置換トリプタミン

置換トリプタミン、または単にトリプタミンは、セロトニン類似体（すなわち、5-ヒドロキシトリプタミン類似体）としても知られ、トリプタミン自体から誘導されたと考えられる有機化合物です。すべてのトリプタミンの分子構造は、アミノ基（NH₂ _）にエチル基（−CH₂–CH₂−）側鎖を介して結合したインドール環系を含んでいます。置換トリプタミンでは、インドール環、側鎖、および／またはアミノ基が、水素原子（H）の1つを別の基に置換することによって修飾されています。

よく知られているトリプタミンには、重要な神経伝達物質であるセロトニンや、睡眠覚醒サイクルの調節に関わるホルモンであるメラトニンなどがあります。トリプタミンアルカロイドは、菌類、植物、動物に存在し、時にはその物質の神経学的または精神作用のために人間によって使用されます。トリプタミンアルカロイドの代表的な例としては、シロシビン（「シロシビンキノコ」由来）やDMTなどがあります。南米では、ジメチルトリプタミンはチャクルナなどの多くの植物源から得られ、アヤワスカの醸造によく使用されます。また、片頭痛薬のスマトリプタンや幻覚剤など、多くの合成トリプタミンも作られています。2022年の研究では、野生キノコに含まれるトリプタミンの種類が治療効果に影響を与える可能性があることがわかっています。^[¹^]

トリプタミン構造、特にそのインドール環は、LSD、イボガイン、ハルマリン、ミトラギニン、ヨヒンビンなどの環状トリプタミンなどのより複雑な化合物の構造の一部である可能性がある。数十種類のトリプタミン化合物の徹底的な調査は、 1997年にアレクサンダー・シュルギンとアン・シュルギンによってTiHKAL（私が知っていて愛したトリプタミン）というタイトルで出版された。^[²^]

使用と効果

幻覚性トリプタミンの投与量、効力、持続時間、および効果については、 Alexander Shulginや他の著者によってレビューされています。 ^{[ 3 ]}^{[ 4 ]}^{[ 5 ]}^{[ 6 ]}^{[ 2 ]}^{[ 7 ]}^{[ 8 ]}^{[ 9 ]}^{[ 10 ]}^{[ 11 ]}

環非置換トリプタミン

4-ヒドロキシトリプタミン

5-ヒドロキシトリプタミン

5-メトキシトリプタミン

α-アルキルトリプタミン

その他のトリプタミン類

相互作用

薬理学

薬力学

化学

合成

アレクサンダー・シュルギンは著書『TiHKAL（私が知っていて愛したトリプタミン）』で、数多くのトリプタミンの化学合成について述べている。[ ²^]^{トリプタミン}を合成するためのよく知られ、広く用いられている合成法は、インドールから始まるスピーター・アンソニー法である。^[³⁸^]^[³⁹^]^[⁴⁰^]トリプタミンではなくインドールから始まるなど、他のトリプタミン合成法も報告されている。 ^[³⁸^]^[³⁹^]幻覚性トリプタミンであるブフォテニン（5-HO-DMT）と5-MeO-DMT （メブフォテニン）の化学合成については、包括的にレビューされている。^[⁴¹^]

置換トリプタミン類のリスト

List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.^[85]^[86]^[87] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.^[87] This is analogous to α-methylation of phenethylamine into amphetamine.^[87]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,^[88]^[89]^[90]^[91] and produce psychostimulant, entactogen, and/or psychedelic effects.^[85]^[86]^[87] The most well-known of these agents are α-methyltryptamine (AMT) and α-ethyltryptamine (AET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.^[86]^[87] In accordance with its action as a dual releasing agent of serotonin and dopamine, AET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as AMT, 5-MeO-AMT, and various others.^[92]

List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known.^[97]^[99]^[102] These compounds are α-alkyl-β-ketotryptamines and are analogous to the cathinones (β-ketoamphetamines) of the related phenethylamine family. Known β-ketotryptamines include BK-NM-AMT, BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT.^[97]^[99]^[102] They act as monoamine releasing agents.^[97]^[99]^[102]

Cyclized tryptamines

Examples of cyclized tryptamines include:

