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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 10| Part 6| June 2025| x250564
https://doi.org/10.1107/S2414314625005644

4-Hy­dr­oxy-N,N-diiso­propyl­tryptammonium hydro­fumarate

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Marilyn Naeem,a Andrew R. Chadeayne,b James A. Golena and David R. Mankea*

aUniversity of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and bCaaMTech, Inc., 58 Sunset Way, Suite 209, Issaquah, WA 98027, USA
*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 20 June 2025; accepted 23 June 2025; online 27 June 2025)

The solid-state structure of the title salt, C16H25N2O+·C4H3O4− {systematic name: [2-(4-hy­droxy-1H-indol-3-yl)eth­yl]bis­(propan-2-yl)aza­nium (2E)-3-carb­oxy­prop-2-enoate}, is reported. In the extended structure, the hydro­fumarate anions form linear chains propagating in the [100] direction through O—H⋯O hydrogen bonds that combine with the tryptammonium cations to generate a three-dimensional network linked by O—H⋯O and N—H⋯O hydrogen bonds.

CCDC reference: 2466286

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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

4-Hy­droxy-N,N-diiso­propyl­tryptamine (4-HO-DiPT, C16H24N2O) is a synthetic structural analog of serotonin (5-hy­droxy­tryptamine), which differs by moving the hy­droxy moiety from the 5- to the 4- position of the indole unit, and di-alkyl­ating its primary amine with two isopropyl groups. Serotonin analogs have been the subject of fascination for millenia because they alter human perception and consciousness when ingested (George et al., 2022[George, D. R., Hanson, R., Wilkinson, D. & Garcia-Romeu, A. (2022). Cult. Med. Psychiatry 46, 890-903.]), effects now attributed to the 5-HT2 A receptor (Halberstadt & Geyer, 2011[Halberstadt, A. L. & Geyer, M. A. (2011). Neuropharmacology 61, 364-381.]). Psilocybin (4-phosphor­yloxy-N,N-di­methyl­tryptamine) and psilocin (4-hy­droxy-N,N-di­methyl­tryptamine) are widely known examples, both natural products found in at least 200 species of so-called ‘magic' mushrooms (Nichols, 2020[Nichols, D. E. (2020). J. Antibiot. 73, 679-686.]). Other naturally occurring serotonin analogs (e.g. 5-MeO-DMT, DMT, bufotenine) have been identified in plants and animals (Araújo et al., 2015[Araújo, A. M., Carvalho, F., Bastos, M. L., Guedes de Pinho, P. & Carvalho, M. (2015). Arch. Toxicol. 89, 1151-1173.]). Different structural analogs of serotonin produce varied perceptual and biological effects in humans.

Recently, several studies have indicated that 5-HT2 A agonists hold tremendous potential to treat the most harmful and intra­ctable mental health conditions including depression, anxiety and post-traumatic stress disorder (PTSD). Psilocybin and other psilocin prodrugs are currently being developed as a treatment for treatment-resistant depression (TRD), anorexia and PTSD (Goodwin et al., 2022[Goodwin, G. M., Aaronson, S. T., Alvarez, O., Arden, P. C., Baker, A., Bennett, J. C., Bird, C., Blom, R. E., Brennan, C., Brusch, D., Burke, L., Campbell-Coker, K., Carhart-Harris, R., Cattell, J., Daniel, A., DeBattista, C., Dunlop, B. W., Eisen, K., Feifel, D., Forbes, M., Haumann, H. M., Hellerstein, D. J., Hoppe, A. I., Husain, M. I., Jelen, L. A., Kamphuis, J., Kawasaki, J., Kelly, J. R., Key, R. E., Kishon, R., Knatz Peck, S., Knight, G., Koolen, M. H. B., Lean, M., Licht, R. W., Maples-Keller, J. L., Mars, J., Marwood, L., McElhiney, M. C., Miller, T. L., Mirow, A., Mistry, S., Mletzko-Crowe, T., Modlin, L. N., Nielsen, R. E., Nielson, E. M., Offerhaus, S. R., O'Keane, V., Páleníček, T., Printz, D., Rademaker, M. C., van Reemst, A., Reinholdt, F., Repantis, D., Rucker, J., Rudow, S., Ruffell, S., Rush, A. J., Schoevers, R. A., Seynaeve, M., Shao, S., Soares, J. C., Somers, M., Stansfield, S. C., Sterling, D., Strockis, A., Tsai, J., Visser, L., Wahba, M., Williams, S., Young, A. H., Ywema, P., Zisook, S. & Malievskaia, E. (2022). N. Engl. J. Med. 387, 1637-1648.]). 5-Meth­oxy-N,N-di­methyl­tryptamine (5-MeO-DMT) is also in Phase 2 trials as treatment for TRD (Reckweg et al., 2023[Reckweg, J. T., van Leeuwen, C. J., Henquet, C., van Amelsvoort, T., Theunissen, E. L., Mason, N. L., Paci, R., Terwey, T. H. & Ramaekers, J. G. (2023). Front. Psychiatr. 14, 1133414.]). A prodrug of the title compound is in Phase 2 clinical trials for the treatment of post partem depression and adjustment disorder (NIH, 2025[NIH (2025). National Library of Medicine, https://clinicaltrials. gov/study/NCT06342310.]).

