Metabolic Profile Determination of NBOMe Compounds Using Human Liver Microsomes and Comparison with Findings in Authentic Human Blood and Urine.
Identifieur interne : 000963 ( Main/Corpus ); précédent : 000962; suivant : 000964Metabolic Profile Determination of NBOMe Compounds Using Human Liver Microsomes and Comparison with Findings in Authentic Human Blood and Urine.
Auteurs : Keith-Dane H. Temporal ; Karen S. Scott ; Amanda L A. Mohr ; Barry K. LoganSource :
- Journal of analytical toxicology [ 1945-2403 ] ; 2017.
English descriptors
- KwdEn :
- Designer Drugs (metabolism), Hallucinogens (blood), Hallucinogens (metabolism), Hallucinogens (urine), Humans (MeSH), Illicit Drugs (blood), Illicit Drugs (metabolism), Illicit Drugs (urine), Metabolome (physiology), Microsomes, Liver (metabolism), Phenethylamines (analysis), Phenethylamines (blood), Phenethylamines (metabolism), Phenethylamines (urine), Substance Abuse Detection (methods).
- MESH :
- chemical , analysis : Phenethylamines.
- chemical , blood : Hallucinogens, Illicit Drugs, Phenethylamines.
- chemical , metabolism : Designer Drugs, Hallucinogens, Illicit Drugs, Phenethylamines.
- chemical , urine : Hallucinogens, Illicit Drugs, Phenethylamines.
- metabolism : Microsomes, Liver.
- methods : Substance Abuse Detection.
- physiology : Metabolome.
- Humans.
Abstract
The emergence of novel psychoactive substances (NPS) such as hallucinogenic NBOMes (N-methoxybenzyl derivatives of 2C phenethylamines) in the past few years into the recreational drug market has introduced various challenges in forensic analytical toxicology in regard to adequate and timely detection of these compounds. This is especially true in samples from individuals who have experienced severe and fatal intoxications. The aim of this research was to identify the major Phase I metabolites of selected NBOMe compounds to generate a predicted human metabolic pathway of these substances. An in vitro incubation method of pooled human liver microsomes (HLMs) with four (4) NBOMes was used to identify major metabolites. These metabolic products were identified and confirmed from accurate mass findings of samples analyzed by Ultra Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry. The most common biotransformations observed among this group of NBOMes include O-demethylations at the three methoxy groups, hydroxylations and reduction at the amine group. Other metabolic products observed include positional isomers from various hydroxylation possibilities on the benzene ring and alkyl chains, and secondary metabolism resulting in multiple combinations of the reactions. Many of the major metabolites were subsequently identified in authentic human samples of blood and urine from drug users.
DOI: 10.1093/jat/bkx029
PubMed: 28472358
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Mohr</name><affiliation><nlm:affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Logan, Barry K" sort="Logan, Barry K" uniqKey="Logan B" first="Barry K" last="Logan">Barry K. Logan</name><affiliation><nlm:affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</nlm:affiliation></affiliation><affiliation><nlm:affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation><affiliation><nlm:affiliation>NMS Labs, 3701 Welsh Road, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2017">2017</date><idno type="RBID">pubmed:28472358</idno><idno type="pmid">28472358</idno><idno type="doi">10.1093/jat/bkx029</idno><idno type="wicri:Area/Main/Corpus">000963</idno><idno type="wicri:explorRef" wicri:stream="Main" wicri:step="Corpus" wicri:corpus="PubMed">000963</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Metabolic Profile Determination of NBOMe Compounds Using Human Liver Microsomes and Comparison with Findings in Authentic Human Blood and Urine.</title><author><name sortKey="Temporal, Keith Dane H" sort="Temporal, Keith Dane H" uniqKey="Temporal K" first="Keith-Dane H" last="Temporal">Keith-Dane H. Temporal</name><affiliation><nlm:affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Scott, Karen S" sort="Scott, Karen S" uniqKey="Scott K" first="Karen S" last="Scott">Karen S. Scott</name><affiliation><nlm:affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Mohr, Amanda L A" sort="Mohr, Amanda L A" uniqKey="Mohr A" first="Amanda L A" last="Mohr">Amanda L A. Mohr</name><affiliation><nlm:affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Logan, Barry K" sort="Logan, Barry K" uniqKey="Logan B" first="Barry K" last="Logan">Barry K. Logan</name><affiliation><nlm:affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</nlm:affiliation></affiliation><affiliation><nlm:affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation><affiliation><nlm:affiliation>NMS Labs, 3701 Welsh Road, Willow Grove, PA 19090, USA.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Journal of analytical toxicology</title><idno type="eISSN">1945-2403</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Designer Drugs (metabolism)</term><term>Hallucinogens (blood)</term><term>Hallucinogens (metabolism)</term><term>Hallucinogens (urine)</term><term>Humans (MeSH)</term><term>Illicit Drugs (blood)</term><term>Illicit Drugs (metabolism)</term><term>Illicit Drugs (urine)</term><term>Metabolome (physiology)</term><term>Microsomes, Liver (metabolism)</term><term>Phenethylamines (analysis)</term><term>Phenethylamines (blood)</term><term>Phenethylamines (metabolism)</term><term>Phenethylamines (urine)</term><term>Substance Abuse Detection (methods)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Phenethylamines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="blood" xml:lang="en"><term>Hallucinogens</term><term>Illicit Drugs</term><term>Phenethylamines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Designer Drugs</term><term>Hallucinogens</term><term>Illicit Drugs</term><term>Phenethylamines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="urine" xml:lang="en"><term>Hallucinogens</term><term>Illicit Drugs</term><term>Phenethylamines</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Microsomes, Liver</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Substance Abuse Detection</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Metabolome</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Humans</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The emergence of novel psychoactive substances (NPS) such as hallucinogenic NBOMes (N-methoxybenzyl derivatives of 2C phenethylamines) in the past few years into the recreational drug market has introduced various challenges in forensic analytical toxicology in regard to adequate and timely detection of these compounds. This is especially true in samples from individuals who have experienced severe and fatal intoxications. The aim of this research was to identify the major Phase I metabolites of selected NBOMe compounds to generate a predicted human metabolic pathway of these substances. An in vitro incubation method of pooled human liver microsomes (HLMs) with four (4) NBOMes was used to identify major metabolites. These metabolic products were identified and confirmed from accurate mass findings of samples analyzed by Ultra Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry. The most common biotransformations observed among this group of NBOMes include O-demethylations at the three methoxy groups, hydroxylations and reduction at the amine group. Other metabolic products observed include positional isomers from various hydroxylation possibilities on the benzene ring and alkyl chains, and secondary metabolism resulting in multiple combinations of the reactions. Many of the major metabolites were subsequently identified in authentic human samples of blood and urine from drug users.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28472358</PMID><DateCompleted><Year>2017</Year><Month>12</Month><Day>20</Day></DateCompleted><DateRevised><Year>2019</Year><Month>12</Month><Day>10</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1945-2403</ISSN><JournalIssue CitedMedium="Internet"><Volume>41</Volume><Issue>7</Issue><PubDate><Year>2017</Year><Month>Sep</Month><Day>01</Day></PubDate></JournalIssue><Title>Journal of analytical toxicology</Title><ISOAbbreviation>J Anal Toxicol</ISOAbbreviation></Journal><ArticleTitle>Metabolic Profile Determination of NBOMe Compounds Using Human Liver Microsomes and Comparison with Findings in Authentic Human Blood and Urine.</ArticleTitle><Pagination><MedlinePgn>646-657</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1093/jat/bkx029</ELocationID><Abstract><AbstractText>The emergence of novel psychoactive substances (NPS) such as hallucinogenic NBOMes (N-methoxybenzyl derivatives of 2C phenethylamines) in the past few years into the recreational drug market has introduced various challenges in forensic analytical toxicology in regard to adequate and timely detection of these compounds. This is especially true in samples from individuals who have experienced severe and fatal intoxications. The aim of this research was to identify the major Phase I metabolites of selected NBOMe compounds to generate a predicted human metabolic pathway of these substances. An in vitro incubation method of pooled human liver microsomes (HLMs) with four (4) NBOMes was used to identify major metabolites. These metabolic products were identified and confirmed from accurate mass findings of samples analyzed by Ultra Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry. The most common biotransformations observed among this group of NBOMes include O-demethylations at the three methoxy groups, hydroxylations and reduction at the amine group. Other metabolic products observed include positional isomers from various hydroxylation possibilities on the benzene ring and alkyl chains, and secondary metabolism resulting in multiple combinations of the reactions. Many of the major metabolites were subsequently identified in authentic human samples of blood and urine from drug users.</AbstractText><CopyrightInformation>© The Author 2017. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Temporal</LastName><ForeName>Keith-Dane H</ForeName><Initials>KH</Initials><AffiliationInfo><Affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Scott</LastName><ForeName>Karen S</ForeName><Initials>KS</Initials><AffiliationInfo><Affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Mohr</LastName><ForeName>Amanda L A</ForeName><Initials>ALA</Initials><AffiliationInfo><Affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Logan</LastName><ForeName>Barry K</ForeName><Initials>BK</Initials><AffiliationInfo><Affiliation>Arcadia University, 450 S. Easton Road, Glenside, PA 19038, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>The Center for Forensic Science Research and Education, 2300 Stratford Avenue, Willow Grove, PA 19090, USA.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>NMS Labs, 3701 Welsh Road, Willow Grove, PA 19090, USA.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>J Anal Toxicol</MedlineTA><NlmUniqueID>7705085</NlmUniqueID><ISSNLinking>0146-4760</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D015198">Designer Drugs</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D006213">Hallucinogens</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013287">Illicit Drugs</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010627">Phenethylamines</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D015198" MajorTopicYN="N">Designer Drugs</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006213" MajorTopicYN="N">Hallucinogens</DescriptorName><QualifierName UI="Q000097" MajorTopicYN="N">blood</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000652" MajorTopicYN="N">urine</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013287" MajorTopicYN="N">Illicit Drugs</DescriptorName><QualifierName UI="Q000097" MajorTopicYN="N">blood</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000652" MajorTopicYN="N">urine</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D055442" MajorTopicYN="N">Metabolome</DescriptorName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008862" MajorTopicYN="N">Microsomes, Liver</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010627" MajorTopicYN="N">Phenethylamines</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="N">analysis</QualifierName><QualifierName UI="Q000097" MajorTopicYN="N">blood</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000652" MajorTopicYN="N">urine</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015813" MajorTopicYN="N">Substance Abuse Detection</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="N">methods</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>08</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2017</Year><Month>5</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>12</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2017</Year><Month>5</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">28472358</ArticleId><ArticleId IdType="pii">3793129</ArticleId><ArticleId IdType="doi">10.1093/jat/bkx029</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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