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. https://doi.org/10.1007/BF02157378 #DMT
Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1.1 MB. https://doi.org/10.1016/0028-3908(62)90015-1 #DMT
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. https://doi.org/10.1007/s00702-009-0308-8
Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #DMT
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.
Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. https://doi.org/10.1016/j.bmc.2008.02.033 #13
Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. https://doi.org/10.1371/journal.pone.0009019
Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. https://doi.org/10.1002/dta.398
Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3), 364–381. 817 kB. https://doi.org/10.1016/j.neuropharm.2011.01.017
Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture, countyourculture: rational exploration of the underground, 10 Mar 2012.
Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture, countyourculture: rational exploration of the underground, 5 Dec 2011.
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. https://doi.org/10.1016/j.talanta.2007.06.012
Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. https://doi.org/10.1016/0014-2999(88)90432-3
Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. https://doi.org/10.1016/0006-2952(83)90281-2 #DMT
Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3.1 MB. https://doi.org/10.1007/BF02818560
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. https://doi.org/10.1002/jlcr.1557
Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. https://doi.org/10.1016/S0376-8716(99)00148-9
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. https://doi.org/10.1039/b504001a
Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. https://doi.org/10.1016/S0920-9964(97)00116-3
Bõszõrményi, Z; Szára, S. Dimethyltryptamine experiments with psychotics. Br. J. Psychiatry, 1 Apr 1958, 104 (435), 445–453. 1.3 MB. https://doi.org/10.1192/bjp.104.435.445
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. https://doi.org/10.1021/jm00353a021 #7
Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. https://doi.org/10.1021/jm00190a014 #1
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. https://doi.org/10.1016/j.pbb.2007.06.001
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. https://doi.org/10.1124/mol.107.039255
Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Apr 1976, 8 (2), 167–169. 1.4 MB. https://doi.org/10.1080/02791072.1976.10471846
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. https://doi.org/10.1126/science.1166127
McKenna, DJ. Monoamine oxidsase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12.2 MB. LC,MS,UV,TLC
Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 1 Jul 2012, 4 (7-8), 617-635. 270 kB. https://doi.org/10.1002/dta.422
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, 21 Feb 2005, 130 (3), 330–344. 403 kB. https://doi.org/10.1039/b413014f
Martins, CPB; Freeman, S; Alder, JF; Brandt, SD. Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry. J. Chromatogr. A, 14 Aug 2009, 1216 (33), 6119–6123. 315 kB. https://doi.org/10.1016/j.chroma.2009.06.060 #2 LC,MS,NMR
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. https://doi.org/10.1126/scisignal.261pe12
Strassman, RJ. Human psychopharmacology of N,N,-dimethyltryptamine. Behav. Brain Res., 15 Dec 1995, 73 (1–2), 121–124. 396 kB. https://doi.org/10.1016/0166-4328(96)00081-2
McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. https://doi.org/10.1016/0028-3908(90)90001-8
Szara, S; Axelrod, J. Hydroxylation and N-demethylation of N,N-dimethyltryptamine. Experientia, 1 Jun 1959, 15 (6), 216–217. 304 kB. https://doi.org/10.1007/BF02158111
Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. https://doi.org/10.1021/jm00321a017 #9
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., 1 Jan 1986, 5 (4), 153–157. 577 kB. https://doi.org/10.1002/qsar.19860050404 #2
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. 2.3 MB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.
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. https://doi.org/10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B
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. https://doi.org/10.1016/j.chroma.2009.10.088
Fenderson5555. DMT from tryptophan? , 23 Mar 2011. . Fenderson5555 3.9 MB. Big hug to W. Snow for kindly filling this gap in the collection.