β-Carbolines such as harmala alkaloids like harmaline
Ibogalogs (hexahydroazepinoindoles) such as ibogainalog, tabernanthalog, PNU-22394, and PHA-57378
Iboga alkaloids like ibogaine, noribogaine, ibogamine, and tabernanthine
Ergolines and lysergamides such as lysergic acid diethylamide (LSD) and ergot alkaloids like ergine (lysergic acid amide; LSA)
Partial ergolines and lysergamides like RU-27849, FHATHBIN, NDTDI, and CT-5252
Mitragyna alkaloids such as mitragynine
Yohimbans such as Rauvolfia and Corynanthealkaloids like yohimbine and rauwolscine
Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, and L-760790
Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, eletriptan, and MSP-2020
Imidazolylindoles like AGH-107, AGH-192, and AH-494
Piperidinylethylindoles like pip-T, 5-MeO-pip-T, and indoramin
Morpholinylethylindoles like mor-T and 5-MeO-mor-T
Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI
Pertines (phenylpiperazinylethylindoles) like alpertine, milipertine, oxypertine, and solypertine
Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban
Tetrahydropyrroloquinolines like bufothionine, O-methylnordehydrobufotenine, and dehydrobufotenine
Others like 5-MeO-IsoqT, barettin, cyclic 3-hydroxymelatonin, metralindole, and Z5247692566

Other closely related cyclized tryptamine-like compounds include the following:

Piperidinylindoles like SN-22, BRL-54443, naratriptan, LY-334370, and sertindole
Tetrahydropyridinylindoles like RU-24969, EMD-386088, and LY-367,265
Tetrahydropyridinylindazoles like VU6067416
Tetrahydropyridinylpyrrolopyridines like (R)-69, (R)-70, CP-93129, and CP-94253
Pyridopyrroloquinoxalines (tetracyclic γ-carbolines) like lumateperone, IHCH-7113, IHCH-7086, and ITI-1549

Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped (isotryptamines) and/or replaced with related cores such as indene, indoline, indazole, indolizine, benzothiophene, or benzofuran. Like tryptamines, these related compounds are primarily active as agonists at the 5-HT₂ family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches, or as anorectics.

