research communications
5-Methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT): freebase and fumarate
aUniversity of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA, and bCaaMTech, LLC, 58 East Sunset Way, Suite 209, Issaquah, WA 98027, USA
*Correspondence e-mail: dmanke@umassd.edu
The solid-state structures of the synthetic psychedelic 5-methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT) {systematic name: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-amine}, C17H25N2O, and its fumarate salt, bis(5-methoxy-N,N-di-n-propyltryptammonium) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium} but-2-enedioate), 2C17H25N2O+·C4H2O42−, are reported. The freebase has a single tryptamine molecule in the The molecules are linked together by N—H⋯N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the 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 R44(22) rings, and C22(14) and C44(28) parallel chains along [001].
Keywords: crystal structure; tryptamines; indoles; hydrogen bonding.
1. Chemical context
5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a psychoactive indolealkylamine that is found in a number of plants and animals, but is best known to be present in the parotid glands of the Colorado River toad, Bufo alvarius (Shen et al., 2010). 5-MeO-DMT demonstrates high activity at the serotonin (5-hydroxytryptamine, 5-HT) 2A receptor, which leads to its psychotropic activity. Recent research has pointed to 5-MeO-DMT as a promising pharmaceutical in the treatment of mental health disorders (Uthaug et al., 2019). There are a number of synthetic N,N-dialkyl derivatives including 5-methoxy-N-methyl-N-isopropyltryptamin (5-MeO-MiPT), 5-methoxy-N,N-diethyltryptamine (5-MeO-DET), 5-methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT). Alexander Shulgin described the experience associated with inhalation of these derivatives in humans, with 5-MeO-DMT described as `positive and out-of-body' while 5-MeO-DPT was described as `good and bad' (Shulgin & Shulgin, 1997). 5-MeO-DPT has not been described much in the scientific literature, though a recent report described its activity at the 5-HT1A and 5-HT2A receptors showing 75–100% of full agonism at both receptors (Åstrand et al., 2020). As this class of compounds becomes more important for the treatment of mental health in humans, an in depth understanding of these compounds and how the structural changes impact the clinical experience in humans is going to be significant. To do so, it is important to have analytically pure, well-characterized compounds, ideally as crystalline materials. Herein we report the first structures of 5-MeO-DPT, both as its freebase and as its fumarate salt.
2. Structural commentary
The N,N-di-n-propyltryptamine (5-MeO-DPT) freebase contains a single tryptamine molecule (Fig. 1, left). It possesses a near planar indole unit with an r.m.s. deviation from planarity of 0.012 Å. The methoxy group is in the same plane as the indole ring with a C6—C5—O1—C17 torsion angle of −1.2 (2)°. The ethylamino arm is turned away from the indole plane with a C1—C8—C9—C10 torsion angle of 110.4 (2)°.
of 5-methoxy-The N,N-di-n-propyltryptammonium) fumarate contains one tryptammonium cation and half of a fumarate dianion (Fig. 1, right). The tryptammonium cation possesses a near planar indole unit with a deviation from planarity of 0.015 Å. The methoxy group is turned slightly from the plane of the indole ring with a C6—C5—O1—C17 torsion angle of −13.5 (4)°. The ethylamino arm is turned away from the indole plane with a C1—C8—C9—C10 torsion angle of −104.8 (3)°. The second half of the fumarate dianion is generated by inversion, and is near planar with an r.m.s. deviation from planarity of 0.022 Å.
of bis(5-methoxy-3. Supramolecular features
In the solid-state structure of 5-MeO-DPT freebase, the molecules are held together by an N1—H1⋯N2 hydrogen bond between the indole N—H and the amino nitrogen atom. These hydrogen bonds join the molecules together in infinite chains along the [010] direction (Table 1). The crystal packing of 5-MeO-DPT freebase is shown on the left in Fig. 2.
In the structure of 5-MeO-DPT fumarate, the tryptammonium cation is linked to the fumarate dianion in the ). The crystal packing of 5-MeO-DPT fumarate is shown on the right in Fig. 2. Two tryptammonium cations and two fumarate dianions are joined together through these hydrogen bonds to form rings with graph-set notation R44(22) (Etter et al., 1990). The rings are joined together by two parallel chains along [001]. These chains have graph-set notation C22(14) and C44(28). The chains and rings are shown in Fig. 3.
through an N2—H2⋯O3 hydrogen bond between the ammonium nitrogen and a carboxylate oxygen of the fumarate. There is also an N1—H1⋯O4 hydrogen bond between the indole nitrogen and the other oxygen of the carboxylate group on a symmetry-generated fumarate dianion (Table 24. Database survey
The two structures reported are most closely related to the freebase of 5-methoxy-N,N-diallyltryptamine, or 5-MeO-DALT (CCDC 1995802; Chadeayne et al., 2020c), and the fumarate of 5-MeO-DALT (Pham, Sammeta et al., 2021), which exhibit solid-state structures that are very similar to those reported here. The freebase of 5-MeO-DPT and 5-MeO-DALT have nearly identical unit cells. The fumarates of the two 5-MeO-DPT analogs exhibit the same chains, showing R44(22) rings and C22(14) and C44(28) chains in both cases. The other N,N-di-n-propyltryptamine structures known are 4-hydroxy-N,N-di-n-propyltryptammonium chloride (Sammeta et al., 2020) and bis(4-hydroxy-N,N-di-n-propyltryptammonium) fumarate (CCDC 1962339; Chadeayne, Pham et al., 2019). The other tryptamine freebase structures known are the natural products N,N-dimethyltryptamine, or DMT (DMTRYP; Falkenberg, 1972), 5-MeO-DMT (QQQAGY; Bergin et al., 1968), psilocybin (PSILOC; Weber & Petcher, 1974), psilocin (PSILIN; Petcher & Weber, 1974) 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 (Pham, Chadeayne et al., 2021) and psilacetin (HOCJUH; Chadeayne et al., 2019a).
