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Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors
The title compound, 4-hy-droxy- -iso-propyl-tryptamine ( ) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1 -indol-4-ol), C H N O, was synthesized in three steps from 4-benzyl-oxyindole ( ) (systematic name: 4-phen-oxy-1 -indole), C H NO. ( ) was treated with oxalyl chloride and is...
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Published in: | Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-03, Vol.79 (Pt 4), p.280-286 |
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container_end_page | 286 |
container_issue | Pt 4 |
container_start_page | 280 |
container_title | Acta crystallographica. Section E, Crystallographic communications |
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creator | Laban, Uroš Naeem, Marilyn Chadeayne, Andrew R Golen, James A Manke, David R |
description | The title compound, 4-hy-droxy-
-iso-propyl-tryptamine (
) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1
-indol-4-ol), C
H
N
O, was synthesized in three steps from 4-benzyl-oxyindole (
) (systematic name: 4-phen-oxy-1
-indole), C
H
NO. (
) was treated with oxalyl chloride and iso-propyl-amine to produce
-isopropyl-4-benz-yloxy-3-indole-glyoxyl-amide (
) {systematic name: 2-[4-(benz-yloxy)-1
-indol-3-yl]-2-oxo-
-(propan-2-yl)acet-amide}, C
H
N
O
. (
) was reduced to generate 4-benz-yloxy-
-iso-propyl-tryptamine
or 4-HO-NiPT, which was characterized as its chloride salt 4-benz-yloxy-
-iso-propyl-tryptammonium chloride (
) (systematic name: {2-[4-(benz-yloxy)-1
-indol-3-yl]eth-yl}(propan-2-yl)aza-nium chloride), C
H
N
O·Cl. Finally the benzyl group of
was removed
hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented. |
doi_str_mv | 10.1107/S2056989023002098 |
format | article |
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-iso-propyl-tryptamine (
) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1
-indol-4-ol), C
H
N
O, was synthesized in three steps from 4-benzyl-oxyindole (
) (systematic name: 4-phen-oxy-1
-indole), C
H
NO. (
) was treated with oxalyl chloride and iso-propyl-amine to produce
-isopropyl-4-benz-yloxy-3-indole-glyoxyl-amide (
) {systematic name: 2-[4-(benz-yloxy)-1
-indol-3-yl]-2-oxo-
-(propan-2-yl)acet-amide}, C
H
N
O
. (
) was reduced to generate 4-benz-yloxy-
-iso-propyl-tryptamine
or 4-HO-NiPT, which was characterized as its chloride salt 4-benz-yloxy-
-iso-propyl-tryptammonium chloride (
) (systematic name: {2-[4-(benz-yloxy)-1
-indol-3-yl]eth-yl}(propan-2-yl)aza-nium chloride), C
H
N
O·Cl. Finally the benzyl group of
was removed
hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989023002098</identifier><identifier>PMID: 37057027</identifier><language>eng</language><publisher>England: International Union of Crystallography</publisher><subject>Research Communications</subject><ispartof>Acta crystallographica. Section E, Crystallographic communications, 2023-03, Vol.79 (Pt 4), p.280-286</ispartof><rights>Laban et al. 2023.</rights><rights>Laban et al. 2023 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0009-0000-6351-9262 ; 0000-0002-2513-4801 ; 0000-0003-0449-0337 ; 0000-0002-6615-1253</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088304/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10088304/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37057027$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Laban, Uroš</creatorcontrib><creatorcontrib>Naeem, Marilyn</creatorcontrib><creatorcontrib>Chadeayne, Andrew R</creatorcontrib><creatorcontrib>Golen, James A</creatorcontrib><creatorcontrib>Manke, David R</creatorcontrib><title>Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors</title><title>Acta crystallographica. Section E, Crystallographic communications</title><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><description>The title compound, 4-hy-droxy-
-iso-propyl-tryptamine (
) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1
-indol-4-ol), C
H
N
O, was synthesized in three steps from 4-benzyl-oxyindole (
) (systematic name: 4-phen-oxy-1
-indole), C
H
NO. (
) was treated with oxalyl chloride and iso-propyl-amine to produce
-isopropyl-4-benz-yloxy-3-indole-glyoxyl-amide (