Overview table

References

↑Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.
1 2 3 4 5 6 7 8 9Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
1 2 3 4 5 6 7Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs"(PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original(PDF) on August 5, 2023.
1 2 3 4 5 6 7Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
↑Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
↑Alexander T. Shulgin (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
1 2 3 4 5Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881.
1 2 3 4 5Halberstadt, Adam L.; Chatha, Muhammad; Klein, Adam K.; Wallach, Jason; Brandt, Simon D. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species"(PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Archived from the original(PDF) on 26 March 2025. Table 4 Human potency data for selected hallucinogens. [...]
1 2 3 4 5Ballentine, Galen; Friedman, Samuel Freesun; Bzdok, Danilo (March 2022). "Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences". Sci Adv. 8 (11) eabl6989. Bibcode:2022SciA....8L6989B. doi:10.1126/sciadv.abl6989. PMC 8926331. PMID 35294242.
1 2Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.
1 2 3 4 5 6 7McKenna DJ, Towers GH (1984). "Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview". J Psychoactive Drugs. 16 (4): 347–358. doi:10.1080/02791072.1984.10472305. PMID 6394730.
↑Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011(PDF). Retrieved 15 April 2025.{{cite conference}}: CS1 maint: deprecated archival service (link)
↑Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.
1 2Liechti ME, Holze F (2022). "Dosing Psychedelics and MDMA". Disruptive Psychopharmacology. Curr Top Behav Neurosci. Vol. 56. pp. 3–21. doi:10.1007/7854_2021_270. ISBN 978-3-031-12183-8. PMID 34734392.
1 2 3Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
↑Dos Santos RG, Hallak JE (November 2024). "Ayahuasca: pharmacology, safety, and therapeutic effects". CNS Spectr. 30 (1) e2. doi:10.1017/S109285292400213X. PMID 39564645. DMT has been found to be inactive orally in doses as high as 1 g, but it has been found to be psychoactive after intramuscular administration (0.25-2.00 mg/kg), when inhaled as vaporized free-base (0.2-0.7 mg/kg), and after intravenous administration (0.2-0.4 mg/kg).8–10 [...] In the case of ayahuasca, since pure DMT is not orally psychoactive (doses up to 1 g are inactive in humans51) due to peripheral (gastrointestinal and hepatic) metabolization by MAO-A, [...]
↑Barker SA (June 2022). "Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT". Psychopharmacology (Berl). 239 (6): 1749–1763. doi:10.1007/s00213-022-06065-0. PMC 8782705. PMID 35064294. Doses for vaporized or inhaled free-base DMT are typically 40–50 mg, although larger doses have been reported (100 mg; Shulgin and Shulgin 1997). Pallavicini et al. (2021) have reported that vaporization of approximately 40 mg of DMT, administered in a natural setting, produced potential electroencephalographic markers of mystical-type experiences in 35 volunteers. The onset of effects for inhaled DMT is rapid, similar to that of IV administration, but lasts less than 30 min (Riba et al. 2015; Davis et al. 2020). [...] For administration of pharmahuasca, 50 mg DMT:100 mg harmaline is usually the recommended dosage. However, combinations of 50 mg harmaline:50 mg harmine and 50 mg DMT have been tested with success. The harmalas and DMT are typically put into separate gelatin capsules, with the harmaline/harmine being taken first and the DMT being taken 15 to 20 min later. The use of moclobemide, a reversible inhibitor of MAO-A, has also been reported in DMT "pharmahuasca" studies (Kaasik et al. 2020; Ruffell et al. 2020).
↑Egger K, Aicher HD, Cumming P, Scheidegger M (September 2024). "Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors". Cell Mol Life Sci. 81 (1) 395. doi:10.1007/s00018-024-05353-6. PMC 11387584. PMID 39254764. Recent studies tested i.v. DMT with different administration regimens. Such protocols entailed 0–19.2 mg bolus 0.5–0.8 mg/min constant infusion of DMT freebase (as hemifumarate) for up to 90 min (Basel) [7], 11.2 mg bolus 1.2 mg/min infusion of DMT freebase (as fumarate) for up to 30 min (London) [8], and constant infusion totaling 13.4 mg DMT freebase (as fumarate) over 10 min (London) [110]). [...] The various β-carbolines in B. caapi, especially harmine and harmaline, enable the attainment of sufficient plasma DMT concentrations to evoke psychedelic effects lasting 4–6 h [5, 61].
1 2Ott J (1999). "Pharmahuasca: human pharmacology of oral DMT plus harmine". J Psychoactive Drugs. 31 (2): 171–177. doi:10.1080/02791072.1999.10471741. PMID 10438001. Since the β-carbolines per se could not explain the legendary psychoptic (visionary) activity of the jungle ambrosia, this had to be due to its DMT content, which amounted to an average of 29 mg/dose in the 16 potions analyzed (range: 25-36 mg/dose). [...] TABLE 1 Human Pharmacology of Psychoptic Tryptamines [...]
↑Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.
1 2Szara, Stephen; Hearst, Eliot (1962). "The 6-Hydroxylation of Tryptamines Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. ISSN 0077-8923. This correlation between metabolic transformation rates and psychological effect is suggestive. It strengthens our notion that metabolically formed 6-HDET most likely plays a role in producing the psychological effects. A more stringent test would be to give the metabolite directly to the same subjects, as was done in the animal experiments. Unfortunately we did not have enough synthetic 6-HDET to do extensive human studies, so the senior author tried it out himself. Both 1 and 2 mg. of 6-HDET had no noticeable effect. At 5 mg. there was only a very faint short-lasting perceptual disturbance. Then, on the fourth attempt, 10 mg. of 6-HDET was administered. No obvious effect on behavior occurred in the first hour, but then typical psychotomimetic disturbances began to appear. For the next 2 or 3 hours hallucinogenic effects were observed that were very similar to the effect of 60 mg. of DET. These experiments lead us to believe that 6-HDET in man is 5 to 6 times more active psychotropically than DET, but more extended studies will be necessary to establish the exact form of the relationship.
↑Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. Szara and co-workers (221,223,225) noted psychotomimetic activity for N,N-diethyltryptamine (DET; 38) at a dose of 1 mg/kg. [...] N,N-Dipropyltryptamine (DPT; 39) is also hallucinogenic in man at 1 mg/kg (222). [...] Branching of the propyl groups results in N,N-diisopropyltryptamine (DIPT; 40), which is orally active at 20 to 50 mg (202). N,N-Dibutyltryptamine (DBT; 41) and N,N-dihexyltryptamine (DHT; 42) have been examined only briefly. At 1 mg/kg, DBT produced only slight perceptual, emotional, and thinking disturbances in man, while DHT at the same dose was completely inactive (222).
↑Szára, S. (1961). "104 Correlation between Metabolism and Behavioural Action of Psychotropic Tryptamine Derivatives". Biochemical Pharmacology. 8 (1): 32. doi:10.1016/0006-2952(61)90278-7. N,N-dimethyltryptamine and its N,N-diethyl and N,N-dipropyl homologues produce autonomic symptoms, perceptual, emotional, and thinking disturbances in man (in doses of 1 mg/kg) similar to LSD25 or mescalin but for a much shorter period of time. The corresponding dibutyl derivative causes only very slight symptoms while the dihexyl compound is completely inactive in the same dose.
↑Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798. 4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].
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↑Ott J (2001). "Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics". Shamanic Snuffs or Entheogenic Errhines. Entheobotanica. pp. 99–116 (105–112, 114–115). ISBN 978-1-888755-02-2. OCLC 56061312. Retrieved 24 January 2025.
↑Hamilton Morris (1 December 2022). "A New One-Hour Talk On 5-MeO-DMT". The Hamilton Morris Podcast. Patreon. Event occurs at 6:27–8:40, 10:15–11:13. Retrieved 21 January 2025. [Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit.
↑Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 49:20–50:36. Retrieved 20 January 2025. [Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase.
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↑Hamilton Morris (29 April 2025). "POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:33:53–1:35:50. [...] [Hartsel:] The α,N,N-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug of N-methyl-AMT, which is active, or AMT itself maybe. [...]
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1 2 3 4 5 6WO 2022061242,Matthew Baggott,"Advantageous tryptamine compositions for mental disorders or enhancement",published 2023 March 24, assigned to Tactogen
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↑Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorg Med Chem Lett. 12 (2): 155–158. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343. Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.
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↑ Jayakodiarachchi N; et al. (2024). "5-MeO-DMT および関連トリプタミン類のインダゾール類似体のセロトニン受容体2アゴニストとしての評価" . ACS Med. Chem. Lett . 15 (2): 302– 309. doi : 10.1021/acsmedchemlett.3c00566 . PMC 10860182 . PMID 38352850 .
↑ "T-70 - PiHKAL·info" . Isomer Design . 2025年6月12日. 2026年3月1日取得.
↑ "T-72 - PiHKAL·info" . Isomer Design . 2025年6月12日. 2026年3月1日取得.

