Photocyclizations of pharmacodynamic amines. III. Three-dimensional structure of 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one from mescaline

The three-dimensional structure of a photocyclization product derived from mescaline, 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one, was determined by X-ray crystallography. The molecule contains a bicyclic ring system with an azabicyclo[5.2.2]undecane framework, including a ketone and hydroxyl group, and three methoxy substituents. The configuration confirms the stereochemistry resulting from the photochemical reaction of mescaline, a pharmacodynamic amine. This structural elucidation provides insight into the reaction pathway and the three-dimensional arrangement of atoms in the product.

Study at a glance

Abstract

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPhotocyclizations of pharmacodynamic amines. III. Three-dimensional structure of 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one from mescalineOsamu Yonemitsu, H. Nakai, Yuichi Kanaoka, Isabella L. Karle, and Bernhard WitkopCite this: J. Am. Chem. Soc. 1969, 91, 16, 4591–4593Publication Date (Print):July 1, 1969Publication History Published online1 May 2002Published inissue 1 July 1969https://pubs.acs.org/doi/10.1021/ja01044a071https://doi.org/10.1021/ja01044a071research-articleACS PublicationsRequest reuse permissionsArticle Views69Altmetric-Citations12LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts