4-hydroxy-N-methyl-N-isopropyltryptamine(CCDC 1962339;Chadeayne et al, 2020a), 5-methoxy-2,N,N-trimethyltryptamine and psilacetin (HOCJUH;Chadeayne et al, 2019a).…”