外部リンク

幻覚性トリプタミン類 - Wikipedia閲覧数分析（個々の幻覚性トリプタミン類に関するWikipediaページ閲覧数）

[1] Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.

[TiHKAL-2] 1 2 3 4 5 6 7 8 9Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.

[JacobShulgin1994-3] 1 2 3 4 5 6 7Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs"(PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original(PDF) on August 5, 2023.

[Shulgin2003-4] 1 2 3 4 5 6 7Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.

[Shulgin1982-5] Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.

[Shulgin1980-6] Alexander T. Shulgin (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.

[LuethiLiechti2018-7] 1 2 3 4 5Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881.

[HalberstadtChathaKlein2020-8] 1 2 3 4 5Halberstadt, Adam L.; Chatha, Muhammad; Klein, Adam K.; Wallach, Jason; Brandt, Simon D. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species"(PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Archived from the original(PDF) on 26 March 2025. Table 4 Human potency data for selected hallucinogens. [...]

[BallentineFriedmanBzdok2022-9] 1 2 3 4 5Ballentine, Galen; Friedman, Samuel Freesun; Bzdok, Danilo (March 2022). "Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences". Sci Adv. 8 (11) eabl6989. Bibcode:2022SciA....8L6989B. doi:10.1126/sciadv.abl6989. PMC 8926331. PMID 35294242.

[MallaroniMasonVinckenbosch2022-10] 1 2Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.

[McKennaTowers1984-11] 1 2 3 4 5 6 7McKenna DJ, Towers GH (1984). "Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview". J Psychoactive Drugs. 16 (4): 347–358. doi:10.1080/02791072.1984.10472305. PMID 6394730.

[Nen2011-12] Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011(PDF). Retrieved 15 April 2025.{{cite conference}}: CS1 maint: deprecated archival service (link)

[Nen2013-13] Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.

[LiechtiHolze2022-14] 1 2Liechti ME, Holze F (2022). "Dosing Psychedelics and MDMA". Disruptive Psychopharmacology. Curr Top Behav Neurosci. Vol. 56. pp. 3–21. doi:10.1007/7854_2021_270. ISBN 978-3-031-12183-8. PMID 34734392.

[HolzeSinghLiechti2024-15] 1 2 3Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.

[DosSantosHallak2024-16] Dos Santos RG, Hallak JE (November 2024). "Ayahuasca: pharmacology, safety, and therapeutic effects". CNS Spectr. 30 (1) e2. doi:10.1017/S109285292400213X. PMID 39564645. DMT has been found to be inactive orally in doses as high as 1 g, but it has been found to be psychoactive after intramuscular administration (0.25-2.00 mg/kg), when inhaled as vaporized free-base (0.2-0.7 mg/kg), and after intravenous administration (0.2-0.4 mg/kg).8–10 [...] In the case of ayahuasca, since pure DMT is not orally psychoactive (doses up to 1 g are inactive in humans51) due to peripheral (gastrointestinal and hepatic) metabolization by MAO-A, [...]

