- 5-MeO-DMT
- 5-Methoxy-N,N-dimethyltryptamine
- Bufotenine methyl ether
- Indole, 5-methoxy-3-[2-(dimethylamino)ethyl]
- 5-Methoxy-3-[2-(dimethylamino)ethyl]indole
- O-Methylbufotenine
- OMB
- N,N,O-TMS
- N,N,O-Trimethylserotonin
- Tryptamine, 5-methoxy-N,N-dimethyl
Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8.4 MB. #5-MeO-DMT
Callaway, JC; Grob, CS; McKenna, DJ; Nichols, DE; Shulgin, AT; Tupper, KW; Sklerov, JH; Levine, B; Moore, KA. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-Dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation. J. Anal. Toxicol., 1 Jul 2006, 30 (6), 406–407. 53 kB. https://doi.org/10.1093/jat/30.6.406
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
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
Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. https://doi.org/10.1016/0024-3205(68)90200-2 #5MeO-DMT
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 #5-OMe DMT
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
Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. https://doi.org/10.1016/0024-3205(91)90582-V
Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. https://doi.org/10.1016/S0091-3057(99)00178-1
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
Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1.9 MB. https://doi.org/10.1021/jm00098a005 MS,NMR,IR
Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. https://doi.org/10.1021/jm00399a031 #3
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 #9a MS
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
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 #6
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 #3
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
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 #9a MS,NMR
Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. https://doi.org/10.1021/jm950498t #17 MS,NMR
Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. https://doi.org/10.1021/jm00350a005 #4 NMR,IR
Halberstadt, AL; Nichols, DE; Geyer, MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology, 1 Jun 2012, 221 (4), 709–218. 296 kB. https://doi.org/10.1007/s00213-011-2616-6
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
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. #15 Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols. LC,MS,NMR,IR,UV,TLC,spot
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
Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. https://doi.org/10.1021/jm990550b #11 NMR
Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 1 Jan 2008, 54 (1), 89–96. 1.9 MB. https://doi.org/10.1248/jhs.54.89
Shen, H; Jiang, X; Winter, JC; Yu, A. Psychedelic 5-methoxy-N,N-dimethyltryptamine: Metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr. Drug Metab., 1 Oct 2010, 11 (8), 659–666. 319 kB. https://doi.org/10.2174/138920010794233495
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
Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB. GC,LC,MS,NMR,IR,spot
Benington, F; Morin, RD; Clark, LC. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem., 1 Dec 1958, 23 (12), 1977–1979. 401 kB. https://doi.org/10.1021/jo01106a046 #XII
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
Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. https://doi.org/10.1016/0014-2999(81)90106-0 #5-MeO-DMT
Schmid, CL; Bohn, LM. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci., 6 Oct 2010, 30 (40), 13513–13524. 1.5 MB. https://doi.org/10.1523/JNEUROSCI.1665-10.2010
Glennon, RA; Titeler, M; McKenney, JD. Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci., 17 Dec 1984, 35 (25), 2505–2511. 332 kB. https://doi.org/10.1016/0024-3205(84)90436-3 #16
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 #25
Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Mar 2018, 3 (1). 1.2 MB. https://doi.org/10.16889/isomerdesign-5
Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Mar 2018, 3 (1). 5.7 MB. https://doi.org/10.16889/isomerdesign-5-supp
Morris, H. Bufo: The psychedelic toad. Hamilton’s Pharmacopeia, 28 Nov 2017. S2 E01, 39:55. Vice 115.1 MB.
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
Collins, M. Some new psychoactive substances: Precursor chemical and synthesis-driver end-products. Drug Test. Anal., 1 Jul 2001, 3 (7–8), 404–416. 178 kB. https://doi.org/10.1002/dta.315
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 #2
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
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
May, JA; Chen, H; Rusinko, A; Lynch, VM; Sharif, NA; McLaughlin, MA. A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole. J. Med. Chem., 1 Sep 2003, 46 (19), 4188–2195. 126 kB. https://doi.org/10.1021/jm030205t #1a MS,NMR
May, JA; Dantanarayana, AP; Zinke, PW; McLaughlin, MA; Sharif, NA. 1-((S)-2-Aminopropyl)-1H-indazol-6-ol: A potent peripherally acting 5-HT2 receptor agonist with ocular hypotensive activity. J. Med. Chem., 12 Jan 2006, 49 (1), 318–328. 124 kB. https://doi.org/10.1021/jm050663x #18
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 #4l
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. #5
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 #10 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. #XIX
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 #5-MeO-DMT
Taschwer, M; Ebner, E; Schmid, MG. Test purchase of new synthetic tryptamines via the Internet: Identity check by GC-MS and separation by HPLC. J. Appl. Pharm. Sci., 1 Jan 2016, 6 (1), 028–034. 504 kB. https://doi.org/10.7324/JAPS.2016.600105
Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #5-MeO-DMT
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 #5-Methoxy-DMT
Chapman, SJ. Novel Psychoactive Spectra: NMR of (mostly) Novel Psychoactive Substances. BLOTTER, 25 Jun 2018, 3 (2). https://doi.org/10.16889/isomerdesign-6 #5-MeO-DMT (oxalate) NMR
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 #5-MeO-DMT