5. Synthesis and crystallization
Slow evaporation of an acetone solution of a commercial sample (Chem Logix) of 5-MeO-DPT freebase resulted in the formation of crystals of 5-methoxy-N,N-di-n-propyltryptamine suitable for X-ray analysis. Crystals of bis(5-methoxy-N,N-di-n-propyltryptammonium) fumarate were grown from the slow evaporation of an acetonitrile solution of a commercial sample (Chem Logix) of 5-MeO-DPT fumarate.
6. Refinement
Crystal data, data collection and structure .
details are summarized in Table 3Supporting information
https://doi.org/10.1107/S2056989021003753/zq2261sup1.cif
contains datablocks umd2187e_a, umd2188f_a. DOI:Structure factors: contains datablock umd2187e_a. DOI: https://doi.org/10.1107/S2056989021003753/zq2261umd2187e_asup2.hkl
Structure factors: contains datablock umd2188f_a. DOI: https://doi.org/10.1107/S2056989021003753/zq2261umd2188f_asup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021003753/zq2261umd2187e_asup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989021003753/zq2261umd2188f_asup5.cml
For both structures, data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C17H26N2O | F(000) = 600 |
Mr = 274.40 | Dx = 1.132 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2223 (3) Å | Cell parameters from 9916 reflections |
b = 13.0931 (6) Å | θ = 3.3–25.6° |
c = 19.7791 (10) Å | µ = 0.07 mm−1 |
β = 91.825 (2)° | T = 297 K |
V = 1610.57 (13) Å3 | PLATE, colourless |
Z = 4 | 0.38 × 0.3 × 0.06 mm |
Bruker D8 Venture CMOS diffractometer | 2466 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.038 |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | θmax = 25.7°, θmin = 3.3° |
Tmin = 0.687, Tmax = 0.745 | h = −7→7 |
29365 measured reflections | k = −15→15 |
3035 independent reflections | l = −24→24 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.3694P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.117 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.14 e Å−3 |
3035 reflections | Δρmin = −0.17 e Å−3 |
189 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.046 (13) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.64844 (19) | 0.70622 (10) | 0.52927 (6) | 0.0702 (4) | |
N1 | 0.9733 (2) | 0.87177 (9) | 0.29883 (7) | 0.0504 (3) | |
N2 | 0.28056 (16) | 0.56376 (8) | 0.22986 (5) | 0.0412 (3) | |
C1 | 0.8201 (2) | 0.84119 (10) | 0.25168 (8) | 0.0494 (4) | |
H1A | 0.821475 | 0.857658 | 0.205961 | 0.059* | |
C2 | 0.9167 (2) | 0.83449 (10) | 0.36067 (7) | 0.0452 (3) | |
C3 | 1.0138 (2) | 0.84559 (12) | 0.42487 (8) | 0.0569 (4) | |
H3 | 1.140767 | 0.882380 | 0.430949 | 0.068* | |
C4 | 0.9172 (3) | 0.80093 (13) | 0.47864 (8) | 0.0597 (4) | |
H4 | 0.980435 | 0.807252 | 0.521685 | 0.072* | |
C5 | 0.7252 (2) | 0.74592 (11) | 0.47013 (8) | 0.0523 (4) | |
C6 | 0.6272 (2) | 0.73433 (10) | 0.40727 (7) | 0.0472 (4) | |
H6 | 0.499370 | 0.697976 | 0.401965 | 0.057* | |
C7 | 0.7248 (2) | 0.77873 (9) | 0.35118 (7) | 0.0421 (3) | |
C8 | 0.6655 (2) | 0.78344 (10) | 0.28070 (7) | 0.0442 (3) | |
C9 | 0.4698 (2) | 0.73615 (10) | 0.24763 (8) | 0.0501 (4) | |