[Barker2022-17] Barker SA (June 2022). "Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT". Psychopharmacology (Berl). 239 (6): 1749–1763. doi:10.1007/s00213-022-06065-0. PMC 8782705. PMID 35064294. Doses for vaporized or inhaled free-base DMT are typically 40–50 mg, although larger doses have been reported (100 mg; Shulgin and Shulgin 1997). Pallavicini et al. (2021) have reported that vaporization of approximately 40 mg of DMT, administered in a natural setting, produced potential electroencephalographic markers of mystical-type experiences in 35 volunteers. The onset of effects for inhaled DMT is rapid, similar to that of IV administration, but lasts less than 30 min (Riba et al. 2015; Davis et al. 2020). [...] For administration of pharmahuasca, 50 mg DMT:100 mg harmaline is usually the recommended dosage. However, combinations of 50 mg harmaline:50 mg harmine and 50 mg DMT have been tested with success. The harmalas and DMT are typically put into separate gelatin capsules, with the harmaline/harmine being taken first and the DMT being taken 15 to 20 min later. The use of moclobemide, a reversible inhibitor of MAO-A, has also been reported in DMT "pharmahuasca" studies (Kaasik et al. 2020; Ruffell et al. 2020).

[EggerAicherCumming2024-18] Egger K, Aicher HD, Cumming P, Scheidegger M (September 2024). "Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors". Cell Mol Life Sci. 81 (1) 395. doi:10.1007/s00018-024-05353-6. PMC 11387584. PMID 39254764. Recent studies tested i.v. DMT with different administration regimens. Such protocols entailed 0–19.2 mg bolus 0.5–0.8 mg/min constant infusion of DMT freebase (as hemifumarate) for up to 90 min (Basel) [7], 11.2 mg bolus 1.2 mg/min infusion of DMT freebase (as fumarate) for up to 30 min (London) [8], and constant infusion totaling 13.4 mg DMT freebase (as fumarate) over 10 min (London) [110]). [...] The various β-carbolines in B. caapi, especially harmine and harmaline, enable the attainment of sufficient plasma DMT concentrations to evoke psychedelic effects lasting 4–6 h [5, 61].

[Ott1999-19] 1 2Ott J (1999). "Pharmahuasca: human pharmacology of oral DMT plus harmine". J Psychoactive Drugs. 31 (2): 171–177. doi:10.1080/02791072.1999.10471741. PMID 10438001. Since the β-carbolines per se could not explain the legendary psychoptic (visionary) activity of the jungle ambrosia, this had to be due to its DMT content, which amounted to an average of 29 mg/dose in the 16 potions analyzed (range: 25-36 mg/dose). [...] TABLE 1 Human Pharmacology of Psychoptic Tryptamines [...]

[BrimblecombePinder1975-20] Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.

[SzaraHearst1962-21] 1 2Szara, Stephen; Hearst, Eliot (1962). "The 6-Hydroxylation of Tryptamines Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. ISSN 0077-8923. This correlation between metabolic transformation rates and psychological effect is suggestive. It strengthens our notion that metabolically formed 6-HDET most likely plays a role in producing the psychological effects. A more stringent test would be to give the metabolite directly to the same subjects, as was done in the animal experiments. Unfortunately we did not have enough synthetic 6-HDET to do extensive human studies, so the senior author tried it out himself. Both 1 and 2 mg. of 6-HDET had no noticeable effect. At 5 mg. there was only a very faint short-lasting perceptual disturbance. Then, on the fourth attempt, 10 mg. of 6-HDET was administered. No obvious effect on behavior occurred in the first hour, but then typical psychotomimetic disturbances began to appear. For the next 2 or 3 hours hallucinogenic effects were observed that were very similar to the effect of 60 mg. of DET. These experiments lead us to believe that 6-HDET in man is 5 to 6 times more active psychotropically than DET, but more extended studies will be necessary to establish the exact form of the relationship.

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[Morris2022-29] Hamilton Morris (1 December 2022). "A New One-Hour Talk On 5-MeO-DMT". The Hamilton Morris Podcast. Patreon. Event occurs at 6:27–8:40, 10:15–11:13. Retrieved 21 January 2025. [Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit.

[MorrisOtt2023-30] Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 49:20–50:36. Retrieved 20 January 2025. [Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase.

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