DOCSLIB.ORG

Aspects Op Secondary Metabolism in Basidiqmycetes

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Aspects Op Secondary Metabolism in Basidiqmycetes ASPECTS OP SECONDARY METABOLISM IN BASIDIQMYCETES BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS A SURVEY OF PHENOL-O-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS by by.' . WEI-WEI/WANG B.Sc, National Taiwan University, 1974 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in THE FACULTY OF GRADUATE STUDIES (DEPARTMENT OF BOTANY) We accept 'this thesis as conforming to the required standard THE UNIVERSITY OF BRITISH COLUMBIA November, 1977 f7\ Wei-Wei Wang, 1977 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the Head of my Department or by his representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department of Botany The University of British Columbia 2075 Wesbrook Place Vancouver, Canada V6T 1W5 Date December 6. 1977 ii ABSTRACT I. Psilocybe cubensis was cultured successfully in two media. Medium A was devised by Catalfomo and Tyler and Medium B was a modification of a medium which has been used for ergot alkaloid production by Claviceps purpurea. Only when the fungus was kept on Sabouraud agar plates.did it subsequently produce psilocybin when transferred to liquid media. A quantitative time-course study of psilocybin production in the two media was carried out. Maximal production appeared on the fifth day. The activities of an acid phosphatase, acting on psilocybin, were measured from mycelia grown in the two media. Enzyme activity from the A culture was very high and a blue color caused by oxidation of psilocin formed in five minutes. The effect of adding L-tryptophan on alkaloid production as well as 14 the fate of tryptophan-C was also investigated. Tryptophan stimulated significantly psilocybin production in the very beginning in the B medium. The degradation of tryptophan was different in the two media. It was converted to kynurenine and anthranilic acid in A medium and to tryptamine in tryptophan added B medium (B' medium). Radioactive D,L-tryptophan side chain labeled, gave labeled psilocin and psilocybin. Potassium deficiency decreased psilocybin production while a potassium supplement had no effect. The fungus did not produce polyacetylenic compounds in the medium but ergosterol was detected as a major acetate derived metabolite when the fungus was kept on MYP agar plates and transferred subsequently to liquid media. Psilocin has very slight anti• biotic activity against Candida albicans whereas psilocybin has none. iii II. Eight species of Lentinus and Lentinellus. were investigated for the occurrence of a phenol-O-methyltransferase. Only Lentinus lepideus and Lentinus pbnderbsus showed enzyme activity in both light and dark conditions. The specificity of the enzyme for a number of substrates was also examined. Of six compounds tested, methyl p-coumarate, methyl caffeate and methyl ferulate.served-as substrates. The products of enzymic activity were identified-by radioautography. iv TABLE OF CONTENTS PAGE ABSTRACT ii TABLE OF CONTENTS;. iv LIST OF TABLES vi LIST OF FIGURES vii ACKNOWLEDGEMENT ix I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS INTRODUCTION 1 REVIEW OF LITERATURE 3 MATERIALS AND METHODS A. Chemicals 13 B. Medium and culture 15 C. Analytical methods 17 D. Radioautography 20 E. Psilocybin phosphatase activity 21 F. Potassium nutrition and psilocybin production 23 G. Test of UV-mediated antibiotic and phototoxic activities of medium, psilocin and psilocybin 24 EXPERIMENTAL AND RESULTS A. Chromatographic separation and identification of tryptophan metabolites 25 B. pH, Growth and morphological difference of cultures 26 C. Psilocybin production 27 D. Formation of psilocybin and psilocin from tryptophan 28 V E. Phosphatase activity 39 F. Psilocybin production and potassium nutrition 39 G. Ehrlich-positive compounds in the extracts 42 H. Tryptophan