H9A | 0.450938 | 0.763236 | 0.202185 | 0.060* | |
H9B | 0.344490 | 0.755116 | 0.272754 | 0.060* | |
C10 | 0.4834 (2) | 0.61913 (10) | 0.24396 (7) | 0.0429 (3) | |
H10A | 0.583107 | 0.601344 | 0.209131 | 0.051* | |
H10B | 0.544432 | 0.594539 | 0.286666 | 0.051* | |
C11 | 0.1721 (2) | 0.60049 (11) | 0.16734 (7) | 0.0476 (4) | |
H11A | 0.279545 | 0.613815 | 0.133983 | 0.057* | |
H11B | 0.100723 | 0.664575 | 0.176709 | 0.057* | |
C12 | 0.0078 (2) | 0.52602 (12) | 0.13767 (8) | 0.0530 (4) | |
H12A | 0.080879 | 0.464283 | 0.124003 | 0.064* | |
H12B | −0.092372 | 0.507608 | 0.172213 | 0.064* | |
C13 | −0.1154 (4) | 0.56964 (18) | 0.07758 (10) | 0.0941 (7) | |
H13A | −0.216369 | 0.519855 | 0.060362 | 0.141* | |
H13B | −0.017190 | 0.587135 | 0.042962 | 0.141* | |
H13C | −0.191324 | 0.629728 | 0.091108 | 0.141* | |
C14 | 0.1352 (2) | 0.56727 (12) | 0.28718 (7) | 0.0508 (4) | |
H14A | −0.007626 | 0.547160 | 0.271228 | 0.061* | |
H14B | 0.126623 | 0.637215 | 0.303036 | 0.061* | |
C15 | 0.2017 (3) | 0.50025 (12) | 0.34569 (8) | 0.0598 (4) | |
H15A | 0.339619 | 0.523201 | 0.364219 | 0.072* | |
H15B | 0.218942 | 0.430741 | 0.329783 | 0.072* | |
C16 | 0.0390 (3) | 0.50174 (17) | 0.40067 (10) | 0.0814 (6) | |
H16A | 0.084291 | 0.456110 | 0.436343 | 0.122* | |
H16B | −0.098413 | 0.480319 | 0.382311 | 0.122* | |
H16C | 0.027543 | 0.569755 | 0.418335 | 0.122* | |
C17 | 0.4531 (3) | 0.65147 (16) | 0.52456 (10) | 0.0800 (6) | |
H17A | 0.414835 | 0.629014 | 0.568787 | 0.120* | |
H17B | 0.469744 | 0.593254 | 0.495692 | 0.120* | |
H17C | 0.341808 | 0.694924 | 0.505997 | 0.120* | |
H1 | 1.073 (3) | 0.9177 (14) | 0.2916 (9) | 0.066 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0744 (8) | 0.0789 (8) | 0.0573 (7) | 0.0026 (6) | 0.0055 (6) | 0.0104 (6) |
N1 | 0.0454 (7) | 0.0430 (7) | 0.0630 (8) | −0.0051 (5) | 0.0051 (6) | −0.0007 (6) |
N2 | 0.0352 (5) | 0.0404 (6) | 0.0482 (6) | 0.0007 (4) | 0.0025 (4) | 0.0014 (5) |
C1 | 0.0542 (8) | 0.0387 (7) | 0.0554 (8) | 0.0021 (6) | 0.0036 (7) | −0.0006 (6) |
C2 | 0.0399 (7) | 0.0370 (7) | 0.0587 (8) | 0.0038 (5) | 0.0017 (6) | −0.0042 (6) |
C3 | 0.0425 (7) | 0.0584 (9) | 0.0691 (10) | −0.0016 (7) | −0.0065 (7) | −0.0082 (8) |
C4 | 0.0540 (9) | 0.0680 (10) | 0.0564 (9) | 0.0060 (8) | −0.0074 (7) | −0.0066 (8) |
C5 | 0.0527 (8) | 0.0495 (8) | 0.0550 (9) | 0.0098 (7) | 0.0039 (7) | 0.0013 (7) |
C6 | 0.0435 (7) | 0.0394 (7) | 0.0587 (9) | 0.0014 (6) | 0.0013 (6) | 0.0002 (6) |
C7 | 0.0387 (7) | 0.0320 (6) | 0.0555 (8) | 0.0045 (5) | 0.0010 (6) | −0.0035 (6) |
C8 | 0.0446 (7) | 0.0319 (6) | 0.0559 (8) | 0.0032 (5) | −0.0008 (6) | −0.0030 (6) |
C9 | 0.0487 (8) | 0.0392 (7) | 0.0616 (9) | 0.0025 (6) | −0.0092 (6) | −0.0008 (6) |
C10 | 0.0363 (7) | 0.0395 (7) | 0.0528 (8) | 0.0019 (5) | 0.0013 (5) | −0.0017 (6) |
C11 | 0.0469 (7) | 0.0464 (8) | 0.0493 (8) | −0.0055 (6) | −0.0007 (6) | 0.0040 (6) |
C12 | 0.0456 (8) | 0.0514 (8) | 0.0617 (9) | −0.0052 (6) | −0.0030 (6) | 0.0013 (7) |
C13 | 0.0982 (15) | 0.1021 (16) | 0.0794 (13) | −0.0435 (13) | −0.0369 (11) | 0.0253 (12) |
