David Repke
David Repke, or David B. Repke, is an American medicinal chemist who has done work in the area of psychedelic drugs. He and his colleagues are known to have been the first to synthesize and describe a number of notable psychedelic tryptamines, including 4-HO-MET, 4-HO-MPT, 4-HO-DPT, 4-HO-DBT, 4-HO-DiPT, MiPT, 4-HO-MiPT, 5-MeO-MiPT, 4-HO-McPeT, and 4-HO-pyr-T, among others. He is known to have collaborated with Alexander Shulgin and Dennis McKenna on scientific work. Repke has also published a book on the entheogenic use of Anadenanthera in South America that was coauthored with Constantino Manuel Torres.
David B. Repke BSc | |
|---|---|
| Other names | David B. Repke |
| Alma mater | Michigan Technological University (BSc; 1966–1970) |
| Occupation | Medicinal chemist |
| Years active | 1973–2010[1][2] |
| Employer(s) | Syntex, Roche |
| Known for | Work in the area of psychedelic tryptamines |
| Notable work | Anadenanthera: Visionary Plant of Ancient South America (2006)[3] |
| Website | www.linkedin.com/in/david-repke-bb5b6343/ |
David Repke, or David B. Repke, is an American medicinal chemist who has done work in the area of psychedelic drugs.[4][5][6][3] He and his colleagues are known to have been the first to synthesize and describe a number of notable psychedelic tryptamines,[6][5] including 4-HO-MET,[5][7] 4-HO-MPT,[7] 4-HO-DPT,[8][5][9] 4-HO-DBT,[9] 4-HO-DiPT,[10][11][9] MiPT,[12][7][13] 4-HO-MiPT,[5][7] 5-MeO-MiPT,[4][14][13] 4-HO-McPeT,[7] and 4-HO-pyr-T,[9] among others. He is known to have collaborated with Alexander Shulgin and Dennis McKenna on scientific work.[14][3][13][15] Repke has also published a book on the entheogenic use of Anadenanthera in South America that was coauthored with Constantino Manuel Torres.[3]
Selected publications
[edit]Books
[edit]- Torres, Constantino Manuel; Repke, David B. (2006). Anadenanthera: Visionary Plant of Ancient South America. Routledge. doi:10.4324/9781315864594. ISBN 978-1-315-86459-4.
Journal articles
[edit]- Repke, David B.; Ferguson, Wilfred J. (1976). "Synthesis of S (+) and R (-)-3-(2-aminopropyl)indole from ethyl- D - and L -tryptophanate". Journal of Heterocyclic Chemistry. 13 (4): 775–778. doi:10.1002/jhet.5570130417. ISSN 0022-152X. Retrieved 8 October 2025.
- Repke, David B.; Leslie, Dale Thomas (1977). "Baeocystin in Psilocybe semilanceata". Journal of Pharmaceutical Sciences. 66 (1): 113–114. Bibcode:1977JPhmS..66..113R. doi:10.1002/jps.2600660130. PMID 556766. Retrieved 8 October 2025.
- Ferguson WJ, Bates DK, Repke DB (1977). "Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols". Journal of Heterocyclic Chemistry. 14 (1): 71–74. doi:10.1002/jhet.5570140113. ISSN 0022-152X.
- Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN 0022-152X.
- Repke, David B.; Ferguson, Wilfred J. (1982). "Psilocin analogs. III. Synthesis of 5-methoxy- and 5-hydroxy-1,2,3,4-tetrahydro-9 H -pyrido[3,4- b ]indoles". Journal of Heterocyclic Chemistry. 19 (4): 845–848. doi:10.1002/jhet.5570190428. ISSN 0022-152X. Retrieved 8 October 2025.
- Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". J Med Chem. 28 (7): 892–896. doi:10.1021/jm00145a007. PMID 4009612.
- McKenna DJ, Repke DB, Peroutka SJ (1989). "Hallucinogenic indolealkylamines are selective for 5HT2A binding sites". Neuroscience Abstract. 15: 485–.
- McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186.
- Torres, Constantino Manuel; Repke, David B.; Chan, Kelvin; McKenna, Dennis; Llagostera, Agustin; Schultes, Richard Evans (1991). "Snuff Powders from Pre-Hispanic San Pedro de Atacama: Chemical and Contextual Analysis". Current Anthropology. 32 (5): 640–649. doi:10.1086/204014. ISSN 0011-3204. Retrieved 8 October 2025.
- Repke, David B.; Artis, Dean R.; Nelson, Janis T.; Wong, Erik H. F. (1994). "Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques". The Journal of Organic Chemistry. 59 (8): 2164–2171. doi:10.1021/jo00087a037. ISSN 0022-3263. Retrieved 8 October 2025.
Book chapters
[edit]- Torres CM, Repke D (1996). "The use of Anadenanthera colubrina var. cebil by Wichi (Mataco) Shamans of the Chaco Central, Argentina". Yearbook for Ethnomedicine and the Study of Consciousness. Vol. 5. pp. 41–58.
See also
[edit]References
[edit]- ^ Repke DB, Mandell DM, Thomas JH (June 1973). "Alkaloids of Acacia baileyana". Lloydia. 36 (2): 211–213. PMID 4744559.
- ^ Harris RN, Stabler RS, Repke DB, Kress JM, Walker KA, Martin RS, Brothers JM, Ilnicka M, Lee SW, Mirzadegan T (June 2010). "Highly potent, non-basic 5-HT6 ligands. Site mutagenesis evidence for a second binding mode at 5-HT6 for antagonism". Bioorg Med Chem Lett. 20 (11): 3436–3440. doi:10.1016/j.bmcl.2010.03.110. PMID 20434910.
