- 5-MeO-T
- 5-Methoxytryptamine
- 5MT
- Mexamine
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-T
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-OMeT
Glennon, RA; Chaurasia, C; Titeler, M. Binding of indolylalkylamines at 5-HT2 serotonin receptors: Examination of a hydrophobic binding region J. Med. Chem., 1 Jan 1990, 33 (10), 2777–2784. 1.2 MB. https://doi.org/10.1021/jm00172a016 #6 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 #2
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
Nichols, DE; Lloyd, DH; Johnson, MP; Hoffman, AJ. Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors J. Med. Chem., 1 Jul 1988, 31 (7), 1406–1412. 1.1 MB. https://doi.org/10.1021/jm00402a026 NMR
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
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 #5 MS,NMR
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. #357, 358 Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols. LC,MS,NMR,IR,UV,TLC,spot
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 #S14
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 LC,MS
Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin) Ann. N. Y. Acad. Sci., 1 Jan 1962, 96 (1), 142–151. 458 kB. https://doi.org/10.1111/j.1749-6632.1962.tb50109.x
Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2.2 MB. #26 In German. MS,NMR
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 #25
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
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 #T29 NMR
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 #T29 NMR
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
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
Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT2A-Rezeptors aus der Klasse Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #39 LC,MS,NMR,IR
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
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.
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 #5MeO-T GC,LC,MS,UV
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 #1b NMR
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. #2 In German. MS,NMR,IR
Rothchild, R. Proton and carbon‐13 NMR studies of some tryptamines, precursors, and derivatives: Ab initio calculations for optimized structures Spectrosc. Lett., 1 Jan 2005, 38 (4–5), 521–537. 324 kB. https://doi.org/10.1081/SL-200062932 #1 NMR
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-T
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 #7 MS,NMR
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-Methoxytryptamine IR
Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #Table 8.2
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-T
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 #1b
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 #94
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-tryptamine 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 #23 NMR,IR
Klein, MT; Dukat, M; Glennon, RA; Teitler, M. Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: A comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships J. Pharmacol. Exp. Ther., 1 Jun 2011, 337 (3), 860–867. 1.7 MB. https://doi.org/10.1124/jpet.111.179606 #3
Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #11, 51
Chen, X; Li, J; Yu, L; Dhananjaya, D; Maule, F; Cook, S; Chang, L; Gallant, J; Press, D; Bains, JS; Raithatha, S; Hagel, J; Facchini, P. Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery ResearchSquare, 10 Mar 2023, n/a. 7.7 MB. https://doi.org/10.21203/rs.3.rs-2667175/v1 #5-Methoxytryptamine MS,NMR