Tentative identification of in vitro metabolites of 5-APDB, a synthetic benzofuran, by LC-Q/TOF-MS.
5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB) is a designer drug of phenethylamine and amphetamine class. In this study, the in vitro metabolism of 5-APDB was investigated in rat and human liver microsomes and human hepatocytes to characterize its metabolites. 5-APDB was incubated with microsomes or hepatocytes, and the reaction mixture was analyzed using liquid chromatography-quadrupole time-of-flight with tandem mass spectrometry (LC-Q/TOF-MS). 5-APDB was metabolized to yield three metabolites (M1, M2 and M3). These metabolites were structurally characterized on the basis of accurate mass analysis and MS/MS fragmentation patterns. Metabolite M1 and M2 were identified as hydroxylated metabolites in the benzofuran moiety; M3 was a reduced metabolite which may be generated from M1 or M2 via dehydration. These results provide evidence for the in vivo 5-APDB metabolism, and would be forensically useful for the detection of 5-APDB and its metabolites in biological samples.
Institute of Pharmaceutical Science and Technology and College of Pharmacy, Hanyang University, Ansan, Gyeonggi-do, Republic of Korea.
Jong Suk
JS
Park
Institute of Pharmaceutical Science and Technology and College of Pharmacy, Hanyang University, Ansan, Gyeonggi-do, Republic of Korea.
Shaheed Ur
SU
Rehman
Institute of Pharmaceutical Science and Technology and College of Pharmacy, Hanyang University, Ansan, Gyeonggi-do, Republic of Korea.
In Sook
IS
Kim
Institute of Pharmaceutical Science and Technology and College of Pharmacy, Hanyang University, Ansan, Gyeonggi-do, Republic of Korea.
Min Sun
MS
Choi
Drug and Forensic Toxicology Division, National Forensic Service, Wonju, Republic of Korea.
Jae Sin
JS
Lee
Drug and Forensic Toxicology Division, National Forensic Service, Wonju, Republic of Korea.
Sanghwan
S
In
Institute of Pharmaceutical Science and Technology and College of Pharmacy, Hanyang University, Ansan, Gyeonggi-do, Republic of Korea. Electronic address: yoohh@hanyang.ac.kr.
Hye Hyun
HH
Yoo
D000818:Animals; D001572:Benzofurans / Q000378:metabolism*; D002853:Chromatography, Liquid / Q000379:methods*; D022781:Hepatocytes / Q000378:metabolism; D006801:Humans; D053858:Metabolic Networks and Pathways; D008862:Microsomes, Liver / Q000378:metabolism; D051381:Rats; D053719:Tandem Mass Spectrometry / Q000379:methods*
D001572:Benzofurans; C084475:5-(aminopropyl)-2,3-dihydrobenzofuran
5-APDB; Designer drug; LC-Q/TOF-MS; Metabolite