AM-630: Difference between revisions

AM-630
Identifiers
	IUPAC name 1-[2-(morpholin-4-yl)ethyl]-2-methyl-3-(4-methoxybenzoyl)-6-iodoindole;
CAS Number	164178-33-0 ;
PubChem CID	4302963;
ChemSpider	3508738 ;
ChEMBL	ChEMBL181633 ;
CompTox Dashboard (EPA)	DTXSID10167719 ;
ECHA InfoCard	100.229.964
Chemical and physical data
Formula	C23H25IN2O3
Molar mass	504.360 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C4COCCN4CCn(c1C)c2cc(I)ccc2c1C(=O)c3ccc(OC)cc3;
	InChI InChI=1S/C23H25IN2O3/c1-16-22(23(27)17-3-6-19(28-2)7-4-17)20-8-5-18(24)15-21(20)26(16)10-9-25-11-13-29-14-12-25/h3-8,15H,9-14H2,1-2H3 ; Key:JHOTYHDSLIUKCJ-UHFFFAOYSA-N ;
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Revision as of 09:54, 6 June 2012

AM-630 (6-Iodopravadoline) is a drug that acts as a potent and selective inverse agonist for the cannabinoid receptor CB₂, with a K_i of 32.1nM at CB₂ and 165x selectivity over CB₁, at which it acted as a weak partial agonist.^[1] It is used in the study of CB₂ mediated responses and has been used to investigate the possible role of CB₂ receptors in the brain.^[2]^[3] AM-630 is significant as one of the first indole derived cannabinoid ligands substituted on the 6-position of the indole ring, a position that has subsequently been found to be important in determining affinity and efficacy at both the CB₁ and CB₂ receptors, and has led to the development of a large number of related derivatives that help users get their freak on.^[4]^[5]^[6]^[7]^[8]

References

^ Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology. 126 (3): 665–72. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Morgan NH, Stanford IM, Woodhall GL (2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology. 57 (4): 356–68. doi:10.1016/j.neuropharm.2009.07.017. PMID 19616018. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T (2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry. 67 (10): 974–82. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm00016a013, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm00016a013 instead.
^ Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
^ Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW (2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–402. doi:10.1016/S0960-894X(02)00466-3. PMID 12161142. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm7011613, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm7011613 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1039/c0md00022a, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1039/c0md00022a instead.

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

[pmid10188977-1] Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology. 126 (3): 665–72. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[pmid19616018-2] Morgan NH, Stanford IM, Woodhall GL (2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology. 57 (4): 356–68. doi:10.1016/j.neuropharm.2009.07.017. PMID 19616018. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[pmid19931854-3] Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T (2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry. 67 (10): 974–82. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[4] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm00016a013, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm00016a013 instead.

[5] Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.

[pmid12161142-6] Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW (2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–402. doi:10.1016/S0960-894X(02)00466-3. PMID 12161142. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[7] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm7011613, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm7011613 instead.

[8] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1039/c0md00022a, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1039/c0md00022a instead.

