{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,31]],"date-time":"2026-01-31T09:42:14Z","timestamp":1769852534756,"version":"3.49.0"},"reference-count":15,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2015,11,23]],"date-time":"2015-11-23T00:00:00Z","timestamp":1448236800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2017,3]]},"abstract":"<jats:p>Two significant compounds often found in the gas chromatographic analysis of the acid\/neutral extracts from illicit heroin have remained uncharacterized for 30\u2009years. The unknown compounds are referred to as the \u2018B\u2019 and \u2018C\u2019 compounds. It has been postulated that these compounds arise from acetylation of porphyroxine, a rhoeadine alkaloid found at trace levels in the opium poppy, <jats:italic>Papaver somniferum<\/jats:italic>. Porphyroxine was isolated from opium and acetylated to produce N,O<jats:sup>8<\/jats:sup>\u2010diacetylporphyroxine. Mild hydrolysis produced N,O<jats:sup>8<\/jats:sup>\u2010diacetyl\u2010O<jats:sup>14<\/jats:sup>\u2010desmethyl\u2010<jats:italic>epi<\/jats:italic>\u2010porphyroxine (the C compound) and N\u2010acetyl\u2010O<jats:sup>14<\/jats:sup>\u2010desmethyl\u2010<jats:italic>epi<\/jats:italic>\u2010porphyroxine (the B compound). Both N,O<jats:sup>8<\/jats:sup>\u2010diacetyl\u2010O<jats:sup>14<\/jats:sup>\u2010desmethyl\u2010<jats:italic>epi<\/jats:italic>\u2010porphyroxine and N\u2010acetyl\u2010O<jats:sup>14<\/jats:sup>\u2010desmethyl\u2010<jats:italic>epi<\/jats:italic>\u2010porphyroxine were determined to be C\u201014 epimers of porphyroxine and N,O<jats:sup>8<\/jats:sup>\u2010diacetylporphyroxine. The non\u2010epimerized isomers of the B and C compounds were also detected in illicit heroin, but at much lower levels. Chromatographic and spectroscopic data are presented for the aforementioned compounds. The presence\/absence and relative concentrations of these compounds is presented for the four types of heroin (Southwest Asian, South American, Southeast Asian, and Mexican). The prevalence of detection for the B and C compounds are Southwest Asian\u2009=\u200992\u201093%, South American\u2009=\u200964\u201072%, Southeast Asian\u2009=\u200945\u201049%, and Mexican\u2009<jats:styled-content>\u2264<\/jats:styled-content>\u20093%. When detected, the overall trend of relative concentrations of dicaetylporhyroxine, the B\u2010compound, and C\u2010compound is Southwest Asian\u2009&gt;\u2009South American\u2009&gt;\u2009Southeast Asian, each by an order of magnitude. These compounds were rarely detected in Mexican heroin. The presence\/absence and relative concentrations of these compounds provide pertinent forensic signature characteristics that significantly enhance the final regional classifications. Copyright \u00a9 2015 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/dta.1922","type":"journal-article","created":{"date-parts":[[2015,11,23]],"date-time":"2015-11-23T03:33:53Z","timestamp":1448249633000},"page":"462-469","source":"Crossref","is-referenced-by-count":7,"title":["Characterization and origin of the \u2018B\u2019 and \u2018C\u2019 compounds in the acid\/neutral forensic signatures of heroin \u2013 products from the acylation of porphyroxine and subsequent hydrolysis"],"prefix":"10.1002","volume":"9","author":[{"given":"John F.","family":"Casale","sequence":"first","affiliation":[{"name":"Special Testing and Research Laboratory U.S. Drug Enforcement Administration  22624 Dulles Summit Court Dulles VA 20166\u20109509 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ellen S.","family":"Casale","sequence":"additional","affiliation":[{"name":"Special Testing and Research Laboratory U.S. Drug Enforcement Administration  22624 Dulles Summit Court Dulles VA 20166\u20109509 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Steven G.","family":"Toske","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Patrick A.","family":"Hays","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sini","family":"Panicker","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,11,23]]},"reference":[{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1556-4029.2009.01220.x"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1556-4029.2006.00057.x"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0379-0738(94)90043-4"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/b009093j"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-0738(96)02086-5"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1556-4029.2006.00122.x"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-0738(00)00295-4"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-0738(01)00541-2"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-0738(98)00081-4"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/0379-0738(88)90083-7"},{"key":"e_1_2_5_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18370210214"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.2042-7158.1963.tb12771.x"},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600561226"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50028a001"},{"key":"e_1_2_5_16_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac197125030527"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.1922","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fdta.1922","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.1922","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T08:56:15Z","timestamp":1760345775000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.1922"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,11,23]]},"references-count":15,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2017,3]]}},"alternative-id":["10.1002\/dta.1922"],"URL":"https:\/\/doi.org\/10.1002\/dta.1922","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,11,23]]}}}