concentration in the medium 42 I. Antibiotic activity of psilocin, psilocybin and medium filtrate 49 J. Identification of d(-)mannitol 49 DISCUSSION 54 LITERATURE CITED 63 II. A SURVEY OF PHENOL-0-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS INTRODUCTION 69 MAT ERI AL S A ANDI1ME THOD S A. Chemicals 73 B. Medium and culture 74 C. Extraction of enzyme 75 D. Enzyme assay 75 E. Identification of reaction products 76 F. Protein concentration 76 RESULTS AND DISCUSSION 77 LITERATURE CITED 81 vi LIST OF TABLES page I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1. Some Tryptamine Derivatives Found in Fungi 3 2. Fungi Containing Psilocybin 6 3. Composition of A-medium 15 4. Composition of B-medium 16 5. Fluorescence, Color Reaction and R^ Values of Some Tryptophan Metabolites 25 6. Distribution of Radioactivity in Tryptophan, Psilocybin and Psilocin of Mycelium Extract, 14 Administered D,L-Tryptophan, side chain-3-C 28 7. The Growth, pH of Medium and Psilocybin Production of B-medium, Potassium Deficient and Supplement Media 39 II. A SURVEY OF PHENOL-0-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS 1. Substrates Specificity of Methylating Enzymes from Lentinus ponderosus and Lentinus lepideus 78 vii LIST OF FIGURES page I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1. Locations of some standard tryptophan metabolites on a two-dimensional cellulose thin layer plate 29 2. pH of A and A' media 30 3. pH of B and B' media 31 4. Growth rate of fungal cells in A and A' media 32 5. Growth rate of fungal cells in B and B' media 33 6. UV spectrum of authentic psilocybin -.34 6!. UV spectrum of psilocybin isolated from fungal cells 35 7. Psilocybin production from A and A' media 36 8. Psilocybin production from B and B' media 37 9. Radioautograph of chromatographed tryptophan metabolites of a mycelium extract of Psilocybe cubensis, administered D,L-tryptophan 38 10. Blue color formation when psilocybin incubated with enzyme extract 40 11. Activities of acid phosphatases of the mycelia from two different media 41 12. Chromatograms of mycelium extract and medium extract of different growth period 43 13. Tryptophan concentration of A' and B' media 48 14. Antibiotic activity of psilocin 50 15. IR spectrum of white crystals 51 16. NMR spectrum of acetate derivative of white crystals 53 17. UV spectrum of ergosterol 55 viii A SURVEY OF PHENOL-O-METHYLTRANSFERASE IN SPECIES OF LENTINUS AND LENTINELLUS 1. Radioautographs of the chromatographed methylated clnnamate products ix ACKNOWLEDGEMENT I wish to express my appreciation to Dr. G. H. N. Towers for his suggestion of this project and his advice, criticism and encouragement. I like to thank sincerely to Dr. C. K. Wat for her helpful assist• ance and guidance; to the members of committee in reading the manuscript and making critical comments; and.to the faculty, staff and students of the Department of Botany for being helpful in many ways. I also acknowledge with gratitude to Mr. Terry Q. F. Ching for his invaluable assistance in the preparation of the manuscript; to Miss Yvonne Tang for proofreading the final manuscript; and to Mr. H. P. Hsu for his contribution in many ways. X I, I. BIOLOGICAL AND BIOCHEMICAL STUDIES ON PSILOCYBE CUBENSIS 1 INTRODUCTION Intoxication, following the ingestion of certain kinds of mushrooms has. been known as early as the tenth century in the Sung Dynasty of China (69) and an 11th Century tale from Japan is about the eating of "dancing mushrooms" and "laughing mushrooms" (4, 69). Of the psychotropic materials utilized by ancient Nahuatl people of the New World, teonanacatl ("God's mushrooms" or "God's flesh") especially stands out in Mexican history (3). Since the pre-Columbian era, the Indians of Mexico have made the eating of certain fungi a part of their religious rites (15). The first record of the use of hallucinogenic mushrooms dates from 1502 at the Aztec Coronation festivals of Montezuma