Loading…

Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug

The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fuma...

Full description

Saved in:
Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-06, Vol.75 (Pt 6), p.900-902
Main Authors: Chadeayne, Andrew R, Golen, James A, Manke, David R
Format: Article
Language:English
Subjects:
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c465t-8ed4e604d190f65bfd7d4fb7c7bb970e5cc4c5b01b54ea9132b70632e262e3263
cites
container_end_page 902
container_issue Pt 6
container_start_page 900
container_title Acta crystallographica. Section E, Crystallographic communications
container_volume 75
creator Chadeayne, Andrew R
Golen, James A
Manke, David R
description The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].
doi_str_mv 10.1107/S2056989019007370
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_413d3319c9c649a0a2790b31202d92e1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_413d3319c9c649a0a2790b31202d92e1</doaj_id><sourcerecordid>2270010570</sourcerecordid><originalsourceid>FETCH-LOGICAL-c465t-8ed4e604d190f65bfd7d4fb7c7bb970e5cc4c5b01b54ea9132b70632e262e3263</originalsourceid><addsrcrecordid>eNplks1u1DAQxyMEolXpA3BBPhapgbGd2GsOSFDxUamCA3C2bGeydZXEi-0U8ho8MU63VK04WPbMf-Y3M_JU1XMKrygF-fobg1aojQKqACSX8Kg6XF316nt8731QHad0BQC0ablo2dPqgFOuqFL0sPrz3qeTpjYOcx1-LzX5Qk7LqTtfj5gvl6HOcdllM45h8vP4kvTzaKLJ-IYYMuEv4uKSshkGPyHpQxxJ6Mku-WEl-umUmImYIWOcTPbXSHK4UYNbrC9KKpS9XaxdDF2ct8-qJ70ZEh7f3kfVj48fvp99ri--fjo_e3dRu0a0ud5g16CApivz96K1fSe7prfSSWuVBGyda1xrgdq2QaMoZ1aC4AyZYMiZ4EfV-Z7bBXOld9GXwRYdjNc3jhC32sTs3YC6obzjnCqnnGiUAcOkAsspA9YphrSw3u5Zu9mO2DmccjTDA-hDZfKXehuutRDtRvG1mZNbQAw_Z0xZjz45HAYzYZiTZkyWD4RWQgml-1AXQ0oR-7syFPS6Gvq_1Sg5L-73d5fxbxH4X_o1tLs</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2270010570</pqid></control><display><type>article</type><title>Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug</title><source>PubMed Central</source><creator>Chadeayne, Andrew R ; Golen, James A ; Manke, David R</creator><creatorcontrib>Chadeayne, Andrew R ; Golen, James A ; Manke, David R</creatorcontrib><description>The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989019007370</identifier><identifier>PMID: 31391991</identifier><language>eng</language><publisher>England: International Union of Crystallography</publisher><subject>crystal structure ; hydrogen bonding ; Research Communications ; tryptamines</subject><ispartof>Acta crystallographica. Section E, Crystallographic communications, 2019-06, Vol.75 (Pt 6), p.900-902</ispartof><rights>Chadeayne et al. 2019 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c465t-8ed4e604d190f65bfd7d4fb7c7bb970e5cc4c5b01b54ea9132b70632e262e3263</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658936/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658936/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27922,27923,53789,53791</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31391991$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chadeayne, Andrew R</creatorcontrib><creatorcontrib>Golen, James A</creatorcontrib><creatorcontrib>Manke, David R</creatorcontrib><title>Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug</title><title>Acta crystallographica. Section E, Crystallographic communications</title><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><description>The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].</description><subject>crystal structure</subject><subject>hydrogen bonding</subject><subject>Research Communications</subject><subject>tryptamines</subject><issn>2056-9890</issn><issn>2056-9890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNplks1u1DAQxyMEolXpA3BBPhapgbGd2GsOSFDxUamCA3C2bGeydZXEi-0U8ho8MU63VK04WPbMf-Y3M_JU1XMKrygF-fobg1aojQKqACSX8Kg6XF316nt8731QHad0BQC0ablo2dPqgFOuqFL0sPrz3qeTpjYOcx1-LzX5Qk7LqTtfj5gvl6HOcdllM45h8vP4kvTzaKLJ-IYYMuEv4uKSshkGPyHpQxxJ6Mku-WEl-umUmImYIWOcTPbXSHK4UYNbrC9KKpS9XaxdDF2ct8-qJ70ZEh7f3kfVj48fvp99ri--fjo_e3dRu0a0ud5g16CApivz96K1fSe7prfSSWuVBGyda1xrgdq2QaMoZ1aC4AyZYMiZ4EfV-Z7bBXOld9GXwRYdjNc3jhC32sTs3YC6obzjnCqnnGiUAcOkAsspA9YphrSw3u5Zu9mO2DmccjTDA-hDZfKXehuutRDtRvG1mZNbQAw_Z0xZjz45HAYzYZiTZkyWD4RWQgml-1AXQ0oR-7syFPS6Gvq_1Sg5L-73d5fxbxH4X_o1tLs</recordid><startdate>20190601</startdate><enddate>20190601</enddate><creator>Chadeayne, Andrew R</creator><creator>Golen, James A</creator><creator>Manke, David R</creator><general>International Union of Crystallography</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20190601</creationdate><title>Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug</title><author>Chadeayne, Andrew R ; Golen, James A ; Manke, David R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c465t-8ed4e604d190f65bfd7d4fb7c7bb970e5cc4c5b01b54ea9132b70632e262e3263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>crystal structure</topic><topic>hydrogen bonding</topic><topic>Research Communications</topic><topic>tryptamines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chadeayne, Andrew R</creatorcontrib><creatorcontrib>Golen, James A</creatorcontrib><creatorcontrib>Manke, David R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chadeayne, Andrew R</au><au>Golen, James A</au><au>Manke, David R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><date>2019-06-01</date><risdate>2019</risdate><volume>75</volume><issue>Pt 6</issue><spage>900</spage><epage>902</epage><pages>900-902</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H⋯O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H⋯O hydrogen bonds between the indole H atoms and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].</abstract><cop>England</cop><pub>International Union of Crystallography</pub><pmid>31391991</pmid><doi>10.1107/S2056989019007370</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2056-9890
ispartof Acta crystallographica. Section E, Crystallographic communications, 2019-06, Vol.75 (Pt 6), p.900-902
issn 2056-9890
2056-9890
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_413d3319c9c649a0a2790b31202d92e1
source PubMed Central
subjects crystal structure
hydrogen bonding
Research Communications
tryptamines
title Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T04%3A48%3A56IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Bis(4-acet-oxy-%20N%20,%20N%20-di-methyl-tryptammonium)%20fumarate:%20a%20new%20crystalline%20form%20of%20psilacetin,%20an%20alternative%20to%20psilocybin%20as%20a%20psilocin%20prodrug&rft.jtitle=Acta%20crystallographica.%20Section%20E,%20Crystallographic%20communications&rft.au=Chadeayne,%20Andrew%20R&rft.date=2019-06-01&rft.volume=75&rft.issue=Pt%206&rft.spage=900&rft.epage=902&rft.pages=900-902&rft.issn=2056-9890&rft.eissn=2056-9890&rft_id=info:doi/10.1107/S2056989019007370&rft_dat=%3Cproquest_doaj_%3E2270010570%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c465t-8ed4e604d190f65bfd7d4fb7c7bb970e5cc4c5b01b54ea9132b70632e262e3263%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2270010570&rft_id=info:pmid/31391991&rfr_iscdi=true