MN-25

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Chemical compound

title: "MN-25" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["aminoalkylindoles", "cannabinoids", "designer-drugs", "indoles", "indolecarboxamides"] description: "Chemical compound" topic_path: "general/aminoalkylindoles" source: "https://en.wikipedia.org/wiki/MN-25" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 459128585 | IUPAC_name = 7-methoxy-1-(2-morpholin-4-ylethyl)-N-[(1R,3S,4S)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide | image = MN-25 structure.svg | image_class = skin-invert-image | width =

| pregnancy_category = | legal_CA = Schedule II | legal_DE = NpSG | legal_UK = Class B | legal_status =

| CAS_number_Ref = | CAS_number = 501926-82-5 | CAS_number2 = 501927-29-3 | index_label = | index2_label = 2-methyl derivative | ATC_prefix = | ATC_suffix = | UNII = 8WXU5YRE25 | UNII_Ref = | PubChem = 71308243 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 26286811 | ChEMBL = 3234671 | synonyms = N-[(S)-Fenchyl]-1-[2-(morpholin-4-yl)ethyl]-7-methoxyindole-3-carboxamide | C=26|H=37|N=3|O=3 | smiles = COC1=C(N(CCN2CCOCC2)C=C3C(N[C@H]4[C@@]5(C)CCC@HC4(C)C)=O)C3=CC=C1 | StdInChI_Ref = | StdInChI = 1S/C26H37N3O3/c1-25(2)18-8-9-26(3,16-18)24(25)27-23(30)20-17-29(11-10-28-12-14-32-15-13-28)22-19(20)6-5-7-21(22)31-4/h5-7,17-18,24H,8-16H2,1-4H3,(H,27,30)/t18-,24-,26+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = VQGDMQICNRCQEH-UFKXBGGNSA-N

MN-25 (UR-12) is a drug invented by Bristol-Myers Squibb, that acts as a reasonably selective agonist of peripheral cannabinoid receptors. It has moderate affinity for CB2 receptors with a Ki of 11 nM, but 22x lower affinity for the psychoactive CB1 receptors with a Ki of 245 nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a Ki of 8 nM at CB1 and 29 nM at CB2, which contrasts with the usual trend of 2-methyl derivatives having increased selectivity for CB2 (cf. JWH-018 vs JWH-007, JWH-081 vs JWH-098).

Chemically, it is closely related to another indole-3-carboxamide synthetic cannabinoid, Org 28611, but with a different cycloalkyl substitution on the carboxamide, and the cyclohexylmethyl group replaced by morpholinylethyl, as in JWH-200 or A-796,260. Early compounds such as these have subsequently led to the development of many related indole-3-carboxamide cannabinoid ligands.

References

References

  1. "Cannabinoid Receptor Modulators, Their Processes of Preparation, and use of Cannabinoid Receptor Modulators for Treating Respiratory and Non-Respiratory Diseases".
  2. (20 December 2009). "Improved procedure for the preparation of 7-methoxy-2-methyl-1-(2-morpholinoethyl)-1H-indole-3-carboxylic acid, key intermediate in the synthesis of novel 3-amidoindole and indolopyridone cannabinoid ligands". Arkivoc.
  3. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters.
  4. (May 2003). "Rational design and synthesis of an orally active indolopyridone as a novel conformationally constrained cannabinoid ligand possessing antiinflammatory properties". Journal of Medicinal Chemistry.
  5. (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry.
  6. (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry.
  7. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists". [[Royal Society of Chemistry]].
  8. (August 2010). "Design, synthesis, and structure-activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists". Bioorganic & Medicinal Chemistry Letters.
  9. (December 2010). "Design, synthesis, and structure-activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists". Bioorganic & Medicinal Chemistry Letters.

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aminoalkylindolescannabinoidsdesigner-drugsindolesindolecarboxamides