II (3, 70). This was recently rediscovered by R. G. Wasson and U. P. Wasson in 1957 (70). The active hallucinogenic principle was isolated from Psilocybe and therefore named psilocybin (4-phosphoryl-N,N-dimethyltryptamine). Psilocin is the dephosphorylated derivative. They are the first natural indole derivatives found to possess an OH group in position 4 and psilocybin is the first one known to contain a phosphate group (71). The chemical synthesis of these two indole alkaloids has been well 14 studied. The biosynthesis has only been studied by feeding C -labeled precursors and from these results a pathway has been proposed. Enzymological studies are meager. One of the objectives of the present study was to find better growth conditions for the production of psilocybin so as to lead to further studies on enzymology of biosynthesis and psychopharmaco- logy. Psilocybin has been demonstrated to be derived from tryptophan. An objective of this study concerned the fate of added tryptophan and of labeled tryptophan. 2 It was interesting to find out if there is any biological significance in the production of these two indole compounds. A brief examination of cultures for other obvious secondary metabolites, such as polyacetylenes, was also carried out. 3 REVIEW OF LITERATURE A. The occurrence of tryptamine derivatives in higher fungi Certain tryptamine derivatives (I) to which psychotomimetic, properties have been ascribed occur in a number of the Basidiomycetes (1, 2, 3, 4). Serotonin (II), N-methylserotonin (III), bufotenine (IV) bufotenine N-oxide (V), N,N-dimethyltryptamine (VI) and 5-methoxy-N,N- dimethyltryptamine (VII) have been found in either carpophores or mycelia of species of Amanita (Amanitaceae), Panaeolus, Coprinus (Coprinaceae), Boletus (I('B6>letaeeaeO) and Sarcodpn (Thelephoraceae) (Table 1) (5, 6, 7, 8, 9, 10). Table 1. Some Tryptamine Derivatives Found in Fungi Species Compound Amanita citrinaa.
Load more

Recommended publications
  • The Hallucinogenic Mushrooms: Diversity, Traditions, Use and Abuse with Special Reference to the Genus Psilocybe
    11 The Hallucinogenic Mushrooms: Diversity, Traditions, Use and Abuse with Special Reference to the Genus Psilocybe Gastón Guzmán Instituto de Ecologia, Km 2.5 carretera antigua a Coatepec No. 351 Congregación El Haya, Apartado postal 63, Xalapa, Veracruz 91070, Mexico E-mail: [email protected] Abstract The traditions, uses and abuses, and studies of hallucinogenic mush- rooms, mostly species of Psilocybe, are reviewed and critically analyzed. Amanita muscaria seems to be the oldest hallucinogenic mushroom used by man, although the first hallucinogenic substance, LSD, was isolated from ergot, Claviceps purpurea. Amanita muscaria is still used in North Eastern Siberia and by some North American Indians. In the past, some Mexican Indians, as well as Guatemalan Indians possibly used A. muscaria. Psilocybe has more than 150 hallucinogenic species throughout the world, but they are used in traditional ways only in Mexico and New Guinea. Some evidence suggests that a primitive tribe in the Sahara used Psilocybe in religions ceremonies centuries before Christ. New ethnomycological observations in Mexico are also described. INTRODUCTION After hallucinogenic mushrooms were discovered in Mexico in 1956-1958 by Mr. and Mrs. Wasson and Heim (Heim, 1956; Heim and Wasson, 1958; Wasson, 1957; Wasson and Wasson, 1957) and Singer and Smith (1958), a lot of attention has been devoted to them, and many publications have 257 flooded the literature (e.g. Singer, 1958a, b, 1978; Gray, 1973; Schultes, 1976; Oss and Oeric, 1976; Pollock, 1977; Ott and Bigwood, 1978; Wasson, 1980; Ammirati et al., 1985; Stamets, 1996). However, not all the fungi reported really have hallucinogenic properties, because several of them were listed by erroneous interpretation of information given by the ethnic groups originally interviewed or by the bibliography.