Alongside these clinical studies, others have sought to elucidate a structure–activity relationship (SAR), by understanding how the structural differences across serotonin analogs correlate with their pharmacoogical and, ultimately, clinical differences in human subjects. 4-Hy­droxy-N,N-diiso­propyl­tryptamine (4-HO-DiPT) was first synthesized in 1977 as its hydro­chloride salt (Repke et al., 1977[Repke, D. B., Ferguson, W. J. & Bates, D. K. (1977). J. Heterocycl. Chem. 14, 71-74.]). This sterically bulky analogue of psilocin is more selective toward serotonin receptors, binding to three of the possible 14 receptors, while psilocin and less bulky analogues often bind to ten (Glatfelter et al., 2023[Glatfelter, G. C., Naeem, M., Pham, D. N. K., Golen, J. A., Chadeayne, A. R., Manke, D. R. & Baumann, M. H. (2023). ACS Pharmacol. Transl. Sci. 6, 567-577.]). This synthetic variant of psilocin has been noted for its fast onset, brevity and intensity of action (Shulgin & Shulgin, 2016[Shulgin, A. T. & Shulgin, A. (2016). TiKHAL: The Continuation. Berkeley, CA: Transform Press.]).

In 2022, the US Drug Enforcement Agency proposed reclassifying 4-HO-DiPT to Schedule I of the Controlled Substance Act; the proposal was withdrawn due to strong public response (US DEA, January 14 and July 6, 2022a[US DEA (2022a). US Drug Enforcement Agency, January 14, 2022. https://www.federalregister.gov/documents/2022/01/14/2022-00713/schedules-of-controlled-substances-placement-of-4-hydroxy-nn-diisopropyltryptamine-4-oh-dipt (accessed January 24, 2025).],b[US DEA (2022b). US Drug Enforcement Agency, July 6, 2022. https://www.federalregister.gov/documents/2022/07/06/2022-14372/schedules-of-controlled-substances-placement-of-4-hydroxy-nn-diisopropyltryptamine-4-oh-dipt (accessed January 24, 2025).]). Alongside this proposed rescheduling of 4-HO-DiPT, Reunion Neuroscience (Toronto, Canada) initiated clinical trials of a ‘hemi-ester' prodrug of the same, i.e. 4-glutarato-N,N-diiso­propyl­tryptamine. We have published ethanol and methanol solvates of this prodrug, which are the first two crystal structures of this compound, and also the first structures of any N,N-diiso­propyl­tryptamine (Naeem et al., 2022[Naeem, M., Bauer, B. E., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2022). Acta Cryst. E78, 1034-1038.]). The propensity of this prodrug to form solvates in the solid state could potentially explain the difficulties removing impurities described in the later report on the synthesis and activity of this compound (Bryson et al., 2024[Bryson, N., Alexander, R., Asnis-Alibozek, A. & Ehlers, M. D. (2024). ACS Chem. Neurosci. 15, 2386-2395.]). While we have reported the first crystal structures of these prodrugs, the structure of the active metabolite has been absent. Herein, we report the first crystal structure of 4-hy­droxy-N,N-diiso­propyl­tryptamine as its hydro­fumarate salt.

