AM-1248

AM-1248

Systematic (IUPAC) name
1-[(N-methylpiperidin-2-yl)methyl]-3-(adamant-1-oyl)indole
Clinical data
Legal status	CA: Schedule II Temporary Class Drug (NZ)
Identifiers
CAS Number	335160-66-2 N
PubChem	CID 10293794
ChemSpider	8469262 N
Chemical data
Formula	C26H34N2O
Molar mass	390.561 g/mol
SMILES CN1CCCCC1Cn(c6)c2ccccc2c6C(=O)C5(C3)CC(CC3C4)CC4C5
InChI InChI=1S/C26H34N2O/c1-27-9-5-4-6-21(27)16-28-17-23(22-7-2-3-8-24(22)28)25(29)26-13-18-10-19(14-26)12-20(11-18)15-26/h2-3,7-8,17-21H,4-6,9-16H2,1H3 N Key:JRECAXBHMULNJQ-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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]

Legality

Sweden's public health agency suggested to classify AM-1248 as hazardous substance on June 1, 2015.^[5]

As of October 2015 AM-1248 is a controlled substance in China.^[6]

See also

• A-834,735
• AB-001
• AM-411
• AM-1220
• AM-2233
• Cannabipiperidiethanone

References

1. ↑ 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): 295–315. doi:10.1021/jm901214q. PMID 19921781. 
2. ↑ US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
3. ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
4. ↑ Jankovics P; et al. (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 214 (1-3): 27–32. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254. 
5. ↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Retrieved 29 June 2015. 
6. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.