David Repke

{{Short description|Chemist}} {{Infobox person | name = David B. Repke | honorific_suffix = BSc | image = | alt = | caption = | birth_date = | birth_place = | death_date = | death_place = | other_names = David B. Repke | alma_mater = Michigan Technological University (BSc; 1966–1970) | occupation = Medicinal chemist | years_active = 1973–2010<ref name="RepkeMandellThomas1973">{{cite journal | vauthors = Repke DB, Mandell DM, Thomas JH | title = Alkaloids of Acacia baileyana | journal = Lloydia | volume = 36 | issue = 2 | pages = 211–213 | date = June 1973 | pmid = 4744559 | doi = | url = }}</ref><ref name="HarrisStablerRepke2010">{{cite journal | vauthors = Harris RN, Stabler RS, Repke DB, Kress JM, Walker KA, Martin RS, Brothers JM, Ilnicka M, Lee SW, Mirzadegan T | title = Highly potent, non-basic 5-HT6 ligands. Site mutagenesis evidence for a second binding mode at 5-HT6 for antagonism | journal = Bioorg Med Chem Lett | volume = 20 | issue = 11 | pages = 3436–3440 | date = June 2010 | pmid = 20434910 | doi = 10.1016/j.bmcl.2010.03.110 | url = }}</ref> | employer = Syntex, Roche | known_for = Work in the area of psychedelic tryptamines | notable_works = ''Anadenanthera: Visionary Plant of Ancient South America'' (2006)<ref name="TorresRepke2006" /> | website = {{URL|https://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.<ref name="Aragon2024" /><ref name="KleinChathaLaskowski2021" /><ref name="ZamberlanSanzMartínez2018">{{cite journal | vauthors = Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E | title = 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 | journal = Front Integr Neurosci | volume = 12 | issue = | article-number = 54 | date = 2018 | pmid = 30467466 | pmc = 6235949 | doi = 10.3389/fnint.2018.00054 | doi-access = free | url = | quote = 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).}}</ref><ref name="TorresRepke2006">{{cite book | last1=Torres | first1=Constantino Manuel | last2=Repke | first2=David B. | title=Anadenanthera: Visionary Plant of Ancient South America | publisher=Routledge | date=2006 | isbn=978-1-315-86459-4 | doi=10.4324/9781315864594 | url=https://books.google.com/books?id=cMSFT5K3C9wC&pg=PP1 | quote = [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.}}</ref><ref name="MorrisMcKenna2022">{{cite podcast | url=https://www.patreon.com/posts/pod-44-new-with-64560770 | title=Pod 44: New natural psychedelics with Dr. Dennis McKenna | website=The Hamilton Morris Podcast | publisher=Patreon | host=Hamilton Morris | date=31 March 2022 | time=1:34:00–1:36:28}}</ref> He and his colleagues are known to have been the first to synthesize and describe a number of notable psychedelic tryptamines,<ref name="ZamberlanSanzMartínez2018" /><ref name="KleinChathaLaskowski2021" /> including 4-HO-MET,<ref name="KleinChathaLaskowski2021">{{cite journal | vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL | title = Investigation of the Structure-Activity Relationships of Psilocybin Analogues | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 533–542 | date = April 2021 | pmid = 33860183 | pmc = 8033608 | doi = 10.1021/acsptsci.0c00176 | url = | quote = 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}}</ref><ref name="RepkeFergusonBates1981">{{cite journal | vauthors = Repke DB, Ferguson WJ, Bates DK | title=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=Journal of Heterocyclic Chemistry | volume=18 | issue=1 | date=1981 | issn=0022-152X | doi=10.1002/jhet.5570180131 | pages=175–179}}</ref> 4-HO-MPT,<ref name="RepkeFergusonBates1981" /> 4-HO-DPT,<ref name="PSR2020">{{cite web | last=Bauer | first=Barbara E. | title=Scientists Solve the Crystal Structure of the Psilocbyin Derviative 4-HO-DPT | website=Psychedelic Science Review | date=2 January 2020 | url=https://psychedelicreview.com/scientists-solve-the-crystal-structure-of-the-psilocbyin-derviative-4-ho-dpt/ | access-date=8 October 2025}}</ref><ref name="KleinChathaLaskowski2021" /><ref name="FergusonBatesRepke1977" /> 4-HO-DBT,<ref name="FergusonBatesRepke1977" /> 4-HO-DiPT,<ref name="PSR2022">{{cite web | title=4-HO-DiPT | website=Psychedelic Science Review | date=23 June 2022 | url=https://psychedelicreview.com/compound/4-ho-dipt/ | access-date=8 October 2025 | quote=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.