    [Show full text]
  • Psilocybin Mushrooms Fact Sheet
    Psilocybin Mushrooms Fact Sheet January 2017 What are psilocybin, or “magic,” mushrooms? For the next two decades thousands of doses of psilocybin were administered in clinical experiments. Psilocybin is the main ingredient found in several types Psychiatrists, scientists and mental health of psychoactive mushrooms, making it perhaps the professionals considered psychedelics like psilocybin i best-known naturally-occurring psychedelic drug. to be promising treatments as an aid to therapy for a Although psilocybin is considered active at doses broad range of psychiatric diagnoses, including around 3-4 mg, a common dose used in clinical alcoholism, schizophrenia, autism spectrum disorders, ii,iii,iv research settings ranges from 14-30 mg. Its obsessive-compulsive disorder, and depression.xiii effects on the brain are attributed to its active Many more people were also introduced to psilocybin metabolite, psilocin. Psilocybin is most commonly mushrooms and other psychedelics as part of various found in wild or homegrown mushrooms and sold religious or spiritual practices, for mental and either fresh or dried. The most popular species of emotional exploration, or to enhance wellness and psilocybin mushrooms is Psilocybe cubensis, which is creativity.xiv usually taken orally either by eating dried caps and stems or steeped in hot water and drunk as a tea, with Despite this long history and ongoing research into its v a common dose around 1-2.5 grams. therapeutic and medical benefits,xv since 1970 psilocybin and psilocin have been listed in Schedule I of the Controlled Substances Act, the most heavily Scientists and mental health professionals criminalized category for drugs considered to have a consider psychedelics like psilocybin to be “high potential for abuse” and no currently accepted promising treatments as an aid to therapy for a medical use – though when it comes to psilocybin broad range of psychiatric diagnoses.
    [Show full text]
  • Near the Himalayas, from Kashmir to Sikkim, at Altitudes the Catholic Inquisition, and the Traditional Use of These of up to 2700 Meters
    Year of edition: 2018 Authors of the text: Marc Aixalà & José Carlos Bouso Edition: Alex Verdaguer | Genís Oña | Kiko Castellanos Illustrations: Alba Teixidor EU Project: New Approaches in Harm Reduction Policies and Practices (NAHRPP) Special thanks to collaborators Alejandro Ponce (in Peyote report) and Eduardo Carchedi (in Kambó report). TECHNICAL REPORT ON PSYCHOACTIVE ETHNOBOTANICALS Volumes I - II - III ICEERS International Center for Ethnobotanical Education Research and Service INDEX SALVIA DIVINORUM 7 AMANITA MUSCARIA 13 DATURA STRAMONIUM 19 KRATOM 23 PEYOTE 29 BUFO ALVARIUS 37 PSILOCYBIN MUSHROOMS 43 IPOMOEA VIOLACEA 51 AYAHUASCA 57 IBOGA 67 KAMBÓ 73 SAN PEDRO 79 6 SALVIA DIVINORUM SALVIA DIVINORUM The effects of the Hierba Pastora have been used by Mazatec Indians since ancient times to treat diseases and for divinatory purposes. The psychoactive compound Salvia divinorum contains, Salvinorin A, is the most potent naturally occurring psychoactive substance known. BASIC INFO Ska Pastora has been used in divination and healing Salvia divinorum is a perennial plant native to the Maza- rituals, similar to psilocybin mushrooms. Maria Sabina tec areas of the Sierra Madre Oriental Mountains of Mexi- told Wasson and Hofmann (the discoverers of its Mazatec co. Its habitat is tropical forests, where it grows between usage) that Salvia divinorum was used in times when the- 300 and 800 meters above sea level. It belongs to the re was a shortage of mushrooms. Some sources that have Lamiaceae family, and is mainly reproduced by cuttings done later feldwork point out that the use of S. divinorum since it rarely produces seeds. may be more widespread than originally believed, even in times when mushrooms were abundant.