C14 | 0.0422 (7) | 0.0563 (9) | 0.0543 (8) | 0.0048 (6) | 0.0060 (6) | 0.0050 (7) |
C15 | 0.0695 (10) | 0.0524 (9) | 0.0579 (9) | 0.0011 (8) | 0.0090 (7) | 0.0071 (7) |
C16 | 0.0866 (13) | 0.0960 (15) | 0.0627 (11) | −0.0025 (11) | 0.0185 (9) | 0.0148 (10) |
C17 | 0.0822 (12) | 0.0812 (13) | 0.0773 (12) | −0.0058 (10) | 0.0137 (10) | 0.0226 (10) |
O1—C5 | 1.3794 (18) | C10—H10A | 0.9700 |
O1—C17 | 1.412 (2) | C10—H10B | 0.9700 |
N1—C1 | 1.3716 (19) | C11—H11A | 0.9700 |
N1—C2 | 1.3734 (19) | C11—H11B | 0.9700 |
N1—H1 | 0.878 (18) | C11—C12 | 1.5171 (19) |
N2—C10 | 1.4745 (16) | C12—H12A | 0.9700 |
N2—C11 | 1.4705 (17) | C12—H12B | 0.9700 |
N2—C14 | 1.4735 (17) | C12—C13 | 1.506 (2) |
C1—H1A | 0.9300 | C13—H13A | 0.9600 |
C1—C8 | 1.364 (2) | C13—H13B | 0.9600 |
C2—C3 | 1.396 (2) | C13—H13C | 0.9600 |
C2—C7 | 1.4070 (18) | C14—H14A | 0.9700 |
C3—H3 | 0.9300 | C14—H14B | 0.9700 |
C3—C4 | 1.369 (2) | C14—C15 | 1.500 (2) |
C4—H4 | 0.9300 | C15—H15A | 0.9700 |
C4—C5 | 1.401 (2) | C15—H15B | 0.9700 |
C5—C6 | 1.376 (2) | C15—C16 | 1.510 (2) |
C6—H6 | 0.9300 | C16—H16A | 0.9600 |
C6—C7 | 1.4071 (19) | C16—H16B | 0.9600 |
C7—C8 | 1.4318 (19) | C16—H16C | 0.9600 |
C8—C9 | 1.4980 (19) | C17—H17A | 0.9600 |
C9—H9A | 0.9700 | C17—H17B | 0.9600 |
C9—H9B | 0.9700 | C17—H17C | 0.9600 |
C9—C10 | 1.5363 (18) | ||
C5—O1—C17 | 117.15 (13) | N2—C11—H11A | 108.8 |
C1—N1—C2 | 108.02 (12) | N2—C11—H11B | 108.8 |
C1—N1—H1 | 124.6 (11) | N2—C11—C12 | 113.62 (11) |
C2—N1—H1 | 126.2 (11) | H11A—C11—H11B | 107.7 |
C11—N2—C10 | 111.44 (10) | C12—C11—H11A | 108.8 |
C11—N2—C14 | 111.12 (10) | C12—C11—H11B | 108.8 |
C14—N2—C10 | 112.44 (11) | C11—C12—H12A | 109.1 |
N1—C1—H1A | 124.5 | C11—C12—H12B | 109.1 |
C8—C1—N1 | 111.08 (13) | H12A—C12—H12B | 107.9 |
C8—C1—H1A | 124.5 | C13—C12—C11 | 112.43 (13) |
N1—C2—C3 | 131.08 (13) | C13—C12—H12A | 109.1 |
N1—C2—C7 | 107.83 (12) | C13—C12—H12B | 109.1 |
C3—C2—C7 | 121.08 (14) | C12—C13—H13A | 109.5 |
C2—C3—H3 | 120.8 | C12—C13—H13B | 109.5 |
C4—C3—C2 | 118.30 (14) | C12—C13—H13C | 109.5 |
C4—C3—H3 | 120.8 | H13A—C13—H13B | 109.5 |
C3—C4—H4 | 119.3 | H13A—C13—H13C | 109.5 |
C3—C4—C5 | 121.32 (15) | H13B—C13—H13C | 109.5 |
C5—C4—H4 | 119.3 | N2—C14—H14A | 108.6 |
O1—C5—C4 | 114.14 (14) | N2—C14—H14B | 108.6 |
C6—C5—O1 | 124.69 (14) | N2—C14—C15 | 114.48 (12) |
C6—C5—C4 | 121.16 (14) | H14A—C14—H14B | 107.6 |
C5—C6—H6 | 120.8 | C15—C14—H14A | 108.6 |
C5—C6—C7 | 118.48 (13) | C15—C14—H14B | 108.6 |
C7—C6—H6 | 120.8 | C14—C15—H15A | 109.2 |
C2—C7—C6 | 119.65 (13) | C14—C15—H15B | 109.2 |
C2—C7—C8 | 107.37 (12) | C14—C15—C16 | 111.92 (14) |
C6—C7—C8 | 132.94 (12) | H15A—C15—H15B | 107.9 |
C1—C8—C7 | 105.68 (12) | C16—C15—H15A | 109.2 |
C1—C8—C9 | 128.30 (14) | C16—C15—H15B | 109.2 |
C7—C8—C9 | 126.00 (13) | C15—C16—H16A | 109.5 |
C8—C9—H9A | 109.0 | C15—C16—H16B | 109.5 |
C8—C9—H9B | 109.0 | C15—C16—H16C | 109.5 |
C8—C9—C10 | 112.80 (11) | H16A—C16—H16B | 109.5 |
H9A—C9—H9B | 107.8 | H16A—C16—H16C | 109.5 |
C10—C9—H9A | 109.0 | H16B—C16—H16C | 109.5 |
