{"id":"https://openalex.org/W2018420238","doi":"https://doi.org/10.1021/np030059u","title":"Concise Large-Scale Synthesis of Psilocin and Psilocybin, Principal Hallucinogenic Constituents of \u201cMagic Mushroom\u201d","display_name":"Concise Large-Scale Synthesis of Psilocin and Psilocybin, Principal Hallucinogenic Constituents of \u201cMagic Mushroom\u201d","publication_year":2003,"publication_date":"2003-05-30","ids":{"openalex":"https://openalex.org/W2018420238","doi":"https://doi.org/10.1021/np030059u","mag":"2018420238","pmid":"https://pubmed.ncbi.nlm.nih.gov/12828485"},"language":"en","primary_location":{"id":"doi:10.1021/np030059u","doi":"https://doi.org/10.1021/np030059u","is_oa":false,"landing_page_url":"https://doi.org/10.1021/np030059u","pdf_url":null,"source":{"id":"https://openalex.org/S166799026","display_name":"Journal of Natural Products","issn_l":"0163-3864","issn":["0163-3864","1520-6025"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","doyens","jufo-1","ki-jl-1","medline","norway-2","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Natural Products","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5045294044","display_name":"Osamu Shirota","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210151964","display_name":"National Institute of Health Sciences","ror":"https://ror.org/04s629c33","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1333985979","https://openalex.org/I4210151964"]}],"countries":["JP"],"is_corresponding":true,"raw_author_name":"Osamu Shirota","raw_affiliation_strings":["Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan","institution_ids":["https://openalex.org/I4210151964"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5058882649","display_name":"Wataru Hakamata","orcid":"https://orcid.org/0000-0002-1254-9717","observed_orcids":["https://orcid.org/0000-0002-1254-9717"]},"institutions":[{"id":"https://openalex.org/I4210151964","display_name":"National Institute of Health Sciences","ror":"https://ror.org/04s629c33","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1333985979","https://openalex.org/I4210151964"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Wataru Hakamata","raw_affiliation_strings":["Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan","institution_ids":["https://openalex.org/I4210151964"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5053797637","display_name":"Yukihiro Goda","orcid":"https://orcid.org/0000-0001-5617-3670","observed_orcids":["https://orcid.org/0000-0001-5617-3670"]},"institutions":[{"id":"https://openalex.org/I4210151964","display_name":"National Institute of Health Sciences","ror":"https://ror.org/04s629c33","country_code":"JP","type":"facility","lineage":["https://openalex.org/I1333985979","https://openalex.org/I4210151964"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yukihiro Goda","raw_affiliation_strings":["Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Pharmacognosy, Phytochemistry and Narcotics, and Division of Organic Chemistry, National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan","institution_ids":["https://openalex.org/I4210151964"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5045294044"],"corresponding_institution_ids":["https://openalex.org/I4210151964"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":3.6705,"has_fulltext":false,"cited_by_count":87,"citation_normalized_percentile":{"value":0.91877305,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"66","issue":"6","first_page":"885","last_page":"887"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T12553","display_name":"Psychedelics and Drug Studies","score":0.9609000086784363,"subfield":{"id":"https://openalex.org/subfields/3203","display_name":"Clinical Psychology"},"field":{"id":"https://openalex.org/fields/32","display_name":"Psychology"},"domain":{"id":"https://openalex.org/domains/2","display_name":"Social Sciences"}},"topics":[{"id":"https://openalex.org/T12553","display_name":"Psychedelics and Drug Studies","score":0.9609000086784363,"subfield":{"id":"https://openalex.org/subfields/3203","display_name":"Clinical Psychology"},"field":{"id":"https://openalex.org/fields/32","display_name":"Psychology"},"domain":{"id":"https://openalex.org/domains/2","display_name":"Social Sciences"}},{"id":"https://openalex.org/T13188","display_name":"Synthesis and bioactivity of alkaloids","score":0.009700000286102295,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T13649","display_name":"Advanced Synthetic Organic Chemistry","score":0.008100000210106373,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/psilocin","display_name":"psilocin","score":0.9919999837875366},{"id":"https://openalex.org/keywords/psilocybin","display_name":"psilocybin","score":1.0},{"id":"https://openalex.org/keywords/magic-mushrooms","display_name":"magic mushrooms","score":0.7630000114440918},{"id":"https://openalex.org/keywords/hallucinogens","display_name":"hallucinogens","score":0.7269999980926514},{"id":"https://openalex.org/keywords/large-scale-synthesis","display_name":"large-scale synthesis","score":0.9049999713897705},{"id":"https://openalex.org/keywords/zwitterionic-intermediate","display_name":"zwitterionic intermediate","score":0.8920000195503235},{"id":"https://openalex.org/keywords/chromatography-free-synthesis","display_name":"chromatography-free