The mol­ecular structure of the title compound is shown in Fig. 1[link]. The asymmetric unit contains one 4-hy­droxy-N,N-diiso­propyl­tryptammonium (C16H25N2O+) cation and one hydro­fumarate (C4H3O4−) anion. The indole ring of the cation is near planar with a r.m.s. deviation from planarity of 0.005 Å for the non-hydrogen atoms. The hydro­fumarate anion is slightly less planar with a r.m.s. deviation from planarity of 0.081 Å for the non-hydrogen atoms. The ethyl­amino arm of the tryptamine is turned away from the indole plane with a C7—C8—C9—C10 torsion angle of 75.9 (3)° and the C8—C9—C10—N2 grouping has an anti conformation [torsion angle = 170.4 (2)°]. One of the isopropyl groups (C11–C13) is disordered over two orientations in a 0.51 (4):0.49 (4) ratio. In the extended structure, the hydro­fumarate anions form linear chains along [100] through O—H⋯O hydrogen bonds (Table 1[link], Fig. 2[link]). These chains are connected into a three-dimensional network by O—H⋯O and N—H⋯O hydrogen bonds with the tryptammonium cations.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O4i 0.91 (1) 1.54 (2) 2.441 (3) 173 (6)
N1—H1A⋯O5ii 0.87 (1) 2.13 (2) 2.989 (3) 170 (4)
N2—H2⋯O3 0.90 (1) 1.88 (1) 2.756 (3) 165 (2)
O1—H1⋯O5iii 0.89 (1) 1.89 (1) 2.784 (3) 177 (4)
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing the atomic labeling. Displacement ellipsoids are drawn at the 50% probability level. Dashed bonds indicate a disordered component in the structure. Hydrogen bonds are shown as dashed lines.
[Figure 2]
Figure 2
The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity. Only one component of the disordered isopropyl groups are shown.

In addition to the structure reported here, there are eight other hydro­fumarate salts of tryptamines reported including those of N-ethyl-N-n-propyl­tryptamine (Cambridge Structural Database refcode GUPBOL; Chadeayne et al., 2020c[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2020c). Acta Cryst. E76, 1201-1205.]) and N-allyl-N-methyl­tryptamine (GUPBUR: Chadeayne et al., 2020c[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2020c). Acta Cryst. E76, 1201-1205.]), 4-acet­oxy-N,N-di­methyl­tryptamine (HOCJUH; Chadeayne et al., 2019a[Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2019a). Psychedelic Science Review https://psychedelicreview. com/the-crystal-structure-of-4-aco-dmt-fumarate/.]), 4-acet­oxy-N-ethyl-N-methyl­tryptamine (OJIQIK; Pham et al., 2021a[Pham, D. N. K., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021a). Acta Cryst. E77, 101-106.]) and 4-acet­oxy-N-allyl-N-methyl­tryptamine (OJIQUQ; Pham et al., 2021a[Pham, D. N. K., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021a). Acta Cryst. E77, 101-106.]), N-methyl-N-iso­propyl­tryptamine (RONSOF; Chadeayne et al., 2019c[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2019c). Acta Cryst. E75, 1316-1320.]) and 4-hy­droxy-N-methyl-N-iso­propyl­tryptamine (RONSUL; Chadeayne et al., 2019c[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2019c). Acta Cryst. E75, 1316-1320.]), and 4-propion­oxy-N,N-di­methyl­tryptamine (Glatfelter et al., 2023[Glatfelter, G. C., Naeem, M., Pham, D. N. K., Golen, J. A., Chadeayne, A. R., Manke, D. R. & Baumann, M. H. (2023). ACS Pharmacol. Transl. Sci. 6, 567-577.]). The other tryptamine structures reported with fumaric acid based counter-ions are nine (2:1) tryptamine:fumarate salts including those of the anti-cancer drug panobinostat (MIMMAA: Kenguva et al., 2023[Kenguva, G., Giri, L., Rout, S. R., Acharya, A. N. & Dandela, R. (2023). J. Mol. Struct. 1292, 136086.]), the mushroom natural product norpsilocin (MULXEZ: Chadeayne et al., 2020b[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2020b). Acta Cryst. E76, 589-593.]), 5-meth­oxy-N,N-di­allyl­tryptamine (OPUDEL: Pham et al., 2021c[Pham, D. N. K., Sammeta, V. R., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021c). Acta Cryst. E77, 416-419.]), 5-meth­oxy-N,N-di-n-propyl­tryptamine (OQIGON: Pham et al., 2021d[Pham, D. N. K., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021d). Acta Cryst. E77, 522-526.]), 4-hyd­oxy-N-methyl-N-iso­propyl­tryptamine (TUFQAP: Chadeayne et al., 2020a[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2020a). Acta Cryst. E76, 514-517.]), 5-meth­oxy-2-methyl-N,N-di­methyl­tryptamine (ULUTED: Pham et al., 2021b[Pham, D. N. K., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021b). Acta Cryst. E77, 190-194.]), 4-hy­droxy-N,N-di-n-propyl­tryptamine (WUCGAF: Chadeayne et al., 2019d[Chadeayne, A. R., Pham, D. N. K., Golen, J. A. & Manke, D. R. (2019d). IUCrData 4, x191469.]), psilacetin (XOFDOO: Chadeayne et al., 2019b[Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2019b). Acta Cryst. E75, 900-902.]), N-cyclo­hexyl­tryptamine (YITWIL: Naeem et al., 2023[Naeem, M., Le, A. N., Bauer, B. E., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2023). Acta Cryst. E79, 752-756.]), and two (2:1:1) tryptamine:fumarate:fumaric acid complexes, being those of 4-acet­oxy-N-ethyl-N-n-propyl­tryptamine (BIYKED: Pham et al., 2023[Pham, D. N. K., Sackett, N. B., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2023). IUCrData 8, x230779.]) and 4-acet­oxy-N,N-di­allyl­tryptamine (OJIQUW: Pham et al., 2021a[Pham, D. N. K., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2021a). Acta Cryst. E77, 101-106.]). There are also two structures of the 4-HO-DiPT prodrug 4-glutarato-N,N-diiso­propyl­tryptamine reported (TEKWOZ, TEKWUF: Naeem et al., 2022[Naeem, M., Bauer, B. E., Chadeayne, A. R., Golen, J. A. & Manke, D. R. (2022). Acta Cryst. E78, 1034-1038.]).

