Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs

Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to oth...
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Autor*in:	Eric Sparkes [verfasserIn] Rochelle Boyd [verfasserIn] Shuli Chen [verfasserIn] Jack W. Markham [verfasserIn] Jia Lin Luo [verfasserIn] Tahira Foyzun [verfasserIn] Humayra Zaman [verfasserIn] Charlotte Fletcher [verfasserIn] Ross Ellison [verfasserIn] Iain S. McGregor [verfasserIn] Marina J. Santiago [verfasserIn] Felcia Lai [verfasserIn] Roy R. Gerona [verfasserIn] Mark Connor [verfasserIn] David E. Hibbs [verfasserIn] Elizabeth A. Cairns [verfasserIn] Michelle Glass [verfasserIn] Adam Ametovski [verfasserIn] Samuel D. Banister [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking

Übergeordnetes Werk:	In: Frontiers in Psychiatry - Frontiers Media S.A., 2010, 13(2022)
Übergeordnetes Werk:	volume:13 ; year:2022

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3389/fpsyt.2022.1010501

Katalog-ID:	DOAJ022902724

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245	1	0	\|a Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
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allfields	10.3389/fpsyt.2022.1010501 doi (DE-627)DOAJ022902724 (DE-599)DOAJ8bb387539a3c4fa38d68649acedf0eb4 DE-627 ger DE-627 rakwb eng RC435-571 Eric Sparkes verfasserin aut Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity. synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry Eric Sparkes verfasserin aut Rochelle Boyd verfasserin aut Rochelle Boyd verfasserin aut Shuli Chen verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jia Lin Luo verfasserin aut Jia Lin Luo verfasserin aut Tahira Foyzun verfasserin aut Humayra Zaman verfasserin aut Charlotte Fletcher verfasserin aut Charlotte Fletcher verfasserin aut Ross Ellison verfasserin aut Iain S. McGregor verfasserin aut Iain S. McGregor verfasserin aut Marina J. Santiago verfasserin aut Felcia Lai verfasserin aut Roy R. Gerona verfasserin aut Mark Connor verfasserin aut David E. Hibbs verfasserin aut Elizabeth A. Cairns verfasserin aut Elizabeth A. Cairns verfasserin aut Michelle Glass verfasserin aut Adam Ametovski verfasserin aut Adam Ametovski verfasserin aut Samuel D. Banister verfasserin aut Samuel D. Banister verfasserin aut In Frontiers in Psychiatry Frontiers Media S.A., 2010 13(2022) (DE-627)631498796 (DE-600)2564218-2 16640640 nnns volume:13 year:2022 https://doi.org/10.3389/fpsyt.2022.1010501 kostenfrei https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 kostenfrei https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full kostenfrei https://doaj.org/toc/1664-0640 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 13 2022
spelling	10.3389/fpsyt.2022.1010501 doi (DE-627)DOAJ022902724 (DE-599)DOAJ8bb387539a3c4fa38d68649acedf0eb4 DE-627 ger DE-627 rakwb eng RC435-571 Eric Sparkes verfasserin aut Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity. synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry Eric Sparkes verfasserin aut Rochelle Boyd verfasserin aut Rochelle Boyd verfasserin aut Shuli Chen verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jia Lin Luo verfasserin aut Jia Lin Luo verfasserin aut Tahira Foyzun verfasserin aut Humayra Zaman verfasserin aut Charlotte Fletcher verfasserin aut Charlotte Fletcher verfasserin aut Ross Ellison verfasserin aut Iain S. McGregor verfasserin aut Iain S. McGregor verfasserin aut Marina J. Santiago verfasserin aut Felcia Lai verfasserin aut Roy R. Gerona verfasserin aut Mark Connor verfasserin aut David E. Hibbs verfasserin aut Elizabeth A. Cairns verfasserin aut Elizabeth A. Cairns verfasserin aut Michelle Glass verfasserin aut Adam Ametovski verfasserin aut Adam Ametovski verfasserin aut Samuel D. Banister verfasserin aut Samuel D. Banister verfasserin aut In Frontiers in Psychiatry Frontiers Media S.A., 2010 13(2022) (DE-627)631498796 (DE-600)2564218-2 16640640 nnns volume:13 year:2022 https://doi.org/10.3389/fpsyt.2022.1010501 kostenfrei https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 kostenfrei https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full kostenfrei https://doaj.org/toc/1664-0640 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 13 2022
allfields_unstemmed	10.3389/fpsyt.2022.1010501 doi (DE-627)DOAJ022902724 (DE-599)DOAJ8bb387539a3c4fa38d68649acedf0eb4 DE-627 ger DE-627 rakwb eng RC435-571 Eric Sparkes verfasserin aut Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity. synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry Eric Sparkes verfasserin aut Rochelle Boyd verfasserin aut Rochelle Boyd verfasserin aut Shuli Chen verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jia Lin Luo verfasserin aut Jia Lin Luo verfasserin aut Tahira Foyzun verfasserin aut Humayra Zaman verfasserin aut Charlotte Fletcher verfasserin aut Charlotte Fletcher verfasserin aut Ross Ellison verfasserin aut Iain S. McGregor verfasserin aut Iain S. McGregor verfasserin aut Marina J. Santiago verfasserin aut Felcia Lai verfasserin aut Roy R. Gerona verfasserin aut Mark Connor verfasserin aut David E. Hibbs verfasserin aut Elizabeth A. Cairns verfasserin aut Elizabeth A. Cairns verfasserin aut Michelle Glass verfasserin aut Adam Ametovski verfasserin aut Adam Ametovski verfasserin aut Samuel D. Banister verfasserin aut Samuel D. Banister verfasserin aut In Frontiers in Psychiatry Frontiers Media S.A., 2010 13(2022) (DE-627)631498796 (DE-600)2564218-2 16640640 nnns volume:13 year:2022 https://doi.org/10.3389/fpsyt.2022.1010501 kostenfrei https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 kostenfrei https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full kostenfrei https://doaj.org/toc/1664-0640 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 13 2022
allfieldsGer	10.3389/fpsyt.2022.1010501 doi (DE-627)DOAJ022902724 (DE-599)DOAJ8bb387539a3c4fa38d68649acedf0eb4 DE-627 ger DE-627 rakwb eng RC435-571 Eric Sparkes verfasserin aut Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity. synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry Eric Sparkes verfasserin aut Rochelle Boyd verfasserin aut Rochelle Boyd verfasserin aut Shuli Chen verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jia Lin Luo verfasserin aut Jia Lin Luo verfasserin aut Tahira Foyzun verfasserin aut Humayra Zaman verfasserin aut Charlotte Fletcher verfasserin aut Charlotte Fletcher verfasserin aut Ross Ellison verfasserin aut Iain S. McGregor verfasserin aut Iain S. McGregor verfasserin aut Marina J. Santiago verfasserin aut Felcia Lai verfasserin aut Roy R. Gerona verfasserin aut Mark Connor verfasserin aut David E. Hibbs verfasserin aut Elizabeth A. Cairns verfasserin aut Elizabeth A. Cairns verfasserin aut Michelle Glass verfasserin aut Adam Ametovski verfasserin aut Adam Ametovski verfasserin aut Samuel D. Banister verfasserin aut Samuel D. Banister verfasserin aut In Frontiers in Psychiatry Frontiers Media S.A., 2010 13(2022) (DE-627)631498796 (DE-600)2564218-2 16640640 nnns volume:13 year:2022 https://doi.org/10.3389/fpsyt.2022.1010501 kostenfrei https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 kostenfrei https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full kostenfrei https://doaj.org/toc/1664-0640 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 13 2022
allfieldsSound	10.3389/fpsyt.2022.1010501 doi (DE-627)DOAJ022902724 (DE-599)DOAJ8bb387539a3c4fa38d68649acedf0eb4 DE-627 ger DE-627 rakwb eng RC435-571 Eric Sparkes verfasserin aut Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity. synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry Eric Sparkes verfasserin aut Rochelle Boyd verfasserin aut Rochelle Boyd verfasserin aut Shuli Chen verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jack W. Markham verfasserin aut Jia Lin Luo verfasserin aut Jia Lin Luo verfasserin aut Tahira Foyzun verfasserin aut Humayra Zaman verfasserin aut Charlotte Fletcher verfasserin aut Charlotte Fletcher verfasserin aut Ross Ellison verfasserin aut Iain S. McGregor verfasserin aut Iain S. McGregor verfasserin aut Marina J. Santiago verfasserin aut Felcia Lai verfasserin aut Roy R. Gerona verfasserin aut Mark Connor verfasserin aut David E. Hibbs verfasserin aut Elizabeth A. Cairns verfasserin aut Elizabeth A. Cairns verfasserin aut Michelle Glass verfasserin aut Adam Ametovski verfasserin aut Adam Ametovski verfasserin aut Samuel D. Banister verfasserin aut Samuel D. Banister verfasserin aut In Frontiers in Psychiatry Frontiers Media S.A., 2010 13(2022) (DE-627)631498796 (DE-600)2564218-2 16640640 nnns volume:13 year:2022 https://doi.org/10.3389/fpsyt.2022.1010501 kostenfrei https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 kostenfrei https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full kostenfrei https://doaj.org/toc/1664-0640 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 13 2022
language	English
source	In Frontiers in Psychiatry 13(2022) volume:13 year:2022
sourceStr	In Frontiers in Psychiatry 13(2022) volume:13 year:2022
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking Psychiatry
isfreeaccess_bool	true
container_title	Frontiers in Psychiatry
authorswithroles_txt_mv	Eric Sparkes @@aut@@ Rochelle Boyd @@aut@@ Shuli Chen @@aut@@ Jack W. Markham @@aut@@ Jia Lin Luo @@aut@@ Tahira Foyzun @@aut@@ Humayra Zaman @@aut@@ Charlotte Fletcher @@aut@@ Ross Ellison @@aut@@ Iain S. McGregor @@aut@@ Marina J. Santiago @@aut@@ Felcia Lai @@aut@@ Roy R. Gerona @@aut@@ Mark Connor @@aut@@ David E. Hibbs @@aut@@ Elizabeth A. Cairns @@aut@@ Michelle Glass @@aut@@ Adam Ametovski @@aut@@ Samuel D. Banister @@aut@@
publishDateDaySort_date	2022-01-01T00:00:00Z
hierarchy_top_id	631498796
id	DOAJ022902724
language_de	englisch
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callnumber-first	R - Medicine
author	Eric Sparkes