}}</ref><ref name="PsychedelicInvest2022">{{cite web | title=CaaMTech Creates Two New Prodrugs of 4-HO-DiPT | website=Psychedelic Invest | date=22 September 2022 | url=https://psychedelicinvest.com/caamtech-creates-two-new-prodrugs-of-4-ho-dipt/ | access-date=8 October 2025 | quote=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.”}}</ref><ref name="FergusonBatesRepke1977" /> MiPT,<ref name="ChadeaynePhamGolen2019">{{cite journal | vauthors = Chadeayne AR, Pham DN, Golen JA, Manke DR | title = The fumarate salts of the N-isopropyl-N-methyl derivatives of DMT and psilocin | journal = Acta Crystallographica Section E| volume = 75 | issue = Pt 9 | pages = 1316–1320 | date = September 2019 | pmid = 31523457 | pmc = 6727059 | doi = 10.1107/S2056989019011253 | doi-access = free| bibcode = 2019AcCrE..75.1316C | url = | quote = 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).}}</ref><ref name="RepkeFergusonBates1981" /><ref name="RepkeGrotjahnShulgin1985" /> 4-HO-MiPT,<ref name="KleinChathaLaskowski2021" /><ref name="RepkeFergusonBates1981" /> 5-MeO-MiPT,<ref name="Aragon2024">{{cite web | last=Aragón | first=Matthew | title=Meet Moxy: The Novel Psychedelic the DEA Tried To Ban | website=DoubleBlind Mag | date=9 January 2024 | url=https://doubleblindmag.com/what-is-moxy/ | access-date=8 October 2025 | quote=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.}}</ref><ref name="Briggs2025">{{cite web | last=Briggs | first=Saga | title=The next era of psychedelics may be precision-designed states of consciousness | website=Freethink | date=9 April 2025 | url=https://www.freethink.com/biotech/ai-psychedelics-mindstate | access-date=8 October 2025 | quote=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”).}}</ref><ref name="RepkeGrotjahnShulgin1985">{{cite journal | vauthors = Repke DB, Grotjahn DB, Shulgin AT | title = Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents | journal = J Med Chem | volume = 28 | issue = 7 | pages = 892–896 | date = July 1985 | pmid = 4009612 | doi = 10.1021/jm00145a007 | url = }}</ref> 4-HO-McPeT,<ref name="RepkeFergusonBates1981" /> and 4-HO-pyr-T,<ref name="FergusonBatesRepke1977">{{cite journal | vauthors = Ferguson WJ, Bates DK, Repke DB | title = Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols | journal = Journal of Heterocyclic Chemistry | volume = 14 | issue = 1 | pages = 71–74 | date = 1977 | doi = 10.1002/jhet.5570140113 | issn = 0022-152X | doi-access = free }}</ref> among others.<ref name="MorrisMcKenna2022" /> He is known to have collaborated with Alexander Shulgin and Dennis McKenna on scientific work.<ref name="Briggs2025" /><ref name="TorresRepke2006" /><ref name="RepkeGrotjahnShulgin1985" /><ref name="McKennaRepke1990">{{cite journal | vauthors = McKenna DJ, Repke DB, Lo L, Peroutka SJ | title = Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes | journal = Neuropharmacology | volume = 29 | issue = 3 | pages = 193–198 | date = March 1990 | pmid = 2139186 | doi = 10.1016/0028-3908(90)90001-8 | url = }}</ref> Both Repke and Shulgin conducted self-experimentation with the novel psychedelics they developed.<ref name="MorrisMcKenna2022" /> Repke has also published a book on the entheogenic use of ''Anadenanthera'' in South America that was coauthored with Constantino Manuel Torres.<ref name="TorresRepke2006" />

