5-MeO-DALT: the freebase of N,N-diallyl-5-methoxytryptamine

The solid-state structure of the synthetic psychedelic 5-methoxy-N,N-diallyltryptamine (5-MeO-DMT) is reported in its freebase form.


Structure description
Psychedelics have garnered a great deal of study of late as potential therapeutics for mood disorders (Davis et al., 2020;Carhart-Harris & Goodwin, 2017). Toads in the Bufonidae family release alkaloid secretions when they experience stress. These toads are the genesis of the urban myth of 'licking toads' because the secretion contains psychedelic tryptamines. The secretion has contents that can vary greatly from species to species. It is a medley of different chemicals; the skin of the species Bufo alvarius, a desert toad of Arizona, contains a number of indolealkylamines, including bufotenine, O-methylbufotenine, and bufoviridine, among many others (Erspamer et al., 1967).
Recent studies have shown that the psychotropic experiences of inhaling dried toad excretion and that of inhaling pure synthetic O-methylbufotenine ] are markedly different (Uthaug, Lancelotta, van Oorsouw et al., 2019;Uthaug, Lancelotta, Szabo et al., 2019). The varied experiences suggests that the other tryptamines have significant activity in the psychedelic effects, or that they work in combination through an entourage effect. Accordingly, it is important to understand the pharmacology of not just 5-MeO-DMT, but all of the tryptamines in bufotoxin, and other related molecules. 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT), streetname Foxtrot, is a synthetic analog of O-methylbufotenine first synthesized by Alexander Shulgin in 2004 (Shulgin & data reports Shulgin, 2016). The compound is noted for its quick onset and rapid drop-off, when compared to other psychotropic tryptamines (Corkery et al., 2012), and can cause acute delerium and rhabdomyolysis (Kalasho & Nielsen, 2016). The pharmacology of the compound demonstrates activity at the 5-hydroxytryptamine (5-HT) receptors, particularly 5-HT 1A , 5-HT 1D , 5-HT 2B , 5-HT 6 , and 5-HT 7 , though slightly less active at the 5-HT 2A receptor, which is believed to be responsible for most psychotropic activity (Cozzi & Daley, 2016). As these molecules become more relevant in the treatment of mood disorders, it will be important to have analytically pure, wellcharacterized compounds, ideally as crystalline materials. Herein, we report the solid-state structure of 5-methoxy-N,Ndiallyltryptamine.
The asymmetric unit of 5-methoxy-N,N-diallyltryptamine contains a single tryptamine molecule (Fig. 1). The indole unit is nearly planar with a deviation from planarity of 0.015 Å . The methoxy group is in the same plane, with the indole and methoxy group showing an r.m.s. deviation of only 0.025 Å . The ethylamine group is turned significantly from the indole plane, with a C1-C8-C9-C10 torsion angle of 103.7 (2) . The molecules are held together by an N1-H1Á Á ÁN2 hydrogen bond between the indole N-H and the amino nitrogen atom. These hydrogen bonds join the molecules together along [010] ( Table 1). The crystal packing of the title compound is shown in Fig. 2.

Synthesis and crystallization
Slow evaporation of an acetone solution of a commercial sample (The Indole Shop) of 5-MeO-DALT freebase resulted in the formation of crystals of 5-methoxy-N,N-diallyltryptamine suitable for X-ray analysis.

Figure 2
The crystal packing of 5-methoxy-N,N-diallyltryptamine, viewed along the a axis. The N-HÁ Á ÁN hydrogen bonds (Table 1) are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

data-2
IUCrData (2020). 5, x200498 Refinement. Hydrogen atom H1 was found from a difference-Fourier map and refined isotropically, using a DFIX restrain with an N-H distance of 0.86 (1) Å. The isotropic displacement parameter was set to 1.2U eq of the parent indolic nitrogen atom. All other hydrogen atoms were placed in calculated positions with appropriate carbon-hydrogen bond lengths: (sp 2 ) 0.93 Å, (CH 3 ) 0.96 Å, (CH 2 ) 0.97 Å. Isotropic displacement parameters were set to 1.2U eq (C) for sp 2 and CH 2 parent carbon atoms and 1.5U eq (C-methyl)