    [Show full text]
  • Mycological Investigations on Teonanacatl the Mexican Hallucinogenic Mushroom
    Mycological investigations on Teonanacatl, the mexican hallucinogenic mushroom by Rolf Singer Part I & II Mycologia, vol. 50, 1958 © Rolf Singer original report: https://mycotek.org/index.php?attachments/mycological-investigations-on-teonanacatl-the-mexian-hallucinogenic-mushroom-part-i-pdf.511 66/ Table of Contents: Part I. The history of Teonanacatl, field work and culture work 1. History 2. Field and culture work in 1957 Acknowledgments Literature cited Part II. A taxonomic monograph of psilocybe, section caerulescentes Psilocybe sect. Caerulescentes Sing., Sydowia 2: 37. 1948. Summary or the stirpes Stirps. Cubensis Stirps. Yungensis Stirps. Mexicana Stirps. Silvatica Stirps. Cyanescens Stirps. Caerulescens Stirps. Caerulipes Key to species of section Caerulescentes Stirps Cubensis Psilocybe cubensis (Earle) Sing Psilocybe subaeruginascens Höhnel Psilocybe aerugineomaculans (Höhnel) Stirps Yungensis Psilocybe yungensis Singer and Smith Stirps Mexicana Psilocybe mexicana Heim Stirps Silvatica Psilocybe silvatica (Peck) Psilocybe pelliculosa (Smith) Stirps Cyanescens Psilocybe aztecorum Heim Psilocybe cyanescens Wakefield Psilocybe collybioides Singer and Smith Description of Maire's sterile to semi-sterile material from Algeria Description of fertile material referred to Hypholoma cyanescens by Malençon Psilocybe strictipes Singer & Smith Psilocybe baeocystis Singer and Smith soma rights re-served 1 since 27.10.2016 at http://www.en.psilosophy.info/ mycological investigations on teonanacatl the mexican hallucinogenic mushroom www.en.psilosophy.info/zzvhmwgkbubhbzcmcdakcuak Stirps Caerulescens Psilocybe aggericola Singer & Smith Psilocybe candidipes Singer & Smith Psilocybe zapotecorum Heim Stirps Caerulipes Psilocybe Muliercula Singer & Smith Psilocybe caerulipes (Peck) Sacc. Literature cited soma rights re-served 2 since 27.10.2016 at http://www.en.psilosophy.info/ mycological investigations on teonanacatl the mexican hallucinogenic mushroom www.en.psilosophy.info/zzvhmwgkbubhbzcmcdakcuak Part I.
    [Show full text]
  • The Entheogen Review , Pob 19820, Sa Cramento , Ca 95819-0820, Usa  161 Vol Ume X, Number 4 Winter Solstice 2001
    VOL UME X, NUMBER 4 WINTER SOLSTICE 2001 Index Symbols Age of Entheogens & The Angels’ Dictionary, Analog Act 84, 85 The 154 Anand, Margot 67, 154 ∞Ayes 32, 49, 50, 51 age regression 89 Anderson, E.F. 106 1,4-butanediol 84 Aguaruna Indians 10 Anderson, Rocky 41 1984 155 Aguirre, G., L.E. 3, 5, 6 Anderson, Sherry 156 2001 52 Agurell, S. 57, 58, 106 Andrews, S. 86 2C-B 22, 28, 118 ahpí 7 anesthetize 21 2C-D 20 ajucá 6 angico 6 2C-I 20 Akashic record 54 angicos brancos 6 2C-T-2 20, 22, 90 Al-Queda terrorists 123 angicos pretos 6 2C-T-4 20 Alarcón, R. 5 angiquín 6 2C-T-7 20, 85, 89, 90, 94, 105, 114 Alchemind Society, The 42, 76, 112 angiquinho 6 4-acetoxy-DET 88, 89, 90, 92, 93, 96 alcohol Angraecum fragrans 86 4-acetoxy-DIPT 29, 30, 88, 90, 91, 93 38, 52, 74, 84, 98, 99, 134, 145, 146 Anon. 151 4-hydroxy-αMT 139 alcoholic beverages 86 anonymous remailer 123 4-hydroxy-DET 88, 89, 139 Aldrich 83 anthraquinones 86 4-hydroxy-DMT 88 alfalfa 129 anti-cholinergic-like central effect 150 4-hydroxy-DPT 139 alien 32, 50, 53 anti-depressant 28 5-MeO-αMT 148 alien robots 52 anti-inflammatory 86 5-MeO-DIPT 90, 94 AllChemical Arts (conference) 115 anti-marijuana laws 46 5-MeO-DMT Allen, John W. 112 anti-nausea medications 28 1, 5, 25, 84, 89, 99, 101, 102, 103, allergy preparations 28 antibacterial 135 118, 126, 148 Alli, Antero 114 antibiotic 28 5-methoxytryptamine 150 Allison 156 antidiarrheal 104 Alpert, Richard 34 antispasmatic 28 A alpha 140, 141, 142, 143, 144, 145 Antonil, André João 4 Aardvark, David α-MT 148 ants 151 α 21, 27, 28, 30, 34, 51,
