Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox|
{{Drugbox
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|IUPAC_name = (6aR,10aR)-3-(1-hexylcyclopropyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
| verifiedrevid = 477236127
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| IUPAC_name = (6aR,10aR)-3-(1-hexylcyclopropyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
| image = AMG-41.svg
| image = AMG-41.svg
| width= 240
| width = 240

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| CAS_number=
<!--Clinical data-->
| ATC_prefix=
| tradename =
| ATC_suffix=
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| legal_status =
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| PubChem= 10361702
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| routes_of_administration =
| DrugBank=

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| C=25 | H=36 | O=2
<!--Pharmacokinetic data-->
| molecular_weight = 368.551 g/mol
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| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
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| CAS_number = 499237-35-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3062P60MH9
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| PubChem = 10361702
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8537151
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 19847

<!--Chemical data-->
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| C=25 | H=36 | O=2
| smiles = C=3CC2C(C)(C)Oc(cc(cc1O)C4(CC4)CCCCCC)c1C2CC=3C
| smiles = C=3CC2C(C)(C)Oc(cc(cc1O)C4(CC4)CCCCCC)c1C2CC=3C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| bioavailability=
| StdInChI = 1S/C25H36O2/c1-5-6-7-8-11-25(12-13-25)18-15-21(26)23-19-14-17(2)9-10-20(19)24(3,4)27-22(23)16-18/h9,15-16,19-20,26H,5-8,10-14H2,1-4H3/t19-,20-/m1/s1
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| metabolism =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| elimination_half-life=
| StdInChIKey = UVQIBKXDOZWHFU-WOJBJXKFSA-N
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| excretion =
| pregnancy_category =
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| legal_status =
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| routes_of_administration=
}}
}}


'''AMG-41''' is an [[analgesic]] drug which is a [[cannabinoid]] [[agonist]]. It is a derivative of Δ8[[THC]] substituted with a [[cyclopropane]] group on the 3-position side chain. AMG-41 is a potent agonist at both [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]], with a [[Dissociation constant|Ki]] of 0.4nM at CB<sub>1</sub> vs 0.9nM at CB<sub>2</sub>.<ref>Papahatjis DP, Nikas SP, Andreou T, Makriyannis A. Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols. ''Bioorganic and Medicinal Chemistry Letters''. 2002 Dec 16;12(24):3583-6. PMID 12443781</ref><ref>Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A. Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'. ''Journal of Medicinal Chemistry''. 2003 Jul 17;46(15):3221-9. PMID 12852753</ref><ref>Papahatjis DP, Nahmias VR, Nikas SP, Andreou T, Alapafuja SO, Tsotinis A, Guo J, Fan P, Makriyannis A. C1'-cycloalkyl side chain pharmacophore in tetrahydrocannabinols. ''Journal of Medicinal Chemistry''. 2007 Aug 23;50(17):4048-60. PMID 17672444</ref>
'''AMG-41''' (part of the [[List of AM cannabinoids|AM cannabinoid series]]) is an [[analgesic]] drug which is a [[cannabinoid]] [[agonist]]. It is a derivative of Δ<sup>8</sup>-[[THC]] substituted with a [[cyclopropyl group]] on the C1'-position of the C3-alkyl side chain. AMG-41 is a potent agonist at both [[Cannabinoid receptor 1|CB<sub>1</sub>]] and [[Cannabinoid receptor 2|CB<sub>2</sub>]], with a [[Dissociation constant|K<sub>i</sub>]] of 0.44&nbsp;nM at CB<sub>1</sub> vs 0.86&nbsp;nM at CB<sub>2</sub>.<ref>{{cite journal | vauthors = Papahatjis DP, Nikas SP, Andreou T, Makriyannis A | title = Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 24 | pages = 3583–6 | date = December 2002 | pmid = 12443781 | doi = 10.1016/s0960-894x(02)00785-0 }}</ref><ref>{{cite journal | vauthors = Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A | title = Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1' | journal = Journal of Medicinal Chemistry | volume = 46 | issue = 15 | pages = 3221–9 | date = July 2003 | pmid = 12852753 | doi = 10.1021/jm020558c }}</ref><ref>{{cite journal | vauthors = Papahatjis DP, Nahmias VR, Nikas SP, Andreou T, Alapafuja SO, Tsotinis A, Guo J, Fan P, Makriyannis A | display-authors = 6 | title = C1'-cycloalkyl side chain pharmacophore in tetrahydrocannabinols | journal = Journal of Medicinal Chemistry | volume = 50 | issue = 17 | pages = 4048–60 | date = August 2007 | pmid = 17672444 | doi = 10.1021/jm070121a }}</ref>


== See also ==
* [[AMG-3]]
* [[AMG-36]]


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== References ==
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{{cannabinoid-stub}}
{{reflist}}

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==References==
<references/>


{{cannabinoids}}
{{cannabinoids}}

[[Category:Cannabinoids]]
[[Category:Cannabinoids]]
[[Category:Benzochromenes]]
[[Category:Phenols]]


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{{cannabinoid-stub}}

Latest revision as of 21:46, 8 February 2024

AMG-41
Identifiers
  • (6aR,10aR)-3-(1-hexylcyclopropyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC25H36O2
Molar mass368.561 g·mol−1
3D model (JSmol)
  • C=3CC2C(C)(C)Oc(cc(cc1O)C4(CC4)CCCCCC)c1C2CC=3C
  • InChI=1S/C25H36O2/c1-5-6-7-8-11-25(12-13-25)18-15-21(26)23-19-14-17(2)9-10-20(19)24(3,4)27-22(23)16-18/h9,15-16,19-20,26H,5-8,10-14H2,1-4H3/t19-,20-/m1/s1 checkY
  • Key:UVQIBKXDOZWHFU-WOJBJXKFSA-N checkY
  (verify)

AMG-41 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with a cyclopropyl group on the C1'-position of the C3-alkyl side chain. AMG-41 is a potent agonist at both CB1 and CB2, with a Ki of 0.44 nM at CB1 vs 0.86 nM at CB2.[1][2][3]

See also[edit]

References[edit]

  1. ^ Papahatjis DP, Nikas SP, Andreou T, Makriyannis A (December 2002). "Novel 1',1'-chain substituted Delta(8)-tetrahydrocannabinols". Bioorganic & Medicinal Chemistry Letters. 12 (24): 3583–6. doi:10.1016/s0960-894x(02)00785-0. PMID 12443781.
  2. ^ Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A (July 2003). "Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'". Journal of Medicinal Chemistry. 46 (15): 3221–9. doi:10.1021/jm020558c. PMID 12852753.
  3. ^ Papahatjis DP, Nahmias VR, Nikas SP, Andreou T, Alapafuja SO, Tsotinis A, et al. (August 2007). "C1'-cycloalkyl side chain pharmacophore in tetrahydrocannabinols". Journal of Medicinal Chemistry. 50 (17): 4048–60. doi:10.1021/jm070121a. PMID 17672444.


source: https://en.wikipedia.org/w/index.php?title=AMG-41&diff=1205103350&oldid=345033344

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