N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide
Systematic (IUPAC) name | |
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7-methoxy-1-(2-morpholinoethyl)-N-((1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)-1H-indole-3-carboxamide
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Identifiers | |
CAS Number | 501926-82-5 501927-29-3 (2-methyl derivative) |
PubChem | CID: 44307202 |
ChemSpider | 26286811 |
UNII | 8WXU5YRE25 |
Chemical data | |
Formula | C26H37N3O3 |
Molecular mass | 439.59 g/mol |
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7-methoxy-1-(2-morpholinoethyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)-1H-indole-3-carboxamide (N-[(S)-fenchyl]-1-[2-(morpholin-4-yl)ethyl]-7-methoxyindole-3-carboxamide, UR-12, MN-25) is a drug invented by Bristol-Myers Squibb,[1] that acts as a reasonably selective agonist of peripheral cannabinoid receptors.[2] It has moderate affinity for CB2 receptors with a Ki of 11nM, but 22x lower affinity for the psychoactive CB1 receptors with a Ki of 245nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a Ki of 8nM at CB1 and 29nM at CB2,[3][4] 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).[5][6]
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 a large number of related indole-3-carboxamide cannabinoid ligands.[7][8][9][10]
See also
References
- ↑ CANNABINOID RECEPTOR MODULATORS, THEIR PROCESSES OF PREPARATION, AND USE OF CANNABINOID RECEPTOR MODULATORS IN TREATING RESPIRATORY AND NON-RESPIRATORY DISEASES. WO 2001/58869
- ↑ Rulin Zhao, et al. 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 2010 (vi):89-95.
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Further reading
1. John Hynes., et al. C3 AMIDO-INDOLE CANNABINOID RECEPTOR MODULATORS. Bioorganic and Medical Chemistry Letters. Volume 12 issue 17, 2 September 2002 pages 2399-2402
2. Frost, J. M., et al. (2010). "Indol -3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry 53 (1): 295. doi :10.1021/ jm901214q. PMID 19921781
3. Chin CL, et al. (January 2008). "Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI". British Journal of Pharmacology 153 (2): 367–79. doi :10.1038/ sj.bjp .0707506. PMC 2219521. PMID 17965748
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- Aminoalkylindoles
- Cannabinoids
- Designer drugs
- Indoles
- Indolecarboxamides