Tsujikawa, K; Mohri, H; Kuwayama, K; Miyaguchi, H; Iwata, YT; Gohda, A; Fukushima, S; Inoue, H; Kishi, T. Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. Forensic Sci. Int., 1 Jan 2006, 164 (2–3), 172–178. 634 kB. https://doi.org/10.1016/j.forsciint.2006.01.004 #5-MeO-DMT
Seto, T; Takahashi, M; Nagashima, M; Suzuki, J; Yasuda, I. The identifications and the aspects of the commercially available uncontrolled drugs purchased between Apr. 2003 and Mar. 2004. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 75–80. 1.2 MB. #5-MeO-DMT MS,NMR,UV
May, JA; Sharif, NA; Chen, H; Liao, JC; Kelly, CR; Glennon, RA; Young, R; Li, J; Rice, KC; France, CP. Pharmacological properties and discriminative stimulus effects of a novel and selective 5-HT2 receptor agonist AL-38022A [(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine]. Pharmacol. Biochem. Behav., 1 Jan 2009, 91 (3), 307–314. 476 kB. https://doi.org/10.1016/j.pbb.2008.07.015 #5-OMe-DMT
Barsuglia, JP; Polanco, M; Palmer, R; Malcolm, BJ; Kelmendi, B; Calvey, T. A case report SPECT study and theoretical rationale for the sequential administration of ibogaine and 5-MeO-DMT in the treatment of alcohol use disorder. In Progress in Brain Research; , Elsevier, 25 Oct 2018; . 1.4 MB. https://doi.org/10.1016/bs.pbr.2018.08.002 #5-MeO-DMT
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 #5-MeO-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 #11
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 #10 A different layout of the same paper
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 #3 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 #5-OMe 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 #2
Glennon, RA; Rosecrans, JA; Young, R; Gaines, J. Hallucinogens as a discriminative stimuli: Generalization of DOM to a 5-methoxy-N,N-dimethyltryptamine stimulus. Life Sci., 12 Mar 1979, 24 (11), 993–997. 261 kB. https://doi.org/10.1016/0024-3205(79)90317-5 #5-OMe DMT
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. #10 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. #5-MeO-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 #5-MeO-DMT
Kazushi, M; Kaori, S; Masashi, S; Yoshitsugu, M; Tsutomu, K. Analysis of tryptamines designated newly as narcotics. JCCL, 1 Jan 2005, (45), 77–87. 565 kB. #5-MeO-DMT Japanese, English abstract LC,MS,NMR,IR,UV
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. #5-MeO-DMT Japanese, English abstract LC,MS,NMR,IR,UV
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 #5-MeO-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 #5-OMe-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 #28 MS,NMR,IR,TLC
Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE. Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J. Med. Chem., 1 Nov 2000, 43 (24), 4701–4710. 494 kB. https://doi.org/10.1021/jm000339w #2c MS,NMR
Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #5-MeO-DMT
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 #5-MeO-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 #6 MS,NMR
Olson, DE. The subjective effects of psychedelics may not be necessary for their enduring therapeutic effects. ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 563-567. 795 kB. https://doi.org/10.1021/acsptsci.0c00192 #5-MeO-DMT
Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds. Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #5-methoxy-N,N-dimethyltryptamine
Cameron, LP; Tombari, RJ; Lu, J; Pell, AJ; Hurley, ZQ; Ehinger, Y; Olson, DE. A non-hallucinogenic psychedelic analogue with therapeutic potential. Nature, 1 Jan 2021, 589 (7842), 474–479. 10.5 MB. https://doi.org/10.1038/s41586-020-3008-z #5-MeO-DMT MS,NMR,IR
Nakagawasai, O; Arai, Y; Satoh, S; Satoh, N; Neda, M; Hozumi, M; Oka, R; Hiraga, H; Tadano, T. Monoamine oxidase and head-twitch response in mice: Mechanisms of α-methylated substrate derivatives. Neurotoxicology, 1 Jan 2004, 25 (1), 223–232. 169 kB. https://doi.org/10.1016/S0161-813X(03)00101-3 #5-MeODMT
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 #5-MeO-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 #5-MeO 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 #15, 47
Kikura-Hanajiri, R; Kawamura, M; Uchiyama, N; Ogata, J; Kamakura, H; Saisho, K; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part I: GC-MS and LC-MS. Yakugaku Zasshi, 1 Jun 2008, 128 (6), 971–979. 1.4 MB. https://doi.org/10.1248/yakushi.128.971 #5-MeO-DMT Incorrect structures drawn. Corrected structures in errata page at end. GC,LC,MS,UV
Uchiyama, N; Kawamura, M; Kamakura, H; Kikura-Hanajiri, R; Goda, Y. Analytical data of designated substances (shitei-yakubutsu) controlled by the pharmaceutical affairs law in Japan, Part II: Color test and TLC. Yakugaku Zasshi, 1 Jan 2008, 128 (6), 981–987. 406 kB. https://doi.org/10.1248/yakushi.128.981 #5-MeO-DMT TLC
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 #5-Methoxy-N,N-dimethyltryptamine IR
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #4.23
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 #5-MeO-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 #5-Methoxy-DMT
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 #3e
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 #82
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 #5MeO-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 #5-MeO-DMT GC,MS,UV
Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1.1 MB. https://doi.org/10.1021/jm00039a004 #25 NMR,IR
McBride, MC. Bufotenine: Toward an understanding of possible psychoactive mechanisms. J. Psychoactive Drugs, 1 Jan 2000, 32 (3), 321–331. 1.6 MB. https://doi.org/10.1080/02791072.2000.10400456
Kurrasch-Orbaugh, DM. Elucidation of the serotonin 5-HT2A receptor-coupled phospholipase A2 signaling pathway. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 May 2002. 7.9 MB. #5MeO-DMT
Zimmerman, MM. The identification of 5-methoxy-alpha-methyltryptamine (5-MeO-AMT). Microgram J., 1 Jul 2003, 1 (3–4), 158–162. 269 kB. MS