SDB-001

This article is about the cannabinoid drug. For the South Korean girl band, see 2NE1. For the metabotropic glutamate receptor antagonist, see APICA (drug).
SDB-001
Systematic (IUPAC) name
1-pentyl-N-tricyclo[3.3.1.13,7]dec-1-yl-1H-indole-3-carboxamide
Clinical data
  • US: covered under the Federal Analogue Act in the United States and under similar bills in other countries
  • Illegal in Japan
Identifiers
1345973-50-3 Yes
Chemical data
Formula C24H32N2O
364.522 g/mol

SDB-001 (2NE1, APICA, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide) is a drug that acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in March 2012 as an ingredient in synthetic cannabis smoking blends, along with a related compound APINACA (sold as "AKB48").[1] Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with an indole core instead of indazole, and a simple pentyl chain on the indole 1-position. Pharmacological testing determined SDB-001 to have an IC50 of 175nM at CB1, only slightly less potent than JWH-018 which had an IC50 of 169nM, but over four times more tightly binding than AKB48, which had an IC50 of 824nM.[2] The first published synthesis and pharmacological evaluation of SDB-001 revealed that it acts as a full agonist at CB1 (EC50 = 34 nM) and CB2 receptors (EC50 = 29 nM).[3] Furthermore, SDB-001 possesses cannabis-like effects in rats, and appears to be less potent than JWH-018 but more potent than THC.[3]

See also

References

  1. ↑ Uchiyama, N.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (2012). "Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products". Forensic Toxicology 30 (2): 114. doi:10.1007/s11419-012-0136-7.
  2. ↑ Uchiyama, N.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (2012). "URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products". Forensic Science International 227 (1–3): 21–32. doi:10.1016/j.forsciint.2012.08.047. PMID 23063179.
  3. ↑ 3.0 3.1 Banister, S. D.; Wilkinson, S. M.; Longworth, M.; Stuart, J.; Apetz, N.; English, K.; Brooker, L.; Goebel, C.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: Novel cannabimimetic drugs of abuse". ACS Chemical Neuroscience 4 (7): 130403084729007. doi:10.1021/cn400035r.