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-'''AM-630''' ('''6-Iodopravadoline''') is a drug that acts as a potent and selective [[inverse agonist]] for the [[cannabinoid receptor]] [[Cannabinoid receptor 2|CB<sub>2</sub>]], with a [[Dissociation constant#Protein-ligand binding|K<sub>i</sub>]] of 32.1nM at CB<sub>2</sub> and 165x selectivity over [[Cannabinoid receptor 1|CB<sub>1</sub>]], at which it acted as a weak [[partial agonist]].<ref name="pmid10188977">{{cite journal |author=Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG |title=Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630 |journal=British Journal of Pharmacology |volume=126 |issue=3 |pages=665–72 |year=1999 |month=February |pmid=10188977 |pmc=1565857 |doi=10.1038/sj.bjp.0702351 |url=}}</ref> It is used in the study of CB<sub>2</sub> mediated responses and has been used to investigate the possible role of CB<sub>2</sub> receptors in the brain.<ref name="pmid19616018">{{cite journal |author=Morgan NH, Stanford IM, Woodhall GL |title=Functional CB2 type cannabinoid receptors at CNS synapses |journal=Neuropharmacology |volume=57 |issue=4 |pages=356–68 |year=2009 |month=September |pmid=19616018 |doi=10.1016/j.neuropharm.2009.07.017 |url=}}</ref><ref name="pmid19931854">{{cite journal |author=Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T |title=Brain cannabinoid CB2 receptor in schizophrenia |journal=Biological Psychiatry |volume=67 |issue=10 |pages=974–82 |year=2010 |month=May |pmid=19931854 |doi=10.1016/j.biopsych.2009.09.024 |url=}}</ref> AM-630 is significant as one of the first indole derived cannabinoid ligands substituted on the 6-position of the indole ring, a position that has subsequently been found to be important in determining affinity and efficacy at both the CB<sub>1</sub> and CB<sub>2</sub> receptors, and has led to the development of a large number of related derivatives.<ref>{{Cite doi|10.1021/jm00016a013}}</ref><ref>[http://proquest.umi.com/pqdlink?did=726066941&Fmt=7&clientId=79356&RQT=309&VName=PQD Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.]</ref><ref name="pmid12161142">{{cite journal |author=Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW |title=C-3 Amido-indole cannabinoid receptor modulators |journal=Bioorganic & Medicinal Chemistry Letters |volume=12 |issue=17 |pages=2399–402 |year=2002 |month=September |pmid=12161142 |doi= 10.1016/S0960-894X(02)00466-3|url=}}</ref><ref>{{Cite doi|10.1021/jm7011613}}</ref><ref>{{Cite doi|10.1039/c0md00022a}}</ref>
+'''AM-630''' ('''6-Iodopravadoline''') is a drug that acts as a potent and selective [[inverse agonist]] for the [[cannabinoid receptor]] [[Cannabinoid receptor 2|CB<sub>2</sub>]], with a [[Dissociation constant#Protein-ligand binding|K<sub>i</sub>]] of 32.1nM at CB<sub>2</sub> and 165x selectivity over [[Cannabinoid receptor 1|CB<sub>1</sub>]], at which it acted as a weak [[partial agonist]].<ref name="pmid10188977">{{cite journal |author=Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG |title=Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630 |journal=British Journal of Pharmacology |volume=126 |issue=3 |pages=665–72 |year=1999 |month=February |pmid=10188977 |pmc=1565857 |doi=10.1038/sj.bjp.0702351 |url=}}</ref> It is used in the study of CB<sub>2</sub> mediated responses and has been used to investigate the possible role of CB<sub>2</sub> receptors in the brain.<ref name="pmid19616018">{{cite journal |author=Morgan NH, Stanford IM, Woodhall GL |title=Functional CB2 type cannabinoid receptors at CNS synapses |journal=Neuropharmacology |volume=57 |issue=4 |pages=356–68 |year=2009 |month=September |pmid=19616018 |doi=10.1016/j.neuropharm.2009.07.017 |url=}}</ref><ref name="pmid19931854">{{cite journal |author=Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T |title=Brain cannabinoid CB2 receptor in schizophrenia |journal=Biological Psychiatry |volume=67 |issue=10 |pages=974–82 |year=2010 |month=May |pmid=19931854 |doi=10.1016/j.biopsych.2009.09.024 |url=}}</ref> AM-630 is significant as one of the first indole derived cannabinoid ligands substituted on the 6-position of the indole ring, a position that has subsequently been found to be important in determining affinity and efficacy at both the CB<sub>1</sub> and CB<sub>2</sub> receptors, and has led to the development of a large number of related derivatives that help users get their freak on.<ref>{{Cite doi|10.1021/jm00016a013}}</ref><ref>[http://proquest.umi.com/pqdlink?did=726066941&Fmt=7&clientId=79356&RQT=309&VName=PQD Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.]</ref><ref name="pmid12161142">{{cite journal |author=Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW |title=C-3 Amido-indole cannabinoid receptor modulators |journal=Bioorganic & Medicinal Chemistry Letters |volume=12 |issue=17 |pages=2399–402 |year=2002 |month=September |pmid=12161142 |doi= 10.1016/S0960-894X(02)00466-3|url=}}</ref><ref>{{Cite doi|10.1021/jm7011613}}</ref><ref>{{Cite doi|10.1039/c0md00022a}}</ref>
 ==See also==