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. Anal., 1 Jul 2010, 2 (7), 330–338. 192 kB. https://doi.org/10.1002/dta.142
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. https://doi.org/10.1002/pca.1110
Brandt, SD; Martins, CPB; 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. https://doi.org/10.1016/j.forsciint.2008.03.013
Gaujac, A; Martinez, ST; Gomes, AA; de Andrade, SJ; da Cunha Pinto, A; David, JM; Navickiene, S; de Andrade, JB. Application of analytical methods for the structural characterization and purity assessment of N,N-dimethyltryptamine, a potent psychedelic agent isolated from Mimosa tenuiflora inner barks. Microchem. J., 1 Jul 2013, 109, 78-83. 673 kB. https://doi.org/10.1016/j.microc.2012.03.033
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. https://doi.org/10.1016/j.phytol.2009.12.004
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, 1 Jan 1957; pp 460–467. 480 kB. #DMT
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. https://doi.org/10.1002/bmc.1023
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. 1.0 MB. https://doi.org/10.1002/bmc.1551
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. https://doi.org/10.1002/bmc.1657
Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 1 Dec 2013, 27 (12), 1690-1700. 929 kB. https://doi.org/10.1002/bmc.2981
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. 1.6 MB.
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. #DMT GC,LC,MS,NMR,IR
Blackledge, RD; Taylor, CM. Psychotria viridis—A botanical source of dimethyltryptamine (DMT). Microgram J., 1 Jan 2003, 1 (1–2), 18–22. 429 kB.
Gaujac, A; Ford, JL; Dempster, NM; de Andrade, JB; Brandt, SD. Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry. Microchem. J., 1 Sep 2013, 110, 146–157. 1.2 MB. https://doi.org/10.1016/j.microc.2013.03.009
Jacob, MS; Presti, DE. Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine. Med. Hypotheses, 1 Jan 2005, 64 (5), 930–937. 159 kB. https://doi.org/10.1016/j.mehy.2004.11.005
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, 1 Oct 2014, 231 (21), 4135-4144. 298 kB. https://doi.org/10.1007/s00213-014-3557-7
Dinger, J; Woods, C; Brandt, SD; Meyer, MR; Maurer, HH. Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol. Lett., 1 Jan 2016, 241, 82-94. 2.6 MB. https://doi.org/10.1016/j.toxlet.2015.11.013
Meyer, MR; Caspar, A; Brandt, SD; Maurer, HH. A qualitative/quantitative approach for the detection of 37 tryptamine-derived designer drugs, 5 β-carbolines, ibogaine, and yohimbine in human urine and plasma using standard urine screening and multi-analyte approaches. Anal. Bioanal. Chem., 1 Jan 2014, 406 (1), 225–237. 457 kB. https://doi.org/10.1007/s00216-013-7425-9 #DMT LC,MS
Taylor, EW; Nikam, S; Weck, B; Martin, A; Nelson, D. Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites. Life Sci., 19 Oct 1987, 41 (16), 1961–1969. 622 kB. https://doi.org/10.1016/0024-3205(87)90749-1
Fricke, J; Blei, F; Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int., 20 Aug 2017, 56 (40), 12352-12355. 1.8 MB. https://doi.org/10.1002/anie.201705489
Brandt, SD; Martins, CPB. Analytical methods for psychoactive N,N-dialkylated tryptamines. Trends Anal. Chem., 1 Sep 2010, 29 (8), 858–869. 446 kB. https://doi.org/10.1016/j.trac.2010.04.008 #1
Fricke, J; Sherwood, A; Kargbo, R; Orry, A; Blei, F; Naschberger, A; Rupp, B; Hoffmeister, D. Enzymatic route toward 6‐methylated baeocystin and psilocybin. ChemBioChem, 31 May 2019, 20 (22), 2824-2829. 3.2 MB. https://doi.org/10.1002/cbic.201900358 #5 NMR
Swanson, LR. Unifying theories of psychedelic drug effects. Front. Pharmacol., 2 Mar 2018, 9 (172). 1.7 MB. https://doi.org/10.3389/fphar.2018.00172
Baker, LE. Hallucinogens in drug discrimination. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 201-219. 342 kB. https://doi.org/10.1007/7854_2017_476