- ^ a b c d Torres, Constantino Manuel; Repke, David B. (2006). Anadenanthera: Visionary Plant of Ancient South America. Routledge. doi:10.4324/9781315864594. ISBN 978-1-315-86459-4.
[Alexander Shulgin in Preface:] It was several years earlier that I had first met David Repke. At that time he was an organic chemist with a northern California pharmaceutical company, and I quickly appreciated that he was a master in the area of tryptamine chemistry. He was interested in the synthesis of plant alkaloids and their analogues, and this fit beautifully with my own curiosity about psychoactive compounds. Our interaction has led to our co-authoring of a couple of publications in the scientific literature. At that time, our mutual interests were focused on the N-alkylated analogues of the active ayahuasca component dimethyltryptamine and the four-substituted counterparts such as psilocin and psilocybin that are the major contributors to the activity of the magic mushrooms of the Psilocybe genus.
- ^ a b Aragón, Matthew (9 January 2024). "Meet Moxy: The Novel Psychedelic the DEA Tried To Ban". DoubleBlind Mag. Retrieved 8 October 2025.
5-MeO-MiPT is a fully synthetic compound first created in 1985, the brainchild of pioneering medicinal chemists Alexander "Sasha" Shulgin and David B. Repke. Its synthesis was part of an effort to investigate how small changes to a drug's chemical structure could influence the effects it produces when consumed—a concept in drug discovery research known as the "structure-activity relationship." Shulgin and Repke published their report of 5-MeO-MiPT's synthesis and pharmacological effects in the Journal of Medicinal Chemistry, marking the first documented evidence of the drug's existence.
- ^ a b c d e Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. PMID 33860183.
Repke synthesized several other psilocin homologues, including 4-hydroxy-N-methyl-N-ethyltryptamine (4-HO-MET), 4-hydroxy-N-methyl-N-isopropyltryptamine (4-HO-MIPT), 4-hydroxy-N,N-dipropyltryptamine (4-HO-DPT), and 4-hydroxy-N,N-diisopropyltryptamine (4-HO-DIPT).63,64
- ^ a b Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E (2018). "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. 12 54. doi:10.3389/fnint.2018.00054. PMC 6235949. PMID 30467466.
5-MeO-MiPT (5-Methoxy-N-methyl-N-isopropyltryptamine): substituted tryptamine, first synthesized by Repke et al. (1985). [...] 4-OH-DiPT (4-Hydroxy-diisopropyltryptamine): substituted tryptamine, first synthesized by Repke et al. (1977) and investigated in humans by A. Shulgin (Shulgin and Shulgin, 1997).
- ^ a b c d e Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN 0022-152X.
- ^ Bauer, Barbara E. (2 January 2020). "Scientists Solve the Crystal Structure of the Psilocbyin Derviative 4-HO-DPT". Psychedelic Science Review. Retrieved 8 October 2025.
- ^ a b c d Ferguson WJ, Bates DK, Repke DB (1977). "Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols". Journal of Heterocyclic Chemistry. 14 (1): 71–74. doi:10.1002/jhet.5570140113. ISSN 0022-152X.
- ^ "4-HO-DiPT". Psychedelic Science Review. 23 June 2022. Retrieved 8 October 2025.
In 1977, David Repke first synthesized 4-HO-DiPT hydrochloride.1 Shulgin and Shulgin subsequently reported synthesizing 4-HO-DiPT hydrochloride in TIHKAL.2 Neither Repke nor the Shulgins isolated or characterized the freebase form of 4-HO-DiPT or any salts other than the hydrochloride.
- ^ "CaaMTech Creates Two New Prodrugs of 4-HO-DiPT". Psychedelic Invest. 22 September 2022. Retrieved 8 October 2025.
4-HO-DiPT was first synthesized and characterized as the hydrochloride salt by David Repke in 1977. Its profound psychedelic effects were described by Alexander and Ann Shulgin in their book TiHKAL: "I truly doubt that there is another psychedelic drug, anywhere, that can match this one for speed, for intensity, for brevity, and sensitive to dose, at least one that is active orally."
- ^ Chadeayne AR, Pham DN, Golen JA, Manke DR (September 2019). "The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin". Acta Crystallographica Section E. 75 (Pt 9): 1316–1320. Bibcode:2019AcCrE..75.1316C. doi:10.1107/S2056989019011253. PMC 6727059. PMID 31523457.
The synthesis of N-methyl-N-isopropyltryptamine (MiPT) was reported in 1981 (Repke et al., 1981). In 1985, Repke and co-workers reported that of the compounds in the series of N,N-dialkyl-4-hydroxytryptamines, the N-methyl-N-isopropyl derivative (4-HO-MiPT) is the most potent based upon qualitative effects on humans (Repke et al., 1985).
- ^ a b c Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". J Med Chem. 28 (7): 892–896. doi:10.1021/jm00145a007. PMID 4009612.
- ^ a b Briggs, Saga (9 April 2025). "The next era of psychedelics may be precision-designed states of consciousness". Freethink. Retrieved 8 October 2025.
Though you may never have heard of it, moxy is far from new. It was synthesized in 1985 in a lab in Lafayette, California, by medical chemists Alexander "Sasha" Shulgin and David B. Repke. Shulgin synthesized most of the world's psychedelic drugs and tested many of them on himself and his wife Ann, documenting their effects in books like "TiHKAL" ("Tryptamines I Have Known and Loved") and "PiHKAL" ("Phenethylamines I Have Known and Loved").
- ^ McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186.