Synthesis and crystallization

Slow evaporation of a methanol/water solution of a commercial sample of ‘4-HO-DiPT fumarate' (Chem Logix) resulted in the formation of colorless blocks of the title compound suitable for X-ray analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The C11–C13 isopropyl group is disordered over two orientations in a 0.51 (4):0.49 (4) ratio. The disorder model was restrained with N—C distances of 1.50 (1) Å, as well as SADI C—C distance restraints, DELU rigid body restraints, and ISOR isotropic restraints. The structure was refined as an inversion twin.

Table 2
Experimental details

Crystal data
Chemical formula C16H25N2O+·C4H3O4−
Mr 376.44
Crystal system, space group Orthorhombic, P212121
Temperature (K) 300
a, b, c (Å) 7.9541 (3), 12.5763 (5), 20.3351 (6)
V (Å3) 2034.18 (13)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.38 × 0.24 × 0.12
 
Data collection
Diffractometer Bruker D8 Venture CMOS
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.714, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 23480, 3864, 3485
Rint 0.034
(sin θ/λ)max (Å−1) 0.611
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.095, 1.08
No. of reflections 3864
No. of parameters 295
No. of restraints 54
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.14, −0.12
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.6 (15)
Computer programs: APEX3 and SAINT (Bruker, 2018[Bruker (2018). APEX3 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 2466286

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625005644/hb4526sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625005644/hb4526Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625005644/hb4526Isup3.cml

checkCIF report


Computing details top

[2-(4-Hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium (2E)-3-carboxyprop-2-enoate top
Crystal data top
C16H25N2O+·C4H3O4−Dx = 1.229 Mg m−3
Mr = 376.44Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9289 reflections
a = 7.9541 (3) Åθ = 2.8–25.6°
b = 12.5763 (5) ŵ = 0.09 mm−1
c = 20.3351 (6) ÅT = 300 K
V = 2034.18 (13) Å3Block, colourless
Z = 40.38 × 0.24 × 0.12 mm
F(000) = 808
Data collection top
Bruker D8 Venture CMOS
diffractometer		3485 reflections with I > 2σ(I)
φ and ω scansRint = 0.034
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		θmax = 25.7°, θmin = 2.6°
Tmin = 0.714, Tmax = 0.745h = −9→9
23480 measured reflectionsk = −15→15
3864 independent reflectionsl = −18→24
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3705P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.001
S = 1.08Δρmax = 0.14 e Å−3
3864 reflectionsΔρmin = −0.12 e Å−3
295 parametersAbsolute structure: Refined as an inversion twin
54 restraintsAbsolute structure parameter: 0.6 (15)
Primary atom site location: dual
Special details top

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.