Zhang, S; Fan, Y; Shi, Z; Cheng, S. DFT-based QSAR and action mechanism of phenylalkylamine and tryptamine hallucinogens. Chin. J. Chem., 1 Apr 2011, 29 (4), 623–630. 166 kB. https://doi.org/10.1002/cjoc.201190132 #64
Clarke, EGC. The identification of some proscribed psychedelic drugs. J. Forensic Sci. Soc., 1 Jan 1967, 7 (1), 46-50. 336 kB. https://doi.org/10.1016/S0015-7368(67)70370-9 TLC
Buchanan, MS; Carroll, AR; Pass, D; Quinn, RJ. NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa. Magn. Reson. Chem., 1 Apr 2007, 45 (4), 359-361. 103 kB. https://doi.org/10.1002/mrc.1959 #3
Nichols, DE. Chemistry and structure–activity relationships of psychedelics. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #1
Nichols, DE. Psychedelics. Pharmacol. Rev., 1 Apr 2016, 68 (2), 264-355. 1.9 MB. https://doi.org/10.1124/pr.115.011478 Updated with published correction to Figure 4 (the α-methyl group was missing in the original)
Rickli, A; Moning, OD; Hoener, MC; Liechti, ME. Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens. Eur. Neuropsychopharmacol., 1 Aug 2016, 26 (8), 1327-1337. 845 kB. https://doi.org/10.1016/j.euroneuro.2016.05.001
Carbonaro, TM; Gatch, MB. Neuropharmacology of N,N-dimethyltryptamine. Brain Res. Bull., 1 Sep 2016, 126-1, 74-88. 813 kB. https://doi.org/10.1016/j.brainresbull.2016.04.016
Barrett, FS; Griffiths, RR. Classic hallucinogens and mystical experiences: Phenomenology and neural correlates. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 137-158. 848 kB. https://doi.org/10.1007/7854_2017_474
Lladó-Pelfort, L; Celada, P; Riga, MS; Troyano-Rodríguez,, E. Effect of hallucinogens on neuronal activity. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 75-105. 902 kB. https://doi.org/10.1007/7854_2017_473
McKenna, D; Riba, J. New world tryptamine hallucinogens and the neuroscience of ayahuasca. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2016; pp 283-311. 749 kB. https://doi.org/10.1007/7854_2016_472
Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466
Bogenschutz, MP; Ross, S. Therapeutic applications of classic hallucinogens. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 361-391. 360 kB. https://doi.org/10.1007/7854_2016_464
Burns, L; Roxburgh, A; Bruno, R; Van Buskirk, J. Monitoring drug markets in the Internet age and the evolution of drug monitoring systems in Australia. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 840-845. 113 kB. https://doi.org/10.1002/dta.1613
Chu, UB; Vorperian, SK; Satyshur, K; Eickstaedt, K; Cozzi, NV; Mavlyutov, T; Hajipour, AR; Ruoho, AE. Noncompetitive inhibition of indolethylamine-N-methyltransferase by N,N-dimethyltryptamine and N,N-dimethylaminopropyltryptamine. Biochemistry, 13 May 2014, 53 (18), 2956-2965. 3.4 MB. https://doi.org/10.1021/bi500175p #DMT NMR
Nichols, DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 1 Sep 2012, 1 (5), 559-579. 573 kB. https://doi.org/10.1002/wmts.42
Wang, Y; Chen, C. Synthesis of deuterium labeled tryptamine derivatives. J. Chin. Chem. Soc., 1 Oct 2007, 54 (5), 1363-1368. 92 kB. https://doi.org/10.1002/jccs.200700194 #8
Szára, S. DMT at fifty. Neuropsychopharmacol. Hung., 1 Dec 2007, 9 (4), 201–205. 446 kB.
Ly, C; Greb, AC; Cameron, LP; Wong, JM; Barragan, EV; Wilson, PC; Burbach, KF; Zarandi, SS; Sood, A; Paddy, MR; Duim, WC; Dennis, MY; McAllister, AK; Ori-McKenney, KM; Gray, JA; Olson, DE. Psychedelics promote structural and functional neural plasticity. Cell Rep., 1 Jun 2018, 23 (11), 3170–3182. 6.0 MB. https://doi.org/10.1016/j.celrep.2018.05.022 #DMT
Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 24 Apr 2003; pp 67–137. 6.3 MB.
Jacob, P; Shulgin, AT. Structure-activity relationships of the classic hallucinogens and their analogs. In Hallucinogens: An update. NIDA Research Monograph 146; Lin, GC; Glennon, RA, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1994; pp 74–91. 51 kB.
Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1 Jan 1982; Vol. 55 (3), pp 3–29. 928 kB. https://doi.org/10.1007/978-3-642-67770-0_1 #4a
Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., John Wiley & Sons, Inc., 1 Jan 1981; pp 1109–1137. 4.7 MB. #11
Glennon, RA; Jacyno, JM; Young, R; McKenney, JD; Nelson, D. Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines. J. Med. Chem., 1 Jan 1984, 27 (1), 41–45. 718 kB. https://doi.org/10.1021/jm00367a008 #1 NMR
Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1 Jan 1976; Vol. 4, pp 59–146. 3.1 MB. #XVII,XXVII
Barker, SA. N,N-dimethyltryptamine (DMT), an endogenous hallucinogen: Past, present, and future research to determine its role and function. Front. Neurosci., 6 Aug 2018, 12 (536). 1.0 MB. https://doi.org/10.3389/fnins.2018.00536 #DMT
Barker, SA. N,N-Dimethyltryptamine facts and myths. J. Psychopharmacol., 1 Jul 2018, 32 (7), 820–821. 63 kB. https://doi.org/10.1177/0269881118767648 #DMT
Nichols, DE. N,N-Dimethyltryptamine and the pineal gland: Separating fact from myth. J. Psychopharmacol., 1 Jan 2018, 32 (1), 30–36. 456 kB. https://doi.org/10.1177/0269881117736919 #DMT
Timmermann, C; Roseman, L; Williams, L; Erritzoe, D; Martial, C; Cassol, H; Laureys, S; Nutt, D; Carhart-Harris, R. DMT models the near-death experience. Front. Psychol., 15 Aug 2018, 9 (1424). 1.7 MB. https://doi.org/10.3389/fpsyg.2018.01424 #DMT
Dean, JG. Indolethylamine-N-methyltransferase polymorphisms: Genetic and biochemical approaches for study of endogenous N,N-dimethyltryptamine. Front. Neurosci., 23 Apr 2018, 12 (232). 2.1 MB. https://doi.org/10.3389/fnins.2018.00232 #N,N-dimethyltryptamine
Phipps, SM; Grundmann, O. Pharmacology and structure-activity relationship of natural products with psychoactive effects from Salvia divinorum, Mitragyna speciosa, and Ayahuasca. In Stud. Nat. Prod. Chem.; , Elsevier, 1 Jan 2017; pp 1–44. 1.4 MB. https://doi.org/10.1016/B978-0-444-63930-1.00001-6 #3
Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #DMT
Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, . 3.9 MB. #N,N-Dimethyltryptamine
Glennon, RA; Seggel, MR. Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. In Probing Bioactive Mechanisms; ACS Symposium Series; Magee, PS; Henry, DR; Block, JH, Eds., American Chemical Society, Washington, DC, 14 Nov 1989; Vol. 413, pp 264–280. 4.4 MB. https://doi.org/10.1021/bk-1989-0413.ch018 #28
Johnson, MW; Griffiths, RR; Hendricks, PS; Henningfield, JE. The abuse potential of medical psilocybin according to the 8 factors of the Controlled Substances Act. Neuropharmacology, 1 Nov 2018, 142, 143-166. 2.5 MB. https://doi.org/10.1016/j.neuropharm.2018.05.012 #DMT
Cameron, LP; Olson, DE. DARK classics in chemical neuroscience: N,N-Dimethyltryptamine (DMT). ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2344–2357. 1.4 MB. https://doi.org/10.1021/acschemneuro.8b00101 #1
Zamberlan, F; Sanz, C; Vivot, RM; Pallavicini, C; Erowid, F; Erowid, E; Tagliazucchi, E. The varieties of the psychedelic experience: A preliminary study of the association between the reported subjective effects and the binding affinity profiles of substituted phenethylamines and tryptamines. Front. Integr. Neurosci., 8 Nov 2018, 12 (54). 5.0 MB. https://doi.org/10.3389/fnint.2018.00054 #DMT