C10—C9—H9B | 109.0 | O1—C17—H17A | 109.5 |
N2—C10—C9 | 116.81 (11) | O1—C17—H17B | 109.5 |
N2—C10—H10A | 108.1 | O1—C17—H17C | 109.5 |
N2—C10—H10B | 108.1 | H17A—C17—H17B | 109.5 |
C9—C10—H10A | 108.1 | H17A—C17—H17C | 109.5 |
C9—C10—H10B | 108.1 | H17B—C17—H17C | 109.5 |
H10A—C10—H10B | 107.3 | ||
O1—C5—C6—C7 | −179.67 (13) | C3—C4—C5—C6 | 0.3 (2) |
N1—C1—C8—C7 | 0.81 (15) | C4—C5—C6—C7 | 0.3 (2) |
N1—C1—C8—C9 | 179.30 (13) | C5—C6—C7—C2 | −0.84 (19) |
N1—C2—C3—C4 | 178.54 (14) | C5—C6—C7—C8 | −178.36 (13) |
N1—C2—C7—C6 | −178.18 (11) | C6—C7—C8—C1 | 177.31 (14) |
N1—C2—C7—C8 | −0.08 (14) | C6—C7—C8—C9 | −1.2 (2) |
N2—C11—C12—C13 | 174.55 (15) | C7—C2—C3—C4 | −0.1 (2) |
N2—C14—C15—C16 | −176.15 (14) | C7—C8—C9—C10 | −71.42 (18) |
C1—N1—C2—C3 | −178.24 (14) | C8—C9—C10—N2 | 163.85 (12) |
C1—N1—C2—C7 | 0.57 (15) | C10—N2—C11—C12 | 160.69 (11) |
C1—C8—C9—C10 | 110.38 (16) | C10—N2—C14—C15 | −74.13 (16) |
C2—N1—C1—C8 | −0.88 (16) | C11—N2—C10—C9 | 55.06 (16) |
C2—C3—C4—C5 | −0.4 (2) | C11—N2—C14—C15 | 160.17 (13) |
C2—C7—C8—C1 | −0.44 (14) | C14—N2—C10—C9 | −70.46 (15) |
C2—C7—C8—C9 | −178.97 (12) | C14—N2—C11—C12 | −73.06 (15) |
C3—C2—C7—C6 | 0.77 (19) | C17—O1—C5—C4 | 178.83 (15) |
C3—C2—C7—C8 | 178.88 (12) | C17—O1—C5—C6 | −1.2 (2) |
C3—C4—C5—O1 | −179.69 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.878 (18) | 2.167 (19) | 3.0070 (17) | 160.0 (16) |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
C17H27N2O+·0.5C4H2O42− | Z = 2 |
Mr = 332.43 | F(000) = 360 |
Triclinic, P1 | Dx = 1.171 Mg m−3 |
a = 9.2956 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.4443 (6) Å | Cell parameters from 9966 reflections |
c = 12.7427 (8) Å | θ = 2.6–25.6° |
α = 78.552 (2)° | µ = 0.08 mm−1 |
β = 75.929 (2)° | T = 297 K |
γ = 60.806 (2)° | BLOCK, colourless |
V = 943.06 (11) Å3 | 0.3 × 0.22 × 0.2 mm |
Bruker D8 Venture CMOS diffractometer | 3006 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.032 |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | θmax = 25.8°, θmin = 2.6° |
Tmin = 0.722, Tmax = 0.745 | h = −11→11 |
37231 measured reflections | k = −11→11 |
3565 independent reflections | l = −15→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0652P)2 + 0.3068P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3565 reflections | Δρmax = 0.29 e Å−3 |
228 parameters | Δρmin = −0.15 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.12338 (18) | 0.1921 (2) | 0.42565 (12) | 0.0820 (5) | |
O3 | 0.56136 (18) | 0.70109 (14) | 0.91994 (11) | 0.0619 (4) | |
O4 | 0.38521 (19) | 0.94777 (15) | 0.85790 (10) | 0.0619 (4) | |
N1 | 0.6457 (2) | 0.7968 (2) | 0.29933 (12) | 0.0592 (4) | |
N2 | 0.45383 (17) | 0.62296 (15) | 0.77576 (10) | 0.0428 (3) | |
C1 | 0.5216 (3) | 0.8238 (2) | 0.38795 (14) | 0.0569 (5) | |
H1A | 0.419516 | 0.917793 | 0.395103 | 0.068* | |
C2 | 0.7767 (2) | 0.6468 (2) | 0.31704 (13) | 0.0494 (4) | |
C3 | 0.9290 (3) | 0.5609 (3) | 0.25118 (14) | 0.0611 (5) | |
H3 | 0.955315 | 0.605071 | 0.181743 | 0.073* | |
C4 | 1.0389 (2) | 0.4104 (3) | 0.29047 (15) | 0.0635 (5) | |