Refinement. Atoms H1, H1A, H2, and H2A were found from difference-Fourier maps and allowed to refine with restrained an N—H distance of 0.87 (1) Å and 1.20 Ueq of the parent indole nitrogen, an N—H distance 0.90 (1) Å and 1.20 Ueq of the parent ammonium nitrogen, and O—H distances of 0.90 (1) Å and 1.50 Ueq of parent oxygen atoms. All other hydrogen atoms were placed in calculated positions with appropriate riding parameters. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.7205 (3)0.45612 (17)0.21046 (10)0.0586 (5)
O20.3240 (2)0.6148 (2)0.54461 (13)0.0875 (9)
H2A0.427 (3)0.602 (4)0.527 (3)0.16 (2)*
O30.2145 (2)0.5076 (2)0.47141 (12)0.0839 (8)
O4−0.3942 (2)0.5705 (2)0.50563 (10)0.0791 (8)
O5−0.2902 (2)0.65068 (16)0.59369 (8)0.0486 (4)
N10.9479 (3)0.7045 (2)0.35061 (13)0.0586 (7)
N20.3986 (3)0.39208 (16)0.38155 (10)0.0406 (5)
C10.7910 (4)0.6762 (2)0.37158 (14)0.0531 (7)
H1B0.7381170.7034610.4087110.064*
C20.9858 (3)0.6496 (2)0.29497 (14)0.0518 (7)
C31.1308 (4)0.6528 (3)0.25608 (19)0.0673 (9)
H31.2214460.6963200.2666110.081*
C41.1325 (4)0.5891 (3)0.2022 (2)0.0764 (10)
H41.2273060.5890940.1754230.092*
C50.9968 (4)0.5233 (3)0.18541 (17)0.0689 (9)
H51.0031590.4815060.1477730.083*
C60.8555 (4)0.5198 (2)0.22348 (15)0.0514 (7)
C70.8470 (3)0.58421 (19)0.28019 (13)0.0435 (6)
C80.7230 (3)0.60230 (19)0.33038 (12)0.0440 (6)
C90.5517 (3)0.5530 (2)0.33740 (13)0.0440 (6)
H9A0.4955220.5530650.2950760.053*
H9B0.4848180.5950140.3676760.053*
C100.5650 (3)0.4400 (2)0.36269 (12)0.0411 (5)
H10A0.6163470.3961220.3289760.049*
H10B0.6385430.4391320.4007470.049*
C110.427 (2)0.2918 (10)0.4237 (8)0.052 (3)0.49 (4)
H110.3185180.2559120.4284180.062*0.49 (4)
C120.547 (3)0.2139 (15)0.3918 (12)0.101 (5)0.49 (4)
H12A0.5334340.1451210.4114930.151*0.49 (4)
H12B0.6604930.2378620.3979480.151*0.49 (4)
H12C0.5229640.2094680.3455940.151*0.49 (4)
C130.488 (3)0.320 (2)0.4921 (8)0.092 (5)0.49 (4)
H13A0.4046510.3628250.5136840.138*0.49 (4)
H13B0.5912730.3588730.4890150.138*0.49 (4)
H13C0.5057850.2559560.5168310.138*0.49 (4)
C11A0.402 (2)0.2809 (8)0.4102 (8)0.054 (3)0.51 (4)
H11A0.2845950.2599970.4178140.065*0.51 (4)
C12A0.479 (3)0.1967 (11)0.3682 (11)0.096 (5)0.51 (4)
H12D0.4934400.1329170.3935310.144*0.51 (4)
H12E0.5866970.2206070.3526480.144*0.51 (4)
H12F0.4072060.1823720.3313220.144*0.51 (4)
C13A0.484 (3)0.2892 (16)0.4766 (11)0.091 (4)0.51 (4)
H13D0.4742290.2225980.4993370.137*0.51 (4)
H13E0.4306000.3440920.5018140.137*0.51 (4)
H13F0.6012230.3062910.4711140.137*0.51 (4)
C140.2691 (4)0.3954 (2)0.32555 (13)0.0512 (7)
H140.2505910.4707410.3156890.061*
C150.3301 (5)0.3449 (3)0.26212 (17)0.0861 (12)
