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'''AM-905''' (part of the [[List of AM cannabinoids|AM cannabinoid series]]) is an [[analgesic]] drug which is a [[cannabinoid]] [[agonist]]. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]] receptors.<ref name="Busch-PetersenHill1996">{{cite journal|last1=Busch-Petersen|first1=Jakob|last2=Hill|first2=W. Adam|last3=Fan|first3=Pusheng|last4=Khanolkar|first4=Atmaram|last5=Xie|first5=Xuang-Qun|last6=Tius|first6=Marcus A.|last7=Makriyannis|first7=Alexandros|title=Unsaturated Side Chain β-11-Hydroxyhexahydrocannabinol Analogs|journal=Journal of Medicinal Chemistry|volume=39|issue=19|year=1996|pages=3790–3796|issn=0022-2623|doi=10.1021/jm950934b}}</ref> It is a potent and reasonably selective agonist for the [[Cannabinoid receptor 1|CB<sub>1</sub>]] cannabinoid [[Receptor (biochemistry)|receptor]], with a [[Dissociation constant|K<sub>i</sub>]] of 1.2nM at CB<sub>1</sub> and 5.3nM at [[Cannabinoid receptor 2|CB<sub>2</sub>]].<ref>Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A. Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. ''Journal of Medicinal Chemistry''. 1998 Mar 26;41(7):1195-200. PMID 9544219</ref> |
'''AM-905''' (part of the [[List of AM cannabinoids|AM cannabinoid series]]) is an [[analgesic]] drug which is a [[cannabinoid]] [[agonist]]. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]] receptors.<ref name="Busch-PetersenHill1996">{{cite journal|last1=Busch-Petersen|first1=Jakob|last2=Hill|first2=W. Adam|last3=Fan|first3=Pusheng|last4=Khanolkar|first4=Atmaram|last5=Xie|first5=Xuang-Qun|last6=Tius|first6=Marcus A.|last7=Makriyannis|first7=Alexandros|title=Unsaturated Side Chain β-11-Hydroxyhexahydrocannabinol Analogs|journal=Journal of Medicinal Chemistry|volume=39|issue=19|year=1996|pages=3790–3796|issn=0022-2623|doi=10.1021/jm950934b}}</ref> It is a potent and reasonably selective agonist for the [[Cannabinoid receptor 1|CB<sub>1</sub>]] cannabinoid [[Receptor (biochemistry)|receptor]], with a [[Dissociation constant|K<sub>i</sub>]] of 1.2nM at CB<sub>1</sub> and 5.3nM at [[Cannabinoid receptor 2|CB<sub>2</sub>]].<ref>Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A. Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. ''Journal of Medicinal Chemistry''. 1998 Mar 26;41(7):1195-200. PMID 9544219</ref> |
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==See |
==See also== |
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* [[AM-906]] - The corresponding ''Z'' or [[trans isomer]] |
* [[AM-906]] - The corresponding ''Z'' or [[trans isomer]] |
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* [[HU-243]] - Double bond replaced by [[geminal]] methyls for [[Thorpe–Ingold effect]] |
* [[HU-243]] - Double bond replaced by [[geminal]] methyls for [[Thorpe–Ingold effect]] |
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[[Category:Phenols]] |
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[[Category:AM cannabinoids]] |
[[Category:AM cannabinoids]] |
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{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
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Revision as of 00:40, 30 July 2016
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| Formula | C23H34O3 |
| Molar mass | 358.513 g/mol g·mol−1 |
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AM-905 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB1 and CB2 receptors.[1] It is a potent and reasonably selective agonist for the CB1 cannabinoid receptor, with a Ki of 1.2nM at CB1 and 5.3nM at CB2.[2]
See also
- AM-906 - The corresponding Z or trans isomer
- HU-243 - Double bond replaced by geminal methyls for Thorpe–Ingold effect
References
- ^ Busch-Petersen, Jakob; Hill, W. Adam; Fan, Pusheng; Khanolkar, Atmaram; Xie, Xuang-Qun; Tius, Marcus A.; Makriyannis, Alexandros (1996). "Unsaturated Side Chain β-11-Hydroxyhexahydrocannabinol Analogs". Journal of Medicinal Chemistry. 39 (19): 3790–3796. doi:10.1021/jm950934b. ISSN 0022-2623.
- ^ Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A. Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. Journal of Medicinal Chemistry. 1998 Mar 26;41(7):1195-200. PMID 9544219