H4 | 1.140948 | 0.351877 | 0.247161 | 0.076* | |
C5 | 1.0004 (2) | 0.3427 (2) | 0.39518 (15) | 0.0564 (4) | |
C6 | 0.8487 (2) | 0.4243 (2) | 0.45998 (13) | 0.0497 (4) | |
H6 | 0.822409 | 0.377642 | 0.528497 | 0.060* | |
C7 | 0.7346 (2) | 0.5788 (2) | 0.42102 (12) | 0.0450 (4) | |
C8 | 0.5686 (2) | 0.6934 (2) | 0.46471 (13) | 0.0474 (4) | |
C9 | 0.4679 (2) | 0.6678 (2) | 0.57159 (13) | 0.0477 (4) | |
H9A | 0.480231 | 0.558342 | 0.579746 | 0.057* | |
H9B | 0.350672 | 0.743536 | 0.570911 | 0.057* | |
C10 | 0.5191 (2) | 0.6913 (2) | 0.66834 (12) | 0.0470 (4) | |
H10A | 0.640253 | 0.639174 | 0.658321 | 0.056* | |
H10B | 0.478562 | 0.806815 | 0.670881 | 0.056* | |
C11 | 0.2669 (2) | 0.7020 (2) | 0.79912 (13) | 0.0506 (4) | |
H11A | 0.228284 | 0.658211 | 0.755537 | 0.061* | |
H11B | 0.223555 | 0.817953 | 0.777702 | 0.061* | |
C12 | 0.1977 (3) | 0.6766 (3) | 0.91717 (16) | 0.0767 (6) | |
H12A | 0.232415 | 0.561287 | 0.936852 | 0.092* | |
H12B | 0.244506 | 0.711049 | 0.961289 | 0.092* | |
C13 | 0.0122 (3) | 0.7678 (4) | 0.9418 (2) | 0.1035 (10) | |
H13A | −0.026624 | 0.732314 | 1.013936 | 0.155* | |
H13B | −0.034648 | 0.747832 | 0.890459 | 0.155* | |
H13C | −0.021980 | 0.882313 | 0.937002 | 0.155* | |
C14 | 0.5291 (2) | 0.44102 (19) | 0.78992 (14) | 0.0502 (4) | |
H14A | 0.504193 | 0.405008 | 0.733484 | 0.060* | |
H14B | 0.477479 | 0.408059 | 0.859428 | 0.060* | |
C15 | 0.7152 (2) | 0.3582 (2) | 0.78522 (16) | 0.0616 (5) | |
H15A | 0.740808 | 0.395586 | 0.840557 | 0.074* | |
H15B | 0.767606 | 0.388253 | 0.714986 | 0.074* | |
C16 | 0.7866 (3) | 0.1758 (3) | 0.8025 (2) | 0.0940 (8) | |
H16A | 0.906071 | 0.127238 | 0.795009 | 0.141* | |
H16B | 0.758181 | 0.138666 | 0.749425 | 0.141* | |
H16C | 0.741153 | 0.145089 | 0.874057 | 0.141* | |
C17 | 1.1057 (3) | 0.1353 (3) | 0.5365 (2) | 0.0943 (8) | |
H17A | 1.209504 | 0.044150 | 0.551443 | 0.141* | |
H17B | 1.019527 | 0.101981 | 0.553796 | 0.141* | |
H17C | 1.076098 | 0.220867 | 0.579927 | 0.141* | |
C18 | 0.4904 (2) | 0.85411 (19) | 0.91702 (12) | 0.0450 (4) | |
C19 | 0.5356 (2) | 0.92260 (19) | 0.99289 (13) | 0.0459 (4) | |
H19 | 0.619664 | 0.850477 | 1.032462 | 0.055* | |
H2 | 0.488 (3) | 0.653 (3) | 0.8317 (18) | 0.076 (6)* | |
H1 | 0.632 (3) | 0.872 (3) | 0.247 (2) | 0.082 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0612 (9) | 0.0809 (10) | 0.0683 (9) | −0.0035 (7) | −0.0085 (7) | −0.0156 (8) |
O3 | 0.0872 (9) | 0.0419 (7) | 0.0638 (8) | −0.0273 (6) | −0.0301 (7) | −0.0058 (5) |
O4 | 0.0964 (10) | 0.0497 (7) | 0.0545 (7) | −0.0402 (7) | −0.0335 (7) | 0.0072 (5) |
N1 | 0.0791 (11) | 0.0579 (9) | 0.0412 (8) | −0.0367 (9) | −0.0112 (7) | 0.0089 (7) |
N2 | 0.0549 (8) | 0.0428 (7) | 0.0346 (6) | −0.0256 (6) | −0.0093 (6) | −0.0018 (5) |
C1 | 0.0699 (12) | 0.0494 (10) | 0.0460 (9) | −0.0234 (9) | −0.0121 (8) | −0.0018 (7) |
C2 | 0.0618 (10) | 0.0595 (10) | 0.0377 (8) | −0.0384 (9) | −0.0076 (7) | 0.0000 (7) |
C3 | 0.0678 (12) | 0.0912 (15) | 0.0387 (9) | −0.0523 (11) | 0.0002 (8) | −0.0052 (9) |
C4 | 0.0516 (10) | 0.0923 (15) | 0.0507 (10) | −0.0368 (11) | 0.0031 (8) | −0.0204 (10) |