H15A0.4364770.3751990.2500510.129*
H15B0.2497180.3579980.2278350.129*
H15C0.3425550.2696780.2683440.129*
C160.1007 (4)0.3515 (3)0.34731 (17)0.0685 (8)
H16A0.0690790.3834920.3883580.103*
H16B0.1090150.2758780.3527250.103*
H16C0.0172800.3674230.3146430.103*
C170.2024 (3)0.5696 (3)0.51642 (13)0.0529 (7)
C180.0350 (3)0.5989 (2)0.54360 (14)0.0507 (7)
H180.0309720.6405400.5813600.061*
C19−0.1049 (3)0.5692 (2)0.51722 (12)0.0454 (6)
H19−0.0995460.5254150.4804250.055*
C20−0.2747 (3)0.6005 (2)0.54185 (12)0.0437 (6)
H1A1.015 (4)0.749 (2)0.3704 (16)0.093 (13)*
H20.355 (3)0.4362 (17)0.4119 (10)0.040 (7)*
H10.739 (5)0.423 (3)0.1724 (11)0.082 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0515 (11)0.0691 (13)0.0553 (11)−0.0176 (10)0.0101 (9)−0.0149 (10)
O20.0232 (10)0.141 (2)0.0983 (18)−0.0018 (12)0.0063 (10)−0.0682 (17)
O30.0291 (10)0.131 (2)0.0915 (16)0.0101 (11)0.0009 (10)−0.0680 (16)
O40.0235 (9)0.152 (2)0.0618 (12)0.0044 (12)0.0002 (8)−0.0417 (14)
O50.0306 (9)0.0669 (11)0.0482 (10)0.0073 (9)0.0045 (8)−0.0080 (9)
N10.0605 (16)0.0487 (13)0.0666 (16)−0.0138 (12)−0.0207 (13)0.0029 (12)
N20.0406 (11)0.0381 (10)0.0430 (10)0.0058 (9)0.0081 (9)−0.0021 (9)
C10.0628 (18)0.0453 (14)0.0510 (15)−0.0064 (14)−0.0091 (14)0.0023 (11)
C20.0486 (16)0.0426 (14)0.0641 (17)−0.0055 (12)−0.0159 (13)0.0105 (13)
C30.0415 (17)0.0646 (19)0.096 (3)−0.0155 (15)−0.0073 (16)0.0174 (19)
C40.054 (2)0.077 (2)0.098 (3)−0.0126 (17)0.0181 (18)0.006 (2)
C50.060 (2)0.073 (2)0.073 (2)−0.0121 (16)0.0139 (16)−0.0047 (17)
C60.0463 (16)0.0497 (15)0.0580 (16)−0.0083 (12)−0.0004 (12)0.0037 (13)
C70.0413 (14)0.0375 (13)0.0517 (14)−0.0033 (10)−0.0075 (11)0.0075 (11)
C80.0467 (14)0.0356 (12)0.0498 (13)−0.0013 (11)−0.0074 (11)0.0039 (10)
C90.0431 (14)0.0412 (13)0.0478 (13)0.0012 (11)−0.0017 (11)−0.0015 (11)
C100.0356 (13)0.0432 (12)0.0447 (12)0.0030 (11)0.0053 (10)−0.0013 (11)
C110.048 (5)0.049 (4)0.058 (5)−0.003 (3)0.002 (4)0.019 (4)
C120.129 (10)0.059 (6)0.114 (9)0.032 (7)0.013 (7)0.012 (5)
C130.115 (9)0.098 (10)0.062 (6)0.019 (8)−0.018 (5)0.033 (5)
C11A0.045 (5)0.053 (4)0.064 (5)−0.001 (3)0.002 (4)0.010 (3)
C12A0.126 (10)0.044 (5)0.117 (8)0.028 (6)0.018 (7)0.006 (5)
C13A0.111 (8)0.072 (7)0.091 (8)−0.002 (6)−0.025 (7)0.025 (6)
C140.0531 (16)0.0514 (14)0.0490 (14)−0.0098 (13)−0.0036 (12)−0.0052 (12)
C150.087 (3)0.107 (3)0.063 (2)−0.029 (2)0.0059 (18)−0.033 (2)
C160.0541 (17)0.077 (2)0.074 (2)−0.0149 (17)−0.0052 (16)0.0004 (17)
C170.0242 (12)0.0787 (19)0.0558 (15)0.0062 (13)0.0005 (11)−0.0235 (15)
C180.0270 (12)0.0701 (18)0.0550 (14)0.0015 (12)0.0032 (11)−0.0246 (14)
