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2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads
The solid-state structure of the bufotenine derivative bis(5-methoxy-2, N , N -trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1 H -indol-3-yl)ethyl]dimethylazanium} (2 E )-but-2-enedioate), 2C 14 H 21 N 2 O + ·C 4 H 2 O 4 2− , the bufotenidine derivati...
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Published in: | Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2021-02, Vol.77 (2), p.190-194 |
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description | The solid-state structure of the bufotenine derivative bis(5-methoxy-2,
N
,
N
-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]dimethylazanium} (2
E
)-but-2-enedioate), 2C
14
H
21
N
2
O
+
·C
4
H
2
O
4
2−
, the bufotenidine derivative 5-methoxy-2,
N
,
N
,
N
-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide}, C
15
H
23
N
2
O
+
·I
−
, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C
15
H
23
N
2
O
+
·I
−
·H
2
O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked
via
N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers. |
doi_str_mv | 10.1107/S2056989021000803 |
format | article |
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N
,
N
-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]dimethylazanium} (2
E
)-but-2-enedioate), 2C
14
H
21
N
2
O
+
·C
4
H
2
O
4
2−
, the bufotenidine derivative 5-methoxy-2,
N
,
N
,
N
-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide}, C
15
H
23
N
2
O
+
·I
−
, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C
15
H
23
N
2
O
+
·I
−
·H
2
O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked
via
N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989021000803</identifier><language>eng</language><publisher>International Union of Crystallography</publisher><subject>crystal structure ; hydrogen bonds ; indoles ; tryptamines</subject><ispartof>Acta crystallographica. Section E, Crystallographic communications, 2021-02, Vol.77 (2), p.190-194</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c354t-a6c09187f02a2082b6e40f42bbf887b75cef2249462d86bec03275e5c05f1c563</citedby><cites>FETCH-LOGICAL-c354t-a6c09187f02a2082b6e40f42bbf887b75cef2249462d86bec03275e5c05f1c563</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Pham, Duyen N. K.</creatorcontrib><creatorcontrib>Chadeayne, Andrew R.</creatorcontrib><creatorcontrib>Golen, James A.</creatorcontrib><creatorcontrib>Manke, David R.</creatorcontrib><title>2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads</title><title>Acta crystallographica. Section E, Crystallographic communications</title><description>The solid-state structure of the bufotenine derivative bis(5-methoxy-2,
N
,
N
-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]dimethylazanium} (2
E
)-but-2-enedioate), 2C
14
H
21
N
2
O
+
·C
4
H
2
O
4
2−
, the bufotenidine derivative 5-methoxy-2,
N
,
N
,
N
-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide}, C
15
H
23
N
2
O
+
·I
−
, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C
15
H
23
N
2
O
+
·I
−
·H
2
O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked
via
N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.</description><subject>crystal structure</subject><subject>hydrogen bonds</subject><subject>indoles</subject><subject>tryptamines</subject><issn>2056-9890</issn><issn>2056-9890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNplkctOwzAURC0EEhX0A9j5AwjYjp0HOyivSpVYAOvoxg9wlcaV7UQqX49DEUKwuqOZuWczCJ1RckEpKS-fGRFFXdWEUUJIRfIDNJusbPIOf-ljNA9hnTqUi7wQbIY-2LnIbu1Gx_dd1w7GRd3bXmPoFZ4i9SdSKbzCvRt1h5X2doRoRx2wM7iHOHjocPS7bYRNKgZs3JBAtsc36R9DN4K3Q8DRgQqn6MhAF_T8-56g1_u7l8Vjtnp6WC6uV5nMBY8ZFJLUtCoNYcBIxdpCc2I4a1tTVWVbCqkNY7zmBVNV0WpJclYKLSQRhkpR5CdouecqB-tm6-0G_K5xYJsvw_m3Bny0stONVrVRKiHqvOaQeKwGMEyXtCyE4WVi0T1LeheC1-aHR0kzbdH82yL_BFhXfXk</recordid><startdate>20210201</startdate><enddate>20210201</enddate><creator>Pham, Duyen N. K.</creator><creator>Chadeayne, Andrew R.</creator><creator>Golen, James A.</creator><creator>Manke, David R.</creator><general>International Union of Crystallography</general><scope>AAYXX</scope><scope>CITATION</scope><scope>DOA</scope></search><sort><creationdate>20210201</creationdate><title>2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads</title><author>Pham, Duyen N. K. ; Chadeayne, Andrew R. ; Golen, James A. ; Manke, David R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c354t-a6c09187f02a2082b6e40f42bbf887b75cef2249462d86bec03275e5c05f1c563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>crystal structure</topic><topic>hydrogen bonds</topic><topic>indoles</topic><topic>tryptamines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pham, Duyen N. K.</creatorcontrib><creatorcontrib>Chadeayne, Andrew R.</creatorcontrib><creatorcontrib>Golen, James A.</creatorcontrib><creatorcontrib>Manke, David R.</creatorcontrib><collection>CrossRef</collection><collection>Directory of Open Access Journals (Open Access)</collection><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pham, Duyen N. K.</au><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>2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><date>2021-02-01</date><risdate>2021</risdate><volume>77</volume><issue>2</issue><spage>190</spage><epage>194</epage><pages>190-194</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>The solid-state structure of the bufotenine derivative bis(5-methoxy-2,
N
,
N
-trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]dimethylazanium} (2
E
)-but-2-enedioate), 2C
14
H
21
N
2
O
+
·C
4
H
2
O
4
2−
, the bufotenidine derivative 5-methoxy-2,
N
,
N
,
N
-tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide}, C
15
H
23
N
2
O
+
·I
−
, and the hydrate of the same {systematic name: [2-(5-methoxy-2-methyl-1
H
-indol-3-yl)ethyl]trimethylazanium iodide monohydrate}, C
15
H
23
N
2
O
+
·I
−
·H
2
O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N—H...O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked
via
N—H...I hydrogen bonds, and indoles are coupled in dimers through π–π interactions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water molecule in the asymmetric unit. It shows N—H...I and O—H...I hydrogen bonds that couple the tryptammonium cations into dimers.</abstract><pub>International Union of Crystallography</pub><doi>10.1107/S2056989021000803</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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language | eng |
recordid | cdi_doaj_primary_oai_doaj_org_article_ed9fddec09394a2d829aaf2e71765f47 |
source | PubMed Central (Open Access) |
subjects | crystal structure hydrogen bonds indoles tryptamines |
title | 2,5-Dimethylbufotenine and 2,5-dimethylbufotenidine: novel derivatives of natural tryptamines found in Bufo alvarius toads |
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