Geiger, HA; Wurst, MG; Daniels, RN. DARK classics in chemical neuroscience: Psilocybin. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2438–2447. 580 kB. https://doi.org/10.1021/acschemneuro.8b00186 #5
Chambers, SA; DeSousa, JM; Huseman, ED; Townsend, SD. The DARK side of total synthesis: Strategies and tactics in psychoactive drug production. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2307–2330. 8.1 MB. https://doi.org/10.1021/acschemneuro.7b00528 #168
Passie, T; Brandt, SD. Self-experiments with psychoactive substances: A historical perspective. In New Psychoactive Substances: Pharmacology, Clinical, Forensic and Analytical Toxicology; Maurer, HH; Brandt, SD, Eds., Springer, Berlin, Heidelberg, 1 Jan 2018; pp 69-110. 563 kB. https://doi.org/10.1007/164_2018_177 #DMT
Qu, S; Wang, G; Duan, W; Yao, S; Zuo, J; Tan, C; Zhu, D. Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus. Bioorg. Med. Chem., 15 May 2011, 19 (10), 3120–3127. 692 kB. https://doi.org/10.1016/j.bmc.2011.04.004 #2a MS,NMR
Shulgin, AT; Nichols, DE. Characterization of three new psychotomimetics. In The Psychopharmacology of Hallucinogens; Stillman, RC; Willette, RE, Eds., Pergamon, 1 Jan 1978; pp 74–83. 210 kB. https://doi.org/10.1016/B978-0-08-021938-7.50010-2 #8 A different layout of the same paper
Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S2 Tryptamines DMT
Glennon, RA; Schubert, E; Jacyno, JM; Rosecrans, JA. Studies on several 7-substituted N,N-dimethyltryptamines. J. Med. Chem., 1 Nov 1980, 23 (11), 1222–1226. 711 kB. https://doi.org/10.1021/jm00185a014 #2 NMR
Glennon, RA; Young, R; Rosecrans, JA; Kallman, MJ. Hallucinogenic agents as discriminative stimuli: A correlation with serotonin receptor affinities. Psychopharmacology, 1 May 1980, 68 (2), 155–158. 395 kB. https://doi.org/10.1007/BF00432133 #DMT
Glennon, RA; Liebowitz, SM; Mack, EC. Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogs. J. Med. Chem., 1 Aug 1978, 21 (8), 822–825. 597 kB. https://doi.org/10.1021/jm00206a022 #1
Fricke, J; Lenz, C; Wick, J; Blei, F; Hoffmeister, D. Production options for psilocybin: Making of the magic. Chem. Eur. J., 18 Jan 2019, 25 (4), 897–903. 1.8 MB. https://doi.org/10.1002/chem.201802758 #10
Heim, R. Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. SC. D. Thesis, Freie Universität, Berlin, 1 Jan 2004. 3.9 MB. #9 In German. MS,NMR,IR
McCorvy, JD. Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics. Ph. D. Thesis, Purdue University, 1 Jan 2012. 3.9 MB. #DMT
Uthaug, MV; Lancelotta, R; van Oorsouw, K; Kuypers, KPC; Mason, N; Rak, J; Šuláková, A; Jurok, R; Maryška, M; Kuchař, M; Páleníček, T; Riba, J; Ramaekers, JG. A single inhalation of vapor from dried toad secretion containing 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in a naturalistic setting is related to sustained enhancement of satisfaction with life, mindfulness-related capacities, and a decrement of psychopathological symptoms. Psychopharmacology, 13 Apr 2019, 236 (9), 2653-2666. 1.0 MB. https://doi.org/10.1007/s00213-019-05236-w #DMT
Yasuoka, T; Muroi, H; Okazaki, R; Matsumoto, Y; Terauchi, Y; Sasatani, T. Analysis of tryptamine group compounds. JCCL, 1 Jan 2003, (43), 63–69. 151 kB. #DMT Japanese, English abstract LC,MS,NMR,IR,UV
Kang, S; Johnson, CL; Green, JP. Theoretical studies on the conformations of psilocin and mescaline. Mol. Pharmacol., 1 Sep 1973, 9 (5), 640–648. 6.9 MB. #N,N-dimethyltryptamine other
