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Revision as of 10:45, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Revision as of 10:56, 17 February 2012 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:Ch...Next edit →
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{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 462653342 | verifiedrevid = 462653342
| IUPAC_name = (6aR,10aR)-3-(2-methyl-6-bromohex-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzochromen-1-ol | IUPAC_name = (6aR,10aR)-3-(2-methyl-6-bromohex-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzochromen-1-ol
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| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = | CAS_number =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 199561 | ChEMBL = 199561
| PubChem = 10717065 | PubChem = 10717065

Revision as of 10:56, 17 February 2012

Pharmaceutical compound
AM-087
Identifiers
IUPAC name
  • (6aR,10aR)-3-(2-methyl-6-bromohex-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzochromen-1-ol
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H33BrO2
Molar mass421.410 g/mol g·mol
3D model (JSmol)
SMILES
  • CC3(C)C1CC=C(C)CC1c2c(O)cc(C(C)(C)CCCCBr)cc2O3
InChI
  • InChI=1S/C23H33BrO2/c1-15-8-9-18-17(12-15)21-19(25)13-16(14-20(21)26-23(18,4)5)22(2,3)10-6-7-11-24/h8,13-14,17-18,25H,6-7,9-12H2,1-5H3/t17-,18-/m1/s1
  • Key:RJPGJHLVEUSRRA-QZTJIDSGSA-N
  (what is this?)  (verify)

AM-087 is an analgesic drug that is a cannabinoid agonist. It is a derivative of Δ8THC substituted on the 3-position side chain. AM-087 is a potent CB1 agonist with a Ki of 0.43nM, making it around 100x more potent than THC itself. This is most likely due to the bulky bromine substituent on the side chain.

See also

References

  1. Charalambous A, Lin S, Marciniak G, Banijamali A, Friend FL, Compton DR, Martin BR, Makriyannis A. Pharmacological evaluation of halogenated delta 8-THC analogs. Pharmacology, Biochemistry and Behaviour. 1991 Nov;40(3):509-12. PMID 1666915
  2. Nikas SP, Grzybowska J, Papahatjis DP, Charalambous A, Banijamali AR, Chari R, Fan P, Kourouli T, Lin S, Nitowski AJ, Marciniak G, Guo Y, Li X, Wang CL, Makriyannis A. The role of halogen substitution in classical cannabinoids: a CB1 pharmacophore model. AAPS Journal. 2004 Oct 19;6(4):e30. PMID 15760095
  3. Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X
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