Psilocibin

Psilocibin
Klinički podaci
Identifikatori
CAS broj	520-52-5
ATC kod	nije dodeljen
PubChem	10624
ChemSpider	10178
KEGG	C07576
ChEMBL	CHEMBL194378
Hemijski podaci
Formula	C12H17N2O4P
Mol. masa	284,25 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17) ; Key: QVDSEJDULKLHCG-UHFFFAOYSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Zabranjena supstanca (S9) (AU) Schedule III (CA) ? (UK) Schedule I (SAD)

Psilocibin je psihodelični alkaloid iz grupe triptamina, pronađen je u psilocibinskim gljivama. Prisutan je u mnogim gljivama roda Psilocybe kao što je Psilocybe cubensis i Psilocybe semilanceata, no pronađen je i u gljivama drugih rodova. Psilocibin gljive se obično nazivaju i "magične gljive". Intenzitet i trajanje utjecaja psilocibin gljiva ovisi o vrsti gljive, dozi, individualnoj psihologiji i najviše o set i settingu.

Kemija

Psilocibin se u tijelu pretvara u farmakološki aktivni spoj psilocin defosforizacijom. Ova kemijska reakcija se događa u bazičnim uvjetima ili uz pomoć enzima fosfotaze. Psilocibin je inače i "Zwitterion" alkaloid topljiv u vodi, srednje topljiv u metanolu i etanolu i netopljiv u većini organskih otapala.

Švicarski kemičar Albert Hofmann (inače otkrivač lisergične dietilamidne kiseline) prvi je prepoznao važnost i kemijsku strukturu psilocibina i psilocina. Hofmann je dobrovoljna na sebi iskušao svojstva psilocibina.

Biologija

Psilocibin se prirodno javlja u visokim koncentracijama kod gljiva roda Psilocybe i Panaeolus, ali je pronađen u malim dozama u mnogih gljiva reda Agaricales.

Mnoge halucinogene gljive osim psilocibina sadrže i male količine njegovih analoga bacistin i norbacistin.

Mnoge psilocibin gljive poplave na prerezu ili kada su oštećene zbog oksidacije aktivnih spojeva, ipak to nije metoda za utvrđivanje gljive.

Farmakologija

Psilocibin se u tijelu brzo defosforizira u psilocin koja se onda ponaša kao selektivni agonist 5-HT_2A serotoninskog receptora u mozgu gdje oponaša funkciju serotonina (5-HT). Psilocin je agonist za 5-HT_1a i 5-HT_2A/2C.

Toksičnost

Toksičnost psilocibina je relativno mala, kada se uzme oralno kod zečeva LD₅₀ iznosi otprilike 12.5 mg/kg. U štakora, oralno, LD₅₀ je 280 mg/kg. Smrt od psilocibina u rekreacijskoj i medicinskoj uporabi nije poznata.

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

Literatura

Boire RG. (2002). Sacred Mushrooms and the Law. Berkeley, California: Ronin Publishing. ISBN 978-1579510619.
Doblin R. (1991). „Pahnke's "Good Friday Experiment": A long-term follow-up and methodological critique” (PDF). Journal of Transpersonal Psychology 23 (1): 1-25. Arhivirano iz originala na datum 2012-08-16. Pristupljeno 2014-03-30.
Marley G. (2010). „Chapter 13. Psilocybin: Gateway to the Soul or Just a Good High?”. Chanterelle Dreams, Amanita Nightmares: The Love, Lore, and Mystique of Mushrooms. White River Junction, Vermont: Chelsea Green Publishing. str. 163-84. ISBN 1-60358-214-2.
Ott J. (1993). Pharmacotheon Entheogenic Drugs Their Plant Sources and Histories. Kennewick, Washington: Natural Products Company. ISBN 978-0961423438.
Stafford PJ. (1992). Psychedelics Encyclopedia. Berkeley, California: Ronin Publishing. ISBN 0-914171-51-8.
Stamets P. (1996). Psilocybin Mushrooms of the World: An Identification Guide. Berkeley, California: Ten Speed Press. ISBN 0-89815-839-7.

2006 Džon Hopkinsovi eksperimenti

"Hopkins Scientists Show Hallucinogen in Mushrooms Creates Universal 'Mystical' Experience" Arhivirano 2011-07-30 na Wayback Machine-u, Johns Hopkins Medicine news release, July 11, 2006.
"Q&A is with Roland Griffiths, the study’s lead researcher" Arhivirano 2011-07-16 na Wayback Machine-u, Johns Hopkins Medicine news release, July 11, 2006.
"Psilocybin Viewed as Therapy or Research Tool" by Michael Smith, Medpagetoday.com, July 12, 2006.
"Magic mushrooms really cause 'spiritual' experiences" by Roxanne Khamsi, New Scientist news service, July 11, 2006.
"Drug's Mystical Properties Confirmed" by David Brown, Washington Post, July 11, 2006.
"Mushroom Drug Produces Mystical Experience", Associated Press, July 11, 2006.
"Counterculture Drug Provides Spiritual Boost" by Denise Gellene, Los Angeles Times, July 11, 2006.
"Tripping Out: Scientists Study Mystical Effects of Mushrooms" by Joy Victory, Bharathi Radhakrishnan, and Andrea Carter, ABC News (online), July 11, 2006. ABC News video report of the study.

2008 Nastavak Džon Hopkinsovih eksperimenta

"A Very Memorable Trip" Arhivirano 2009-11-13 na Wayback Machine-u, by Greg Miller, ScienceNOW Daily News, July 1, 2008
"Spiritual Effects of Hallucinogens Persist, Johns Hopkins Researchers Report" Arhivirano 2011-06-10 na Wayback Machine-u, Johns Hopkins Medicine news release, July 1, 2008.
"Psilocybin Study Hints at Rebirth of Hallucinogen Research", by Brandon Keim, "Wired," July 1, 2008
"Sacred Intentions: Inside the Johns Hopkins Psilocybin Studies" by Michael M. Hughes, Baltimore City Paper, October 8, 2008.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

Hopkins/CSP research findings and media reports, 2006, 2008, 2011 Arhivirano 2014-03-20 na Wayback Machine-u
MAPS Arhivirano 2010-10-17 na Wayback Machine-u Psilocybin research

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

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