AM-1248
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AM-1248
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| Systematic (IUPAC) name | |
| 1-[(N-methylpiperidin-2-yl)methyl]-3-(adamant-1-oyl)indole | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Temporary Class Drug (NZ) |
| Identifiers | |
| CAS number | 335160-66-2  |
| ATC code | ? |
| PubChem | CID 10293794 |
| Chemical data | |
| Formula | C26H34N2O |
| Mol. mass | 390.561 g/mol |
| SMILES | eMolecules & PubChem |
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AM-1248 is a drug that acts as a moderately potent agonist for both the cannabinoid receptors CB1 and CB2, but with some dispute between sources over its exact potency and selectivity. Replacing the 3-(1-naphthoyl) group found in many indole derived cannabinoid ligands, with an adamantoyl group, generally confers significant CB2 selectivity,[1] but reasonable CB1 affinity and selectivity is retained when an N-methylpiperidin-2-ylmethyl substitution is used at the indole 1-position.[2][3] The related compound 1-pentyl-3-(1-adamantoyl)indole was identified as having been sold as a cannabinoid designer drug in Hungary in 2011, along with another synthetic cannabinoid AM-679.[4]
See also
References
- ^ Frost, J. M.; Dart, M. J.; Tietje, K. R.; Garrison, T. R.; Grayson, G. K.; Daza, A. V.; El-Kouhen, O. F.; Yao, B. B. 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.
- ^ US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
- ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- ^ Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (August 2011). "Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary". Forensic Science International. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254.
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