C5 | 0.0494 (10) | 0.0653 (11) | 0.0528 (10) | −0.0225 (9) | −0.0094 (8) | −0.0125 (8) |
C6 | 0.0530 (9) | 0.0553 (10) | 0.0389 (8) | −0.0253 (8) | −0.0057 (7) | −0.0027 (7) |
C7 | 0.0528 (9) | 0.0508 (9) | 0.0366 (8) | −0.0290 (8) | −0.0062 (7) | −0.0034 (6) |
C8 | 0.0589 (10) | 0.0483 (9) | 0.0382 (8) | −0.0269 (8) | −0.0091 (7) | −0.0039 (6) |
C9 | 0.0522 (9) | 0.0518 (9) | 0.0401 (8) | −0.0246 (8) | −0.0066 (7) | −0.0069 (7) |
C10 | 0.0602 (10) | 0.0447 (8) | 0.0402 (8) | −0.0278 (8) | −0.0094 (7) | −0.0021 (6) |
C11 | 0.0560 (10) | 0.0518 (9) | 0.0417 (8) | −0.0234 (8) | −0.0094 (7) | −0.0020 (7) |
C12 | 0.0666 (13) | 0.0915 (16) | 0.0490 (11) | −0.0273 (12) | −0.0023 (9) | 0.0073 (10) |
C13 | 0.0757 (16) | 0.114 (2) | 0.0622 (14) | −0.0133 (15) | 0.0082 (12) | 0.0053 (13) |
C14 | 0.0616 (10) | 0.0422 (9) | 0.0496 (9) | −0.0266 (8) | −0.0120 (8) | 0.0001 (7) |
C15 | 0.0619 (11) | 0.0588 (11) | 0.0547 (10) | −0.0233 (9) | −0.0086 (8) | 0.0003 (8) |
C16 | 0.0797 (16) | 0.0574 (13) | 0.1040 (19) | −0.0150 (12) | 0.0017 (14) | 0.0112 (12) |
C17 | 0.0861 (17) | 0.0747 (15) | 0.0759 (16) | 0.0002 (13) | −0.0186 (13) | −0.0065 (12) |
C18 | 0.0623 (10) | 0.0445 (9) | 0.0353 (7) | −0.0316 (8) | −0.0082 (7) | −0.0003 (6) |
C19 | 0.0571 (10) | 0.0450 (8) | 0.0415 (8) | −0.0280 (7) | −0.0102 (7) | −0.0024 (6) |
O1—C5 | 1.375 (2) | C10—H10A | 0.9700 |
O1—C17 | 1.408 (3) | C10—H10B | 0.9700 |
O3—C18 | 1.2592 (19) | C11—H11A | 0.9700 |
O4—C18 | 1.247 (2) | C11—H11B | 0.9700 |
N1—C1 | 1.365 (2) | C11—C12 | 1.507 (2) |
N1—C2 | 1.365 (2) | C12—H12A | 0.9700 |
N1—H1 | 0.86 (2) | C12—H12B | 0.9700 |
N2—C10 | 1.512 (2) | C12—C13 | 1.486 (3) |
N2—C11 | 1.496 (2) | C13—H13A | 0.9600 |
N2—C14 | 1.497 (2) | C13—H13B | 0.9600 |
N2—H2 | 0.98 (2) | C13—H13C | 0.9600 |
C1—H1A | 0.9300 | C14—H14A | 0.9700 |
C1—C8 | 1.367 (2) | C14—H14B | 0.9700 |
C2—C3 | 1.392 (3) | C14—C15 | 1.503 (3) |
C2—C7 | 1.406 (2) | C15—H15A | 0.9700 |
C3—H3 | 0.9300 | C15—H15B | 0.9700 |
C3—C4 | 1.365 (3) | C15—C16 | 1.504 (3) |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.404 (3) | C16—H16B | 0.9600 |
C5—C6 | 1.375 (2) | C16—H16C | 0.9600 |
C6—H6 | 0.9300 | C17—H17A | 0.9600 |
C6—C7 | 1.400 (2) | C17—H17B | 0.9600 |
C7—C8 | 1.433 (2) | C17—H17C | 0.9600 |
C8—C9 | 1.503 (2) | C18—C19 | 1.497 (2) |
C9—H9A | 0.9700 | C19—C19i | 1.308 (3) |
C9—H9B | 0.9700 | C19—H19 | 0.9300 |
C9—C10 | 1.514 (2) | ||
C5—O1—C17 | 116.90 (16) | N2—C11—H11B | 109.0 |
C1—N1—H1 | 119.0 (17) | N2—C11—C12 | 113.04 (14) |
C2—N1—C1 | 108.73 (15) | H11A—C11—H11B | 107.8 |
C2—N1—H1 | 132.3 (17) | C12—C11—H11A | 109.0 |
C10—N2—H2 | 105.8 (13) | C12—C11—H11B | 109.0 |
C11—N2—C10 | 112.05 (12) | C11—C12—H12A | 109.0 |
C11—N2—C14 | 111.85 (13) | C11—C12—H12B | 109.0 |
C11—N2—H2 | 106.2 (13) | H12A—C12—H12B | 107.8 |
C14—N2—C10 | 114.43 (12) | C13—C12—C11 | 112.83 (18) |
C14—N2—H2 | 105.8 (13) | C13—C12—H12A | 109.0 |
N1—C1—H1A | 124.8 | C13—C12—H12B | 109.0 |
N1—C1—C8 | 110.45 (17) | C12—C13—H13A | 109.5 |
