Exploring DMT. To explore a different substance…

Names:
DMT · Nigerine · Desoxybufotenine · Indole, 3-[2-(dimethylamino)ethyl] · Tryptamine, N,N-dimethyl · 3-[2-(Dimethylamino)ethyl]indole · N,N-Dimethyltryptamine
IUPAC name:
2-(1H-Indol-3-yl)-N,N-dimethylethan-1-amine
ID: 5006 · Formula: C12H16N2 · Molecular weight: 188.269
InChI: InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

Su, T; Hayashi, T; Vaupel, DB. When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci. Signal., 10 Mar 2009, 2 (61), 1–4. 392 kB. http://dx.doi.org/10.1126/scisignal.261pe12

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. http://dx.doi.org/10.1126/science.1166127

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. http://dx.doi.org/10.1124/mol.107.039255

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. http://dx.doi.org/10.1080/02791072.1976.10471846

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. http://dx.doi.org/10.1039/b504001a

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. http://dx.doi.org/10.1039/b413014f

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. http://dx.doi.org/10.1021/jm00353a021

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. http://dx.doi.org/10.1021/jm00321a017

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. http://dx.doi.org/10.1021/jm00190a014

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. http://dx.doi.org/10.1016/j.talanta.2007.06.012

Moura, S; Carvalho, FG; de Oliveira, CDR; Pinto, E; Yonamine, M. qNMR: An applicable method for the determination of dimethyltryptamine in ayahuasca, a psychoactive plant preparation. Phytochem. Lett., 11 Jun 2010, 3 (2), 79–83. 227 kB. http://dx.doi.org/10.1016/j.phytol.2009.12.004

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. http://dx.doi.org/10.1016/j.pbb.2007.06.001

Bõszõrményi, Z; Szára, S. Dimethyltryptamine experiments with psychotics. Br. J. Psychiatry, 1 Apr 1958, 104 (435), 445–453. 1274 kB. http://dx.doi.org/10.1192/bjp.104.435.445

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. http://dx.doi.org/10.1371/journal.pone.0009019

Szára, S. The comparison of the psychotic effect of tryptamine derivatives with the effects of mescaline and LSD-25 in self-experiments. In Psychotropic Drugs [proceedings]; Garattini, S; Ghetti, V, Eds., Elsevier, 1957; pp 460–467. 480 kB.

Shulgin, AT. DMT and tryptophan. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 19 Sep 2002.

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture, countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture, countyourculture: rational exploration of the underground, 10 Mar 2012.

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Fasanello, JA; Placke, AD. The isolation, identification, and quantitation of dimethyltryptamine (DMT) in Mimosa Hostilis. Microgram J., 1 Jan 2007, 5 (1–4), 41–52. 168 kB.

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Blackledge, RD; Taylor, CM. Psychotria viridis—A botanical source of dimethyltryptamine (DMT). Microgram J., 1 Jan 2003, 1 (1–2), 18–22. 429 kB.

Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011. 2609 kB.

Fenderson5555. DMT from tryptophan? 23 Mar 2011.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. http://dx.doi.org/10.1016/j.neuropharm.2011.01.017

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. http://dx.doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. http://dx.doi.org/10.1007/BF02818560

Szara, S; Axelrod, J. Hydroxylation and N-demethylation of N,N-dimethyltryptamine. Experientia, 1 Jun 1959, 15 (6), 216–217. 304 kB. http://dx.doi.org/10.1007/BF02158111

Szara, S. Dimethyltryptamin: Its metabolism in man; the relation to its psychotic effect to the serotonin metabolism. Experientia, 1 Jan 1956, 12 (11), 441–442. 333 kB. http://dx.doi.org/10.1007/BF02157378

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. http://dx.doi.org/10.1002/qsar.19860050404

Pires, APS; de Oliveira, CDR; Moura, S; Dõrr, FA; Silva, WAE; Yonamine, M. Gas chromatographic analysis of dimethyltryptamine and β-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage. Phytochem. Anal., 1 Mar 2009, 20 (2), 149–153. 131 kB. http://dx.doi.org/10.1002/pca.1110

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. http://dx.doi.org/10.1002/jlcr.1557

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Analysis, 2012. 270 kB. http://dx.doi.org/10.1002/dta.422

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Analysis, 1 Jan 2012, 4 (1), 24–32. 506 kB. http://dx.doi.org/10.1002/dta.398

Brandt, SD; Moore, SA; Freeman, S; Kanu, AB. Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry. Drug Test. Analysis, 1 Jul 2010, 2 (7), 330–338. 192 kB. http://dx.doi.org/10.1002/dta.142

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LCMS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. http://dx.doi.org/10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. http://dx.doi.org/10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. http://dx.doi.org/10.1002/bmc.1551

Gambelunghe, C; Aroni, K; Rossi, R; Moretti, L; Bacci, M. Identification of N,N-dimethyltryptamine and β-carbolines in psychotropic ayahuasca beverage. Biomed. Chromatogr., 1 Oct 2008, 22 (10) 1056–1059. 140 kB. http://dx.doi.org/10.1002/bmc.1023

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 24 May 2014. 298 kB. http://dx.doi.org/10.1007/s00213-014-3557-7

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. http://dx.doi.org/10.1007/s00702-009-0308-8

Brandt, SD; Martins, CP; Freeman, S; Dempster, N; Riby, PG; Gartz, J; Alder, JF. Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis. Forensic Sci. Int., 4 Jul 2008, 178 (2–3), 162–170. 785 kB. http://dx.doi.org/10.1016/j.forsciint.2008.03.013

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. http://dx.doi.org/10.1016/j.chroma.2009.10.088

Martins, CP; Freeman, S; Alder, JF; Brandt, SD. Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatographyelectrospray ionisation tandem mass spectrometry. J. Chromatogr. A, 14 Aug 2009, 1216 (33), 6119–6123. 315 kB. http://dx.doi.org/10.1016/j.chroma.2009.06.060

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DBT
DET
DIPT
DPT
EIPT
MBT
MIPT
NET
NMT
T
NIPT
N-HO-NMT
NCPT
PIPT
BIPT
MET
MPT
NPT
NBT
NIBT
NSBT
NTBT
NAT
NHT
DALT
5558
5559
N-Benzyltryptamine
5565
5566
DIBT
EPT
MIBT
MSBT
DSBT
N-Formyltryptamine
5601
5602
5603
5604
5605
5606
5607
5608
5609
5610
5611
5612
5613
5614
5615
5616
5617
5618
5619
5620
5621
5622
5623
5624
5625
5626
5627
5628
5629
5630
5631
5632
5633
5634
5635
5636
5637
5638
5639
5640
5641
5642
5643
5645
5646
5647
5648
5649
5650
5651
5652
5653
5654
DAT
DHT
HOT-T
DMT N-oxide
α,N,N-TMT
1-Me-DMT
1-MeO-DMT · Lespedamine
2-Me-DMT
4-HO-DMT · Psilocin
4-H2PO4-DMT · Psilocybin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
5-HO-DMT
5-MeO-DMT
5-MeS-DMT
5-Br-DMT
Bufoviridine
5-EtO-DMT
5-AcO-DMT
5,N,N-TMT
Sumatriptan
5-F-DMT
5-Et-DMT
5-Chloro-DMT
5-TMS-DMT
5-Ac-DMT
5-Cam-DMT
6-HO-DMT
6-MeO-DMT
6-F-DMT
6-MeS-DMT
5487
5493
6-Chloro-DMT
7-MeO-DMT
7-HO-DMT
N,N,7-TMT
7-Br-DMT
7-Et-DMT
pyr-T
pip-T
mor-T
5069
C-DMT
5073
5074
Gramine
U-6056 · DMHT
dmpyrrol-T
mepipaz-T
N-Methylhomotryptamine
Homotryptamine
2,α-DMT
α,N-DMT
α-ET
NET
1,α-DMT
α,α-DMT
4,α-DMT
7-Me-AMT
N-Methylhomotryptamine
5-Ethyltryptamine
DBT
DET
DIPT
DPT
EIPT
MBT
MIPT
NET
NMT
T
NIPT
N-HO-NMT
NCPT
PIPT
BIPT
MET
MPT
NPT
NBT
NIBT
NSBT
NTBT
NAT
NHT
DALT
5558
5559
N-Benzyltryptamine
5565
5566
DIBT
EPT
MIBT
MSBT
DSBT
N-Formyltryptamine
5601
5602
5603
5604
5605
5606
5607
5608
5609
5610
5611
5612
5613
5614
5615
5616
5617
5618
5619
5620
5621
5622
5623
5624
5625
5626
5627
5628
5629
5630
5631
5632
5633
5634
5635
5636
5637
5638
5639
5640
5641
5642
5643
5645
5646
5647
5648
5649
5650
5651
5652
5653
5654
DAT
DHT
HOT-T
DMT N-oxide
α,N,N-TMT
1-Me-DMT
1-MeO-DMT · Lespedamine
2-Me-DMT
4-HO-DMT · Psilocin
4-H2PO4-DMT · Psilocybin
4-MeO-DMT
4-MeS-DMT
4-AcO-DMT
4-Amino-DMT
4-F-DMT
5483
5484
5-HO-DMT
5-MeO-DMT
5-MeS-DMT
5-Br-DMT
Bufoviridine
5-EtO-DMT
5-AcO-DMT
5,N,N-TMT
Sumatriptan
5-F-DMT
5-Et-DMT
5-Chloro-DMT
5-TMS-DMT
5-Ac-DMT
5-Cam-DMT
6-HO-DMT
6-MeO-DMT
6-F-DMT
6-MeS-DMT
5487
5493
6-Chloro-DMT
7-MeO-DMT
7-HO-DMT
N,N,7-TMT
7-Br-DMT
7-Et-DMT
pyr-T
pip-T
mor-T
5069
C-DMT
5073
5074
Gramine
U-6056 · DMHT
dmpyrrol-T
mepipaz-T
N-Methylhomotryptamine
Homotryptamine
2,α-DMT
α,N-DMT
α-ET
NET
1,α-DMT
α,α-DMT
4,α-DMT
7-Me-AMT
N-Methylhomotryptamine
5-Ethyltryptamine
3 December 2016 · Creative Commons BY-NC-SA ·