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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...
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Published in: | Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-06, Vol.75 (Pt 6), p.900-902 |
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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 |
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-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> |
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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 |
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