C8—C1—H1A | 124.8 | C12—C13—H13B | 109.5 |
N1—C2—C3 | 131.24 (16) | C12—C13—H13C | 109.5 |
N1—C2—C7 | 107.90 (15) | H13A—C13—H13B | 109.5 |
C3—C2—C7 | 120.85 (17) | H13A—C13—H13C | 109.5 |
C2—C3—H3 | 120.6 | H13B—C13—H13C | 109.5 |
C4—C3—C2 | 118.74 (16) | N2—C14—H14A | 108.9 |
C4—C3—H3 | 120.6 | N2—C14—H14B | 108.9 |
C3—C4—H4 | 119.5 | N2—C14—C15 | 113.16 (14) |
C3—C4—C5 | 121.06 (17) | H14A—C14—H14B | 107.8 |
C5—C4—H4 | 119.5 | C15—C14—H14A | 108.9 |
O1—C5—C4 | 115.19 (17) | C15—C14—H14B | 108.9 |
O1—C5—C6 | 123.99 (17) | C14—C15—H15A | 109.2 |
C6—C5—C4 | 120.82 (18) | C14—C15—H15B | 109.2 |
C5—C6—H6 | 120.6 | C14—C15—C16 | 111.96 (18) |
C5—C6—C7 | 118.85 (16) | H15A—C15—H15B | 107.9 |
C7—C6—H6 | 120.6 | C16—C15—H15A | 109.2 |
C2—C7—C8 | 106.94 (15) | C16—C15—H15B | 109.2 |
C6—C7—C2 | 119.63 (15) | C15—C16—H16A | 109.5 |
C6—C7—C8 | 133.41 (15) | C15—C16—H16B | 109.5 |
C1—C8—C7 | 105.96 (15) | C15—C16—H16C | 109.5 |
C1—C8—C9 | 128.30 (17) | H16A—C16—H16B | 109.5 |
C7—C8—C9 | 125.70 (15) | H16A—C16—H16C | 109.5 |
C8—C9—H9A | 108.9 | H16B—C16—H16C | 109.5 |
C8—C9—H9B | 108.9 | O1—C17—H17A | 109.5 |
C8—C9—C10 | 113.31 (14) | O1—C17—H17B | 109.5 |
H9A—C9—H9B | 107.7 | O1—C17—H17C | 109.5 |
C10—C9—H9A | 108.9 | H17A—C17—H17B | 109.5 |
C10—C9—H9B | 108.9 | H17A—C17—H17C | 109.5 |
N2—C10—C9 | 113.69 (13) | H17B—C17—H17C | 109.5 |
N2—C10—H10A | 108.8 | O3—C18—C19 | 115.90 (14) |
N2—C10—H10B | 108.8 | O4—C18—O3 | 124.28 (15) |
C9—C10—H10A | 108.8 | O4—C18—C19 | 119.80 (14) |
C9—C10—H10B | 108.8 | C18—C19—H19 | 117.9 |
H10A—C10—H10B | 107.7 | C19i—C19—C18 | 124.2 (2) |
N2—C11—H11A | 109.0 | C19i—C19—H19 | 117.9 |
O1—C5—C6—C7 | 178.60 (17) | C3—C4—C5—O1 | −178.61 (17) |
O3—C18—C19—C19i | −174.3 (2) | C3—C4—C5—C6 | 1.8 (3) |
O4—C18—C19—C19i | 4.2 (3) | C4—C5—C6—C7 | −1.9 (3) |
N1—C1—C8—C7 | 1.0 (2) | C5—C6—C7—C2 | 0.2 (2) |
N1—C1—C8—C9 | −176.59 (16) | C5—C6—C7—C8 | 178.52 (17) |
N1—C2—C3—C4 | 179.92 (18) | C6—C7—C8—C1 | 179.95 (18) |
N1—C2—C7—C6 | −179.66 (15) | C6—C7—C8—C9 | −2.4 (3) |
N1—C2—C7—C8 | 1.61 (18) | C7—C2—C3—C4 | −1.6 (3) |
N2—C11—C12—C13 | 174.7 (2) | C7—C8—C9—C10 | 78.1 (2) |
N2—C14—C15—C16 | 178.56 (17) | C8—C9—C10—N2 | −164.36 (13) |
C1—N1—C2—C3 | 177.59 (18) | C10—N2—C11—C12 | −162.09 (16) |
C1—N1—C2—C7 | −1.0 (2) | C10—N2—C14—C15 | 60.72 (19) |
C1—C8—C9—C10 | −104.8 (2) | C11—N2—C10—C9 | −60.66 (18) |
C2—N1—C1—C8 | 0.0 (2) | C11—N2—C14—C15 | −170.49 (14) |
C2—C3—C4—C5 | 0.0 (3) | C14—N2—C10—C9 | 68.03 (18) |
C2—C7—C8—C1 | −1.58 (19) | C14—N2—C11—C12 | 67.9 (2) |
C2—C7—C8—C9 | 176.07 (15) | C17—O1—C5—C4 | 166.9 (2) |
C3—C2—C7—C6 | 1.5 (2) | C17—O1—C5—C6 | −13.5 (3) |
C3—C2—C7—C8 | −177.18 (15) |
Symmetry code: (i) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3 | 0.98 (2) | 1.68 (2) | 2.6588 (17) | 175 (2) |
N1—H1···O4ii | 0.86 (2) | 1.91 (3) | 2.757 (2) | 171 (2) |
Symmetry code: (ii) −x+1, −y+2, −z+1. |
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, Directorate for Mathematical and Physical Sciences (grant No. CHE-1429086).
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