spellingShingle	Eric Sparkes misc RC435-571 misc synthetic cannabinoid misc cannabinoid receptor 1 agonists misc pharmacology misc cannabinoids misc SCRAs misc docking misc Psychiatry Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
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topic_title	RC435-571 Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs synthetic cannabinoid cannabinoid receptor 1 agonists pharmacology cannabinoids SCRAs docking
topic	misc RC435-571 misc synthetic cannabinoid misc cannabinoid receptor 1 agonists misc pharmacology misc cannabinoids misc SCRAs misc docking misc Psychiatry
topic_unstemmed	misc RC435-571 misc synthetic cannabinoid misc cannabinoid receptor 1 agonists misc pharmacology misc cannabinoids misc SCRAs misc docking misc Psychiatry
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title	Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
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title_full	Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
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author_browse	Eric Sparkes Rochelle Boyd Shuli Chen Jack W. Markham Jia Lin Luo Tahira Foyzun Humayra Zaman Charlotte Fletcher Ross Ellison Iain S. McGregor Marina J. Santiago Felcia Lai Roy R. Gerona Mark Connor David E. Hibbs Elizabeth A. Cairns Michelle Glass Adam Ametovski Samuel D. Banister
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title_sort	synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists ab-4cn-butica, mmb-4cn-butinaca, mdmb-4f-butica, mdmb-4f-butinaca and their analogs
callnumber	RC435-571
title_auth	Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
abstract	Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity.
abstractGer	Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity.
abstract_unstemmed	Synthetic cannabinoid receptor agonists (SCRAs) continue to make up a significant portion new psychoactive substances (NPS) detected and seized worldwide. Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = < 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = < 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity.
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title_short	Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs
url	https://doi.org/10.3389/fpsyt.2022.1010501 https://doaj.org/article/8bb387539a3c4fa38d68649acedf0eb4 https://www.frontiersin.org/articles/10.3389/fpsyt.2022.1010501/full https://doaj.org/toc/1664-0640
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Due to their often potent activation of central cannabinoid receptors in vivo, use of SCRAs can result in severe intoxication, in addition to other adverse health effects. Recent detections of AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA and MDMB-4F-BUTINACA mark a continuation in the appearance of SCRAs bearing novel tail substituents. The proactive characterization campaign described here has facilitated the detection of several new SCRAs in toxicological case work. Here we detail the synthesis, characterization, and pharmacological evaluation of recently detected SCRAs, as well as a systematic library of 32 compounds bearing head, tail, and core group combinations likely to appear in future. In vitro radioligand binding assays revealed most compounds showed moderate to high affinity at both CB1 (pKi = &lt; 5 to 8.89 ± 0.09 M) and CB2 (pKi = 5.49 ± 0.03 to 9.92 ± 0.09 M) receptors. In vitro functional evaluation using a fluorescence-based membrane potential assay showed that most compounds were sub-micromolar to sub-nanomolar agonists at CB1 (pEC50 = &lt; 5 to 9.48 ± 0.14 M) and CB2 (pEC50 = 5.92 ± 0.16 to 8.64 ± 0.15 M) receptors. An in silico receptor-ligand docking approach was utilized to rationalize binding trends for CB2 with respect to the tail substituent, and indicated that rigidity in this region (i.e., 4-cyanobutyl) was detrimental to affinity.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">synthetic cannabinoid</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">cannabinoid receptor 1 agonists</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">pharmacology</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">cannabinoids</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">SCRAs</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">docking</subfield></datafield><datafield tag="653" ind1=" " ind2="0"><subfield code="a">Psychiatry</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Eric Sparkes</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Rochelle Boyd</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Rochelle Boyd</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Shuli Chen</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Jack W. 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Synthesis and pharmacological evaluation of newly detected synthetic cannabinoid receptor agonists AB-4CN-BUTICA, MMB-4CN-BUTINACA, MDMB-4F-BUTICA, MDMB-4F-BUTINACA and their analogs

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