Explore 5-MeO-DMT | TiHKAL

TiHKAL book II entry 5-MeO-DMT

ChemSpider 1766
PubChem 1832
Wikidata Q570757
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Wikipedia 5-MeO-DMT
Blotter 5-MeO-DMT (freebase)
Blotter 5-MeO-DMT (oxalate)
Blotter 5-MeO-DMT
PsychonautWiki 5-MeO-DMT
Trout’s Notes 5-Methoxy-N,N-dimethyltryptamine. In Some Simple Tryptamines, 2nd ed., pp. 121–135
Project Response 5-MeO-N,N-DMT (610-06A)
bluelight.org The Big & Dandy 5-MeO-DMT Thread Part 1
bluelight.org The Big & Dandy 5-MeO-DMT Thread Part 2
bluelight.org 5-MeO-DMT Scraps
Rhodium Shulgin & Nichols: Three new psychotomimetics: para-DOT - MDMA - α,O-DMS
Rhodium Psychedelic chemistry by M. V. Smith, chapter 3
bluelight.org 5-MeO-DMT Effects and Ratings Survey Results
aipsin.com 5-MeO-DMT (Iss. 8, Aug 2020: X-79)
aipsin.com 5-MeO-DMT (Iss. 10, Oct 2020: X-88)

TiHKAL #6 DMT · #7 2,α-DMT · #10 EIPT · #13 Harmaline · #19 5-HO-DMT · #31 5,6-MDO-DMT · #35 Melatonin · #36 5-MeO-DET · #39 4-MeO-MIPT · #40 5-MeO-MIPT · #42 5-MeO-NMT · #43 5-MeO-pyr-T · #45 5-MeO-TMT · #46 5-MeS-DMT · #50 NMT

Phenethylamine: Von der Strucktur zur Funktion 5-MeO-DMT: 7.3 (34) 491, 503 · 8.5 (432) 864

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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

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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

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

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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

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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

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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

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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

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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

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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

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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-HT_2A 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-HT_2A 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

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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

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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

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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

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4-HO-MET · 4-Hydroxy-N-methyl-N-ethyltryptamine

5-MeO-α,N-DMT · 5-MeO-α-methyl-NMT · 5-Methoxy-α-methyl-N-methyltryptamine · α,N,O-TMS

1-MeO-DMT · 1-Methoxy-N,N-dimethyltryptamine

1-Methyl-4-HO-DMT · 1-Methyl-4-hydroxy-N,N-dimethyltryptamine · 1-Methylpsilocin · CMY

5-MeO-AET · 5-Methoxy-α-ethyltryptamine

4-MeO-DMT · 4-Methoxy-N,N-dimethyltryptamine · PSOM

6-MeO-DMT · 6-Methoxy-N,N-dimethyltryptamine

7-MeO-DMT · 7-Methoxy-N,N-dimethyltryptamine

5-HO-TMT⁺ · 5-HTQ · 5-Hydroxy-N,N,N-trimethyltryptamine⁺

5-MeO-NET · 5-Methoxy-N-ethyltryptamine

2-Methyl-4-HO-DMT · 2-Methyl-4-hydroxy-N,N-dimethyltryptamine · 2-Methylpsilocin

4-HO-α-methyl-DMT · 4-Hydroxy-α-methyl-N,N-dimethyltryptamine · α-Methylpsilocin

4-HO-DMHT

1-Methyl-5-HO-DMT · 1-Methyl-5-hydroxy-N,N-dimethyltryptamine · 1-Methylbufotenine

5-PrO-T · 5-Propoxytryptamine

5-IPrO-T · 5-Isopropoxytryptamine

5-EtO-NMT · 5-Ethoxy-N-methyltryptamine

10611

5-HO-NIPT · 5-Hydroxy-N-isopropyltryptamine

6-MeO-iso-DMT · 6-Methoxy-N,N-dimethyl-isotryptamine

5-MeO-iso-DMT · 5-Methoxy-N,N-dimethyl-isotryptamine

4-Isobutylaminorex

4-tert-Butylaminorex

4-Methyl-5-HO-DMT · 4-Methyl-5-hydroxy-N,N-dimethyltryptamine · 4-Methylbufotenin

Acetyl-norfentanyl

Ritalinamide · Ritalinic acid amide

4-HO-NIPT · 4-Hydroxy-N-isopropyltryptamine

5-EtO-AMT · 5-Ethoxy-α-methyltryptamine

7-MeO-iso-DMT · 7-Methoxy-N,N-dimethyl-isotryptamine

4-MeO-iso-DMT · 4-Methoxy-N,N-dimethyl-isotryptamine

4-HO-TMT⁺ · 4-Hydroxy-N,N,N-trimethyltryptamine⁺ · Dephosphorylated aeruginascin

7-Methyl-4-HO-DMT · 7-Methyl-4-hydroxy-N,N-dimethyltryptamine · 7-Methylpsilocin

5-Methyl-4-HO-DMT · 5-Methyl-4-hydroxy-N,N-dimethyltryptamine · 5-Methylpsilocin

p1-194: 5-MeO-DMT; ALEPH-2: Trials
p1-195: 5-MeO-DMT
p2-298: 5-MeO-DMT
p2-323.3: Experiment for Death valley