C190.0284 (12)0.0645 (17)0.0434 (12)0.0076 (12)0.0016 (10)−0.0127 (12)
C200.0258 (11)0.0672 (16)0.0382 (12)0.0038 (11)0.0038 (10)−0.0017 (12)
Geometric parameters (Å, º) top
O1—C61.365 (3)C11—H110.9800
O1—H10.891 (13)C11—C121.512 (9)
O2—H2A0.908 (14)C11—C131.512 (9)
O2—C171.260 (3)C12—H12A0.9600
O3—C171.206 (3)C12—H12B0.9600
O4—C201.260 (3)C12—H12C0.9600
O5—C201.235 (3)C13—H13A0.9600
N1—C11.366 (4)C13—H13B0.9600
N1—C21.359 (4)C13—H13C0.9600
N1—H1A0.870 (13)C11A—H11A0.9800
N2—C101.504 (3)C11A—C12A1.494 (9)
N2—C111.543 (9)C11A—C13A1.506 (9)
N2—C11A1.515 (10)C12A—H12D0.9600
N2—C141.536 (3)C12A—H12E0.9600
N2—H20.899 (13)C12A—H12F0.9600
C1—H1B0.9300C13A—H13D0.9600
C1—C81.363 (4)C13A—H13E0.9600
C2—C31.400 (4)C13A—H13F0.9600
C2—C71.409 (4)C14—H140.9800
C3—H30.9300C14—C151.517 (4)
C3—C41.357 (5)C14—C161.515 (4)
C4—H40.9300C15—H15A0.9600
C4—C51.402 (5)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C5—C61.366 (4)C16—H16A0.9600
C6—C71.411 (4)C16—H16B0.9600
C7—C81.437 (4)C16—H16C0.9600
C8—C91.503 (4)C17—C181.488 (3)
C9—H9A0.9700C18—H180.9300
C9—H9B0.9700C18—C191.290 (3)
C9—C101.516 (4)C19—H190.9300
C10—H10A0.9700C19—C201.493 (3)
C10—H10B0.9700
C6—O1—H1108 (2)C11—C12—H12C109.5
C17—O2—H2A116 (4)H12A—C12—H12B109.5
C1—N1—H1A126 (3)H12A—C12—H12C109.5
C2—N1—C1109.2 (2)H12B—C12—H12C109.5
C2—N1—H1A125 (3)C11—C13—H13A109.5
C10—N2—C11109.8 (7)C11—C13—H13B109.5
C10—N2—C11A117.0 (6)C11—C13—H13C109.5
C10—N2—C14112.97 (18)H13A—C13—H13B109.5
C10—N2—H2105.3 (16)H13A—C13—H13C109.5
C11—N2—H2100.3 (17)H13B—C13—H13C109.5
C11A—N2—C14108.7 (8)N2—C11A—H11A107.0
C11A—N2—H2108.2 (17)C12A—C11A—N2116.2 (10)
C14—N2—C11122.2 (8)C12A—C11A—H11A107.0
C14—N2—H2103.7 (16)C12A—C11A—C13A112.5 (11)
N1—C1—H1B124.8C13A—C11A—N2106.7 (11)
C8—C1—N1110.4 (3)C13A—C11A—H11A107.0
C8—C1—H1B124.8C11A—C12A—H12D109.5
N1—C2—C3129.7 (3)C11A—C12A—H12E109.5
N1—C2—C7107.5 (3)C11A—C12A—H12F109.5
C3—C2—C7122.8 (3)H12D—C12A—H12E109.5
C2—C3—H3121.7H12D—C12A—H12F109.5
C4—C3—C2116.6 (3)H12E—C12A—H12F109.5
C4—C3—H3121.7C11A—C13A—H13D109.5
C3—C4—H4118.8C11A—C13A—H13E109.5
C3—C4—C5122.5 (3)C11A—C13A—H13F109.5
C5—C4—H4118.8H13D—C13A—H13E109.5
C4—C5—H5119.5H13D—C13A—H13F109.5
C6—C5—C4121.0 (3)H13E—C13A—H13F109.5
C6—C5—H5119.5N2—C14—H14106.2
O1—C6—C5123.8 (3)C15—C14—N2113.9 (3)
O1—C6—C7117.2 (2)C15—C14—H14106.2
C5—C6—C7118.9 (3)C16—C14—N2111.5 (2)
C2—C7—C6118.2 (2)C16—C14—H14106.2
C2—C7—C8107.1 (2)C16—C14—C15112.3 (3)
C6—C7—C8134.8 (2)C14—C15—H15A109.5
C1—C8—C7105.8 (2)C14—C15—H15B109.5
C1—C8—C9125.6 (3)C14—C15—H15C109.5
C7—C8—C9128.6 (2)H15A—C15—H15B109.5
C8—C9—H9A109.5H15A—C15—H15C109.5
C8—C9—H9B109.5H15B—C15—H15C109.5