Halberstadt, AL; Chatha, M; Klein, AK; Wallach, J; Brandt, SD. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology, 1 May 2020, 167, 107933. 2.4 MB. https://doi.org/10.1016/j.neuropharm.2019.107933 #DMT
Sexton, JD; Nichols, CD; Hendricks, PS. Population survey data informing the therapeutic potential of classic and novel phenethylamine, tryptamine, and lysergamide psychedelics. Front. Psychiatry, 11 Feb 2020, 10 (896). 529 kB. https://doi.org/10.3389/fpsyt.2019.00896 #DMT
Poulie, CBM; Jensen, AA; Halberstadt, AL; Kristensen, JL. DARK Classics in Chemical Neuroscience: NBOMes. ACS Chem. Neurosci., 2 Dec 2020, 11 (23), 3860-3869. 860 kB. https://doi.org/10.1021/acschemneuro.9b00528 #DMT
Sadzot, B; Baraban, JM; Glennon, RA; Lyon, RA; Leonhardt, S; Jan, C; Titeler, M. Hallucinogenic drug interactions at human brain 5-HT2 receptors: implications for treating LSD-induced hallucinogenesis. Psychopharmacology, 1 Aug 1989, 98 (4), 495–499. 895 kB. https://doi.org/10.1007/BF00441948 #DMT
Dunlap, LE; Azinfar, A; Ly, C; Cameron, LP; Viswanathan, J; Tombari, RJ; Myers-Turnbull, D; Taylor, JC; Grodzki, AC; Lein, PJ; Kokel, D; Olson, DE. Identification of psychoplastogenic N,N-dimethylaminoisotryptamine (isoDMT) analogues through structure–activity relationship studies. J. Med. Chem., 13 Feb 2020, 63 (3), 1142–1155. 12.7 MB. https://doi.org/10.1021/acs.jmedchem.9b01404 #1 MS,NMR,IR,TLC
Olson, DE. Psychoplastogens: A promising class of plasticity-promoting neurotherapeutics. J. Exp. Neurosci., 1 Jan 2018, 12 (2018). 204 kB. https://doi.org/10.1177/1179069518800508 #DMT
Barlow, RB; Khan, I. Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations. Br. J. Pharmacol., 1 Mar 1959, 14 (1), 99–107. 1.9 MB. https://doi.org/10.1111/j.1476-5381.1959.tb00934.x #1 other
Fenderson5555. Mechanisms in DMT synthesis. , 3 Jan 2011. . Fenderson5555 2.6 MB.
Fenderson5555. Shulgin DMT synthesis. , 14 Dec 2016. . Fenderson5555 2.5 MB. #DMT
Cozzi, NV; Daley, PF. Synthesis and characterization of high-purity N,N-dimethyltryptamine hemifumarate for human clinical trials. Drug Test. Anal., 14 Jul 2020, 12 (10), 1483–1493. 3.5 MB. https://doi.org/10.1002/dta.2889 #DMT GC,LC,MS,NMR,other
Flanagan, TW; Billac, GB; Landry, AN; Sebastian, MN; Cormier, SA; Nichols, CD. Structure–activity relationship analysis of psychedelics in a rat model of asthma reveals the anti-inflammatory pharmacophore. ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 488-502. 13.3 MB. https://doi.org/10.1021/acsptsci.0c00063 #DMT
Sherwood, AM; Claveau, R; Lancelotta, R; Kaylo, KW; Lenoch, K. Synthesis and characterization of 5-MeO-DMT succinate for clinical use. ACS Omega, 15 Dec 2020, 5 (49), 32067–32075. 3.2 MB. https://doi.org/10.1021/acsomega.0c05099 #2 MS,NMR
Folen, VA. X-Ray powder diffraction data for some drugs, excipients, and adulterants in illicit samples. J. Forensic Sci., 1 Apr 1975, 20 (2), 348–372. 502 kB. https://doi.org/10.1520/JFS10282J #27 other
Åstrand, A; Guerrieri, D; Vikingsson, S; Kronstrand, R; Green, H. In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors—On-target receptor potency and efficacy, and off-target effects. Forensic Sci. Int., 1 Dec 2020, 317, 110553. 1.7 MB. https://doi.org/10.1016/j.forsciint.2020.110553 #N,N-dimethyltryptamine (DMT)
Laing, RR. The disposition of Nicholas Sand’s conspiracy to traffic in LSD, MDA, MDMA and DMT charges. JCLIC, 1 Jul 1998, 8 (3), 15-16. 575 kB.