synthesis","score":0.6919999718666077}],"concepts":[{"id":"https://openalex.org/C2776502132","wikidata":"https://www.wikidata.org/wiki/Q208118","display_name":"Psilocybin","level":3,"score":0.9895551204681396},{"id":"https://openalex.org/C124315065","wikidata":"https://www.wikidata.org/wiki/Q194270","display_name":"Hallucinogen","level":2,"score":0.7961397171020508},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5962737798690796},{"id":"https://openalex.org/C2776474821","wikidata":"https://www.wikidata.org/wiki/Q83093","display_name":"Mushroom","level":2,"score":0.521787166595459},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.45533695816993713},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.1761796772480011},{"id":"https://openalex.org/C31903555","wikidata":"https://www.wikidata.org/wiki/Q1637030","display_name":"Food science","level":1,"score":0.08394730091094971},{"id":"https://openalex.org/C98274493","wikidata":"https://www.wikidata.org/wiki/Q128406","display_name":"Pharmacology","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000363","descriptor_name":"Agaricales","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D006213","descriptor_name":"Hallucinogens","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D006213","descriptor_name":"Hallucinogens","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D006213","descriptor_name":"Hallucinogens","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011562","descriptor_name":"Psilocybin","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":true},{"descriptor_ui":"D011562","descriptor_name":"Psilocybin","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D011562","descriptor_name":"Psilocybin","qualifier_ui":"Q000494","qualifier_name":"pharmacology","is_major_topic":false},{"descriptor_ui":"D011562","descriptor_name":"Psilocybin","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D019906","descriptor_name":"Nuclear Magnetic Resonance, Biomolecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020650","descriptor_name":"Combinatorial Chemistry Techniques","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true}],"locations_count":3,"locations":[{"id":"doi:10.1021/np030059u","doi":"https://doi.org/10.1021/np030059u","is_oa":false,"landing_page_url":"https://doi.org/10.1021/np030059u","pdf_url":null,"source":{"id":"https://openalex.org/S166799026","display_name":"Journal of Natural Products","issn_l":"0163-3864","issn":["0163-3864","1520-6025"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-b","doyens","jufo-1","ki-jl-1","medline","norway-2","poland-100","russia-white-list-1"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Natural Products","raw_type":"journal-article"},{"id":"pmid:12828485","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/12828485","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of natural products","raw_type":"Journal Article"},{"id":"pmh:oai:CiteSeerX.psu:10.1.1.925.6269","doi":null,"is_oa":false,"landing_page_url":"http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.925.6269","pdf_url":null,"source":null,"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"https://erowid.org/archive/rhodium/pdf/psilocin-psilocybin.large-scale.pdf","raw_type":"text"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":19,"referenced_works":["https://openalex.org/W1981430494","https://openalex.org/W1981598408","https://openalex.org/W1983791578","https://openalex.org/W1997058647","https://openalex.org/W2012142575","https://openalex.org/W2014259651","https://openalex.org/W2039619190","https://openalex.org/W2046152571","https://openalex.org/W2048765492","https://openalex.org/W2057174717","https://openalex.org/W2064468738","https://openalex.org/W2067781771","https://openalex.org/W2071084276","https://openalex.org/W2076730931","https://openalex.org/W2083724292","https://openalex.org/W2089982466","https://openalex.org/W2094947385","https://openalex.org/W2148875730","https://openalex.org/W2165984877"],"related_works":["https://openalex.org/W2394684358","https://openalex.org/W2417841453","https://openalex.org/W7145610319","https://openalex.org/W2999478951","https://openalex.org/W2950394635","https://openalex.org/W2023331513","https://openalex.org/W1974109667","https://openalex.org/W2403125288","https://openalex.org/W7171924130","https://openalex.org/W108080335"],"abstract_inverted_index":{"The":[0,22],"concise":[1],"large-scale":[2],"syntheses":[3],"of":[4,14,28,33,49],"psilocin":[5],"(1)":[6],"and":[7],"psilocybin":[8],"(2),":[9],"the":[10,26,31,34],"principal":[11],"hallucinogenic":[12],"constituents":[13],"\"magic":[15],"mushroom\",":[16],"were":[17],"achieved":[18],"without":[19],"chromatographic":[20],"purification.":[21],"key":[23],"step":[24],"in":[25],"synthesis":[27],"2":[29],"was":[30,44],"isolation":[32],"dibenzyl-protected":[35],"intermediate":[36],"(7)":[37],"as":[38],"a":[39],"zwitterionic":[40],"derivative":[41],"(8),":[42],"which":[43],"completely":[45],"identified":[46],"by":[47],"means":[48],"2D":[50],"NMR":[51],"analyses.":[52]},"counts_by_year":[{"year":2026,"cited_by_count":5},{"year":2025,"cited_by_count":11},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":7},{"year":2022,"cited_by_count":12},{"year":2021,"cited_by_count":6},{"year":2020,"cited_by_count":10},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":5},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}