C8—C9—C10110.8 (2)C14—C16—H16A109.5
H9A—C9—H9B108.1C14—C16—H16B109.5
C10—C9—H9A109.5C14—C16—H16C109.5
C10—C9—H9B109.5H16A—C16—H16B109.5
N2—C10—C9113.63 (19)H16A—C16—H16C109.5
N2—C10—H10A108.8H16B—C16—H16C109.5
N2—C10—H10B108.8O2—C17—C18114.0 (2)
C9—C10—H10A108.8O3—C17—O2125.1 (2)
C9—C10—H10B108.8O3—C17—C18120.9 (2)
H10A—C10—H10B107.7C17—C18—H18118.5
N2—C11—H11107.4C19—C18—C17123.0 (2)
C12—C11—N2112.5 (9)C19—C18—H18118.5
C12—C11—H11107.4C18—C19—H19117.8
C13—C11—N2111.5 (10)C18—C19—C20124.3 (2)
C13—C11—H11107.4C20—C19—H19117.8
C13—C11—C12110.2 (11)O4—C20—C19114.1 (2)
C11—C12—H12A109.5O5—C20—O4125.2 (2)
C11—C12—H12B109.5O5—C20—C19120.8 (2)
O1—C6—C7—C2179.3 (2)C6—C7—C8—C90.2 (5)
O1—C6—C7—C8−1.4 (4)C7—C2—C3—C40.2 (4)
O2—C17—C18—C19173.0 (3)C7—C8—C9—C1075.9 (3)
O3—C17—C18—C19−7.1 (5)C8—C9—C10—N2170.4 (2)
N1—C1—C8—C7−0.3 (3)C10—N2—C11—C12−52.0 (12)
N1—C1—C8—C9−179.5 (2)C10—N2—C11—C1372.4 (13)
N1—C2—C3—C4−179.3 (3)C10—N2—C11A—C12A−57.9 (12)
N1—C2—C7—C6179.2 (2)C10—N2—C11A—C13A68.4 (13)
N1—C2—C7—C8−0.3 (3)C10—N2—C14—C1554.5 (3)
C1—N1—C2—C3179.6 (3)C10—N2—C14—C16−177.2 (2)
C1—N1—C2—C70.1 (3)C11—N2—C10—C9−164.4 (7)
C1—C8—C9—C10−105.0 (3)C11—N2—C14—C15−80.1 (6)
C2—N1—C1—C80.1 (3)C11—N2—C14—C1648.1 (6)
C2—C3—C4—C50.3 (5)C11A—N2—C10—C9−177.3 (8)
C2—C7—C8—C10.3 (3)C11A—N2—C14—C15−77.0 (6)
C2—C7—C8—C9179.6 (2)C11A—N2—C14—C1651.2 (6)
C3—C2—C7—C6−0.3 (4)C14—N2—C10—C955.3 (3)
C3—C2—C7—C8−179.8 (3)C14—N2—C11—C1283.9 (12)
C3—C4—C5—C6−0.6 (6)C14—N2—C11—C13−151.7 (11)
C4—C5—C6—O1−178.8 (3)C14—N2—C11A—C12A71.5 (13)
C4—C5—C6—C70.5 (5)C14—N2—C11A—C13A−162.2 (12)
C5—C6—C7—C20.0 (4)C17—C18—C19—C20−177.7 (3)
C5—C6—C7—C8179.3 (3)C18—C19—C20—O4174.1 (3)
C6—C7—C8—C1−179.1 (3)C18—C19—C20—O5−6.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O4i0.91 (1)1.54 (2)2.441 (3)173 (6)
N1—H1A···O5ii0.87 (1)2.13 (2)2.989 (3)170 (4)
N2—H2···O30.90 (1)1.88 (1)2.756 (3)165 (2)
O1—H1···O5iii0.89 (1)1.89 (1)2.784 (3)177 (4)
Symmetry codes: (i) x+1, y, z; (ii) x+3/2, −y+3/2, −z+1; (iii) −x+1/2, −y+1, z−1/2.
 

Acknowledgements

Financial statements and conflict of inter­est: This study was funded by CaaMTech, Inc. ARC reports an ownership inter­est in CaaMTech, Inc., which owns US and worldwide patent applications, covering new tryptamine compounds, compositions, formulations, novel crystalline forms, and methods of making and using the same.

Funding information

Funding for this research was provided by: National Science Foundation (grant No. CHE-1429086).

References

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Volume 10| Part 6| June 2025| x250564
https://doi.org/10.1107/S2414314625005644