) {systematic name: 2-[4-(benz-yloxy)-1
-indol-3-yl]-2-oxo-
-(propan-2-yl)acet-amide}, C
H
N
O
. (
) was reduced to generate 4-benz-yloxy-
-iso-propyl-tryptamine
or 4-HO-NiPT, which was characterized as its chloride salt 4-benz-yloxy-
-iso-propyl-tryptammonium chloride (
) (systematic name: {2-[4-(benz-yloxy)-1
-indol-3-yl]eth-yl}(propan-2-yl)aza-nium chloride), C
H
N
O·Cl. Finally the benzyl group of
was removed
hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.</description><subject>Research Communications</subject><issn>2056-9890</issn><issn>2056-9890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpVkFFLwzAUhYMobsz9AF-kj_MhepM0TfMkMtQJYxM2Xy1Zm7hI19SkFfvv3XTKfLqHcy_fOVyEzglcEQLiekGBJzKVQBkABZkeof7Owjvv-ED30DCENwAgMWcJp6eoxwRwAVT00cuiq5q1DjZEqiqi0Pg2b1qvI2eiGK87XHj32eFoFmEbHK69q7sSN76rG7WxlY5GMZ7M8cw-LS-_CbYJUe113vrgfDhDJ0aVQQ_3c4Ce7--W4wmezh8ex7dTXBNCY5ynisuEMmGY0JKrIjE6JoKlRCVa5BwkEJPnsRFkVSRCSWakXHGTsFgrrQo2QDc_3LpdbXSR66rxqsxqbzfKd5lTNvu_qew6e3UfGQFIUwbxljDaE7x7b3Voso0NuS5LVWnXhoymQKRItpW2pxeHYX8pv19lX7BSevc</recordid><startdate>20230301</startdate><enddate>20230301</enddate><creator>Laban, Uroš</creator><creator>Naeem, Marilyn</creator><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>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0009-0000-6351-9262</orcidid><orcidid>https://orcid.org/0000-0002-2513-4801</orcidid><orcidid>https://orcid.org/0000-0003-0449-0337</orcidid><orcidid>https://orcid.org/0000-0002-6615-1253</orcidid></search><sort><creationdate>20230301</creationdate><title>Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors</title><author>Laban, Uroš ; Naeem, Marilyn ; Chadeayne, Andrew R ; Golen, James A ; Manke, David R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p1124-c8a596237f37e95ad6fe417381a6e7c50901fcc4f71bd67a93f99b5f634eaead3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Research Communications</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Laban, Uroš</creatorcontrib><creatorcontrib>Naeem, Marilyn</creatorcontrib><creatorcontrib>Chadeayne, Andrew R</creatorcontrib><creatorcontrib>Golen, James A</creatorcontrib><creatorcontrib>Manke, David R</creatorcontrib><collection>PubMed</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Laban, Uroš</au><au>Naeem, Marilyn</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>Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><addtitle>Acta Crystallogr E Crystallogr Commun</addtitle><date>2023-03-01</date><risdate>2023</risdate><volume>79</volume><issue>Pt 4</issue><spage>280</spage><epage>286</epage><pages>280-286</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>The title compound, 4-hy-droxy-
-iso-propyl-tryptamine (
) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1
-indol-4-ol), C
H
N
O, was synthesized in three steps from 4-benzyl-oxyindole (
) (systematic name: 4-phen-oxy-1
-indole), C
H
NO. (
) was treated with oxalyl chloride and iso-propyl-amine to produce
-isopropyl-4-benz-yloxy-3-indole-glyoxyl-amide (
) {systematic name: 2-[4-(benz-yloxy)-1
-indol-3-yl]-2-oxo-
-(propan-2-yl)acet-amide}, C
H
N
O
. (
) was reduced to generate 4-benz-yloxy-
-iso-propyl-tryptamine
or 4-HO-NiPT, which was characterized as its chloride salt 4-benz-yloxy-
-iso-propyl-tryptammonium chloride (
) (systematic name: {2-[4-(benz-yloxy)-1
-indol-3-yl]eth-yl}(propan-2-yl)aza-nium chloride), C
H
N
O·Cl. Finally the benzyl group of
was removed
hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.</abstract><cop>England</cop><pub>International Union of Crystallography</pub><pmid>37057027</pmid><doi>10.1107/S2056989023002098</doi><tpages>7</tpages><orcidid>https://orcid.org/0009-0000-6351-9262</orcidid><orcidid>https://orcid.org/0000-0002-2513-4801</orcidid><orcidid>https://orcid.org/0000-0003-0449-0337</orcidid><orcidid>https://orcid.org/0000-0002-6615-1253</orcidid><oa>free_for_read</oa></addata></record> |
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language | eng |
recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_10088304 |
source | PubMed Central |
subjects | Research Communications |
title | Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors |
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