    [Show full text]
  • Psychedelics: a Window to Mental Illness; Psilocybin and Depression
    Nova Southeastern University NSUWorks College of Pharmacy Student Articles College of Pharmacy 7-22-2020 Psychedelics: A Window To Mental Illness; Psilocybin And Depression Kiomary Rivera Quintana [email protected] Follow this and additional works at: https://nsuworks.nova.edu/hpd_corx_stuarticles Part of the Pharmacy and Pharmaceutical Sciences Commons Recommended Citation Rivera Quintana, Kiomary, "Psychedelics: A Window To Mental Illness; Psilocybin And Depression" (2020). College of Pharmacy Student Articles. 5. https://nsuworks.nova.edu/hpd_corx_stuarticles/5 This Literature Review is brought to you for free and open access by the College of Pharmacy at NSUWorks. It has been accepted for inclusion in College of Pharmacy Student Articles by an authorized administrator of NSUWorks. For more information, please contact [email protected]. 2020 Psychedelics: A Window to Mental Illness PSILOCYBIN AND DEPRESSION KIOMARY RIVERA QUINTANA STUDENT PHARMACIST CLASS OF 2022 PHRE 5223-DRUGS OF ABUSE NOVA SOUTHEASTERN UNIVERSITY INTRODUCTION Drug abuse is characterized by improper repeated use of drugs to seek outcomes such as pleasure, stress relief and an altered reality.1 It can lead to addiction, a severe form of substance use disorder (SUD) in which a person’s drug habits worsen and they become unable to control the impulse to use drugs despite knowing the negative consequences.1 In addition to drug seeking behavior, brain function also changes affecting the natural inhibition and reward centers. Use of and addiction to alcohol, nicotine, and illicit drugs costs the Nation more than $740 billion a year related to healthcare, crime, and lost productivity.1 Whether a person will abuse drugs or become addicted is influenced by multiple factors; the more risk factors a person has, the greater the chance.
    [Show full text]
  • <I>Psilocybe</I> from Southern China
    ISSN (print) 0093-4666 © 2014. Mycotaxon, Ltd. ISSN (online) 2154-8889 MYCOTAXON http://dx.doi.org/10.5248/129.215 Volume 129(2), pp. 215–222 October–December 2014 Morphological and molecular evidence for a new species of Psilocybe from southern China Yang-Kun Li, Ye Yuan, & Jun-Feng Liang* Research Institute of Tropical Forestry, Chinese Academy of Forestry Guangzhou, 510520, P. R. China *Correspondence to: [email protected] Abstract—Psilocybe cinnamomea sp. nov. is reported from China. It is characterized by its campanulate to plano-convex pileus, ellipsoid spores with a distinctly broad germ pore, clavate basidia, polymorphic cheilocystidia, and clavate to fusiform pleurocystidia with a short unbranched neck. Phylogenetic relationships among the new species and allied species in the genus were inferred from the internal transcribed spacer (ITS) region. Key words—Agaricales, Strophariaceae, taxonomy, phylogeny Introduction Psilocybe (Fr.) P. Kumm. was formerly a broadly circumscribed genus, including bluing, hallucinogenic species and non-bluing, non-hallucinogenic species (Guzmán 1983, Allen et al. 1992, Stamets 1996, Guzmán 2005, Borovička et al. 2011, Guzmán 2012). Recently, this broad polyphyletic genus was divided: Psilocybe sensu stricto (with P. semilanceata as its conserved type) was restricted to the bluing species, while the non-bluing species were assigned to Deconica (W.G. Sm.) P. Karst. (Redhead et al. 2007, Norvell 2010). Psilocybe s. s. contains more than 150 species worldwide (Guzmán 2005, 2009). However, only 11 species have been reported from China, of which only three were originally described from the country (Bau & Sarentoya 2009, Guzmán & Zhu L. Yang 2010, Ma et al. 2014).