Chappell, JS. Infrared absorption properties of solid-dosage drug substances. Part I. Mechanism of infrared absorption. JCLIC, 1 Oct 2012, 22 (4), 8-26. 1.3 MB. IR
Adelaars, A. Court case in Holland against the use of ayahuasca by the Dutch Santo Daime church. JCLIC, 1 Jul 2001, 11 (3), 12-13. 514 kB.
Adelaars, A. Freedom of religion versus the psychotropic substance treaty: Notes on the ayahuasca court case in Holland. JCLIC, 1 Mar 2001, 11 (2), 3-5. 521 kB.
Nichols, DE; Walter, H. The history of psychedelics in psychiatry. Pharmacopsychiatry, 1 Jul 2021, 54 (04), 151–166. 305 kB. https://doi.org/10.1055/a-1310-3990 #DMT
Kozlowska, U; Nichols, C; Wiatr, K; Figiel, M. From psychiatry to neurology: Psychedelics as prospective therapeutics for neurodegenerative disorders. J. Neurochem., 13 Sep 2021, 95 (6), 1575-1584. 35.4 MB. https://doi.org/10.1111/jnc.15509 #DMT
Dong, C; Ly, C; Dunlap, LE; Vargas, MV; Sun, J; Hwang, I; Azinfar, A; Oh, WC; Wetsel, WC; Olson, DE; Tian, L. Psychedelic-inspired drug discovery using an engineered biosensor. Cell, 13 May 2021, 184 (10), 2779-2792.e18. 8.3 MB. https://doi.org/10.1016/j.cell.2021.03.043 #DMT NMR
Cumming, P; Scheidegger, M; Dornbierer, D; Palner, M; Quednow, BB; Martin-Soelch, C. Molecular and functional imaging studies of psychedelic drug action in animals and humans. Molecules, 1 Jan 2021, 26 (9), 2451. 3.5 MB. https://doi.org/10.3390/molecules26092451 #9
Mesley, RJ; Evans, WH. Infrared identification of some hallucinogenic derivatives of tryptamine and amphetamine. J. Pharm. Pharmacol., 1 May 1970, 22 (5), 321–332. 775 kB. https://doi.org/10.1111/j.2042-7158.1970.tb08533.x #N,N-Dimethyltryptamine IR
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #4.7
Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #DMT
Shulgin, AT. Psychotomimetic agents related to the catecholamines. J. Psychedelic Drugs, 1 Apr 1969, 2 (2), 14–19. 782 kB. https://doi.org/10.1080/02791072.1969.10524409 #VIIa
Agurell, S; Nilsson, JLG. Biosynthesis of psilocybin. Part II. Incorporation of labelled tryptamine derivatives. Acta Chem. Scand., 1 Jan 1968, 22 (4), 1210–1218. 805 kB. https://doi.org/10.3891/acta.chem.scand.22-1210 #XII
Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8.6 MB. #DMT
Vogel, WH; Evans, BD. Structure-activity-relationships of certain hallucinogenic substances based on brain levels. Life Sci., 15 May 1977, 20 (10), 1629–1635. 419 kB. https://doi.org/10.1016/0024-3205(77)90335-6 #Dimethyl-T (DMT)
Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 4.8 MB. https://doi.org/10.1080/02791072.1979.10472093
Glennon, RA; Rosecrans, JA. Indolealkylamine and phenalkylamine hallucinogens: A brief overview. Neurosci. Biobehav. Rev., 1 Jan 1982, 6 (4), 489–497. 895 kB. https://doi.org/10.1016/0149-7634(82)90030-6 #3a
Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #81
McKenna, DJ; Towers, HHN. Biochemistry and pharmacology of tryptamines and beta-carbolines: A minireview. J. Psychoactive Drugs, 1 Jan 1984, 16 (4), 347–358. 10.8 MB. https://doi.org/10.1080/02791072.1984.10472305 #DMT
Mckenna, DJ; Towers, GHN; Abbott, FS. Monoamine oxidase inhibitors in South American hallucinogenic plants part 2: Constituents of orally-active Myristicaceous hallucinogens. J. Ethnopharmacol., 1 Nov 1984, 12 (2), 179–211. 2.5 MB. https://doi.org/10.1016/0378-8741(84)90048-5 #DMT GC,MS,UV