==Selected publications== ===Books=== * {{cite book | last1=Torres | first1=Constantino Manuel | last2=Repke | first2=David B. | title=Anadenanthera: Visionary Plant of Ancient South America | publisher=Routledge | date=2006 | isbn=978-1-315-86459-4 | doi=10.4324/9781315864594 | url=https://books.google.com/books?id=cMSFT5K3C9wC&pg=PP1}}

===Journal articles=== * {{cite journal | last1=Repke | first1=David B. | last2=Ferguson | first2=Wilfred J. | title=Synthesis of S (+) and R (-)-3-(2-aminopropyl)indole from ethyl- D - and L -tryptophanate | journal=Journal of Heterocyclic Chemistry | volume=13 | issue=4 | date=1976 | issn=0022-152X | doi=10.1002/jhet.5570130417 | pages=775–778 | url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570130417 | access-date=8 October 2025| url-access=subscription }} * {{cite journal | last1=Repke | first1=David B. | last2=Leslie | first2=Dale Thomas | title=Baeocystin in Psilocybe semilanceata | journal=Journal of Pharmaceutical Sciences | volume=66 | issue=1 | date=1977 | doi=10.1002/jps.2600660130 | pages=113–114 | pmid=556766 | bibcode=1977JPhmS..66..113R | url=https://linkinghub.elsevier.com/retrieve/pii/S0022354915391450 | access-date=8 October 2025| url-access=subscription }} * {{cite journal | vauthors = Ferguson WJ, Bates DK, Repke DB | title = Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols | journal = Journal of Heterocyclic Chemistry | volume = 14 | issue = 1 | pages = 71–74 | date = 1977 | doi = 10.1002/jhet.5570140113 | issn = 0022-152X | doi-access = free }} * {{cite journal | vauthors = Repke DB, Ferguson WJ, Bates DK | title=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=Journal of Heterocyclic Chemistry | volume=18 | issue=1 | date=1981 | issn=0022-152X | doi=10.1002/jhet.5570180131 | pages=175–179}} * {{cite journal | last1=Repke | first1=David B. | last2=Ferguson | first2=Wilfred J. | title=Psilocin analogs. III. Synthesis of 5-methoxy- and 5-hydroxy-1,2,3,4-tetrahydro-9 H -pyrido[3,4- b ]indoles | journal=Journal of Heterocyclic Chemistry | volume=19 | issue=4 | date=1982 | issn=0022-152X | doi=10.1002/jhet.5570190428 | pages=845–848 | url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570190428 | access-date=8 October 2025| url-access=subscription }} * {{cite journal | vauthors = Repke DB, Grotjahn DB, Shulgin AT | title = Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents | journal = J Med Chem | volume = 28 | issue = 7 | pages = 892–896 | date = July 1985 | pmid = 4009612 | doi = 10.1021/jm00145a007 | url = }} * {{cite journal | vauthors = McKenna DJ, Repke DB, Peroutka SJ | title = Hallucinogenic indolealkylamines are selective for 5HT2A binding sites | date = 1989 | journal = Neuroscience Abstract | volume = 15 | pages = 485– | url = https://scholar.google.com/scholar?cluster=18382692055770031750}} * {{cite journal | vauthors = McKenna DJ, Repke DB, Lo L, Peroutka SJ | title = Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes | journal = Neuropharmacology | volume = 29 | issue = 3 | pages = 193–198 | date = March 1990 | pmid = 2139186 | doi = 10.1016/0028-3908(90)90001-8 | url = }} * {{cite journal | last1=Torres | first1=Constantino Manuel | last2=Repke | first2=David B. | last3=Chan | first3=Kelvin | last4=McKenna | first4=Dennis | last5=Llagostera | first5=Agustin | last6=Schultes | first6=Richard Evans | title=Snuff Powders from Pre-Hispanic San Pedro de Atacama: Chemical and Contextual Analysis | journal=Current Anthropology | volume=32 | issue=5 | date=1991 | issn=0011-3204 | doi=10.1086/204014 | pages=640–649 | url=https://www.journals.uchicago.edu/doi/10.1086/204014 | access-date=8 October 2025| url-access=subscription }} * {{cite journal | last1=Repke | first1=David B. | last2=Artis | first2=Dean R. | last3=Nelson | first3=Janis T. | last4=Wong | first4=Erik H. F. | title=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 | journal=The Journal of Organic Chemistry | volume=59 | issue=8 | date=1994 | issn=0022-3263 | doi=10.1021/jo00087a037 | pages=2164–2171 | url=https://pubs.acs.org/doi/abs/10.1021/jo00087a037 | access-date=8 October 2025| url-access=subscription }}

===Book chapters=== * {{cite book | vauthors = Torres CM, Repke D | date = 1996 | chapter = The use of Anadenanthera colubrina var. cebil by Wichi (Mataco) Shamans of the Chaco Central, Argentina | pages = 41–58 | title = Yearbook for Ethnomedicine and the Study of Consciousness | volume = 5 | url = https://www.researchgate.net/publication/313727941}}

==References== {{Reflist}}

==External links== * [https://www.linkedin.com/in/david-repke-bb5b6343/ David Repke - LinkedIn]

Category:20th-century American chemists Category:21st-century American chemists Category:American pharmacologists Category:David Repke Category:Living people Category:Michigan Technological University alumni Category:Psychedelic chemists Category:Psychedelic drug researchers Category:Psychopharmacologists Category:Scientists from California Category:Year of birth missing (living people)