    [Show full text]
  • Psychedelics in Psychiatry: Neuroplastic, Immunomodulatory, and Neurotransmitter Mechanismss
    Supplemental Material can be found at: /content/suppl/2020/12/18/73.1.202.DC1.html 1521-0081/73/1/202–277$35.00 https://doi.org/10.1124/pharmrev.120.000056 PHARMACOLOGICAL REVIEWS Pharmacol Rev 73:202–277, January 2021 Copyright © 2020 by The Author(s) This is an open access article distributed under the CC BY-NC Attribution 4.0 International license. ASSOCIATE EDITOR: MICHAEL NADER Psychedelics in Psychiatry: Neuroplastic, Immunomodulatory, and Neurotransmitter Mechanismss Antonio Inserra, Danilo De Gregorio, and Gabriella Gobbi Neurobiological Psychiatry Unit, Department of Psychiatry, McGill University, Montreal, Quebec, Canada Abstract ...................................................................................205 Significance Statement. ..................................................................205 I. Introduction . ..............................................................................205 A. Review Outline ........................................................................205 B. Psychiatric Disorders and the Need for Novel Pharmacotherapies .......................206 C. Psychedelic Compounds as Novel Therapeutics in Psychiatry: Overview and Comparison with Current Available Treatments . .....................................206 D. Classical or Serotonergic Psychedelics versus Nonclassical Psychedelics: Definition ......208 Downloaded from E. Dissociative Anesthetics................................................................209 F. Empathogens-Entactogens . ............................................................209
    [Show full text]
  • Hallucinogenic Mushrooms: a Guide
    Hallucinogenic Mushrooms: A Guide Presented by the Hamre Center for Health and Wellness Table of Contents Introduction Harm Reduction What are Hallucinogenic Mushrooms? What are the U.S. and MN Laws Surrounding Mushrooms? What Kinds of Hallucinogenic Mushrooms are There? How are Hallucinogenic Mushrooms Ingested? How Do Hallucinogenic Mushrooms Affect the Brain? What are Some Short-Term Effects of Use? What are Some Long-Term Effects of Use? How Do Hallucinogenic Mushrooms Interact with Alcohol? What are Some Harm-Reduction Strategies for Use? Are Hallucinogenic Mushrooms Addictive? What are Some Substance Abuse Help Resources? Introduction Welcome to the Hamre Center’s hallucinogenic mushrooms guide! Thank you for wanting to learn more about “magic mushrooms” and how they can affect you. This guide is designed to be a science-based resource to help inform people about hallucinogenic mushrooms. We use a harm-reduction model, which we’ll talk about more in the next slide. If you have any concerns regarding your own personal health and mushrooms, we strongly recommend that you reach out to your health care provider. No matter the legal status of hallucinogenic mushrooms in your state or country, health care providers are confidential resources. Your health is their primary concern. Harm Reduction ● The harm reduction model used in this curriculum is about neither encouraging or discouraging use; at its core, harm reduction simply aims to minimize the negative consequences of behaviors. ● Please read through the Hamre Center’s statement on use and harm reduction below: “The Hamre Center knows pleasure drives drug use, not the avoidance of harm.
    [Show full text]
  • Baeocystin in Psilocybe, Conocybe and Panaeolus
    Baeocystin in Psilocybe, Conocybe and Panaeolus DAVIDB. REPKE* P.O. Box 899, Los Altos, California 94022 and DALE THOMASLESLIE 104 Whitney Avenue, Los Gatos, California 95030 and GAST6N GUZMAN Escuela Nacional de Ciencias Biologicas, l.P.N. Apartado Postal 26-378, Mexico 4. D.F. ABSTRACT.--Sixty collections of ten species referred to three families of the Agaricales have been analyzed for the presence of baeocystin by thin-layer chro- matography. Baeocystin was detected in collections of Peilocy be, Conocy be, and Panaeolus from the U.S.A., Canada, Mexico, and Peru. Laboratory cultivated fruit- bodies of Psilocybe cubensis, P. sernilanceata, and P. cyanescens were also studied. Intra-species variation in the presence and decay rate of baeocystin, psilocybin, and psilocin are discussed in terms of age and storage factors. In addition, evidence is presented to support the presence of 4-hydroxytryptamine in collections of P. baeo- cystis and P. cyanescens. The possible significance of baeocystin and 4·hydroxy- tryptamine in the biosynthesis of psilocybin in these organisms is discussed. A recent report (1) described the isolation of baeocystin [4-phosphoryloxy-3- (2-methylaminoethyl)indole] from collections of Psilocy be semilanceata (Fr.) Kummer. Previously, baeocystin had been detected only in Psilocybe baeo- cystis Singer and Smith (2, 3). This report now describes some further obser- vations regarding the occurrence of baeocystin in species referred to three families of Agaricales. Stein, Closs, and Gabel (4) isolated a compound from an agaric that they described as Panaeolus venenosus Murr., a species which is now considered synonomous with Panaeolus subbaIteatus (Berk. and Br.) Sacco (5, 6).
    [Show full text]
  • The Production of Psilocybin in Submerged Culture by Psilocybe Cubensis
    The Production of Psilocybin in Submerged Culture by Psilocybe cubensis PHILIP CATALF01!O' AND V. E. TYLER, JR. (Drug Plant Laboratory, College of Pharmacy, University of Washington, Seattle 5) Psychotomimetic mushrooms have long been employed as intoxicants by vari- ous native peoples. Schultes (10) describes their employment in magico-religious ceremonies by the Indians of Mexico and Central America, and extensive docu- mentation of such usage has been provided by the Wassons (14, 15) and by Heim and Wasson (6). Especially noteworthy is the occurrence of certain indole derivatives in many of the basidiomycetes to which psychotomimetic properties have been ascribed. Several species of Panaeolus contain serotonin (o-hydroxytryptamine), first demonstrated in a fungus, Panaeolus campanulatus (Fr.) Quel., by Tyler (13). Bufotenine (5-hydroxy-N,lV-dimethyltryptamine) was shown to exist in Amanita citrina (Shaeff.) S. F. Gray [Amanita mappa (Lasch) Quel.] by Wieland and Motzel (16). Psilocybin (4-phosphoryl-N,N-dimethyltryptamine), together with the closely related psilocin (4-hydroxy-1Y,N-dimethyltryptamine), was first found in Psilocybe species by Hofmann, et al. (8).The latter two principles are the most recently discovered hallucinogens in basidiomycetes and are of particular interest since they are the only principles isolated from mushrooms 'w-hichare capable of inducing psychotomimetic effects in human beings following oral ingestion. Heim, et al.(7), established conditions favoring the formation of both sclerotia and sporocarps from mycelial growth obtained upon subculture of the spores and tissue of the naturally occurring Mexican Psilocybe species. In this way they obtained ample amounts of materials for isolation and structural studies of the active principles.
    [Show full text]
  • Toxic Fungi of Western North America
    Toxic Fungi of Western North America by Thomas J. Duffy, MD Published by MykoWeb (www.mykoweb.com) March, 2008 (Web) August, 2008 (PDF) 2 Toxic Fungi of Western North America Copyright © 2008 by Thomas J. Duffy & Michael G. Wood Toxic Fungi of Western North America 3 Contents Introductory Material ........................................................................................... 7 Dedication ............................................................................................................... 7 Preface .................................................................................................................... 7 Acknowledgements ................................................................................................. 7 An Introduction to Mushrooms & Mushroom Poisoning .............................. 9 Introduction and collection of specimens .............................................................. 9 General overview of mushroom poisonings ......................................................... 10 Ecology and general anatomy of fungi ................................................................ 11 Description and habitat of Amanita phalloides and Amanita ocreata .............. 14 History of Amanita ocreata and Amanita phalloides in the West ..................... 18 The classical history of Amanita phalloides and related species ....................... 20 Mushroom poisoning case registry ...................................................................... 21 “Look-Alike” mushrooms .....................................................................................
    [Show full text]