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JWH-200

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JWH-200
Systematic (IUPAC) name
(1-(2-morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethanone
Clinical data
Pregnancy cat.  ?
Legal status Schedule I (US)
Identifiers
CAS number 103610-04-4 YesY
ATC code  ?
PubChem CID 10045570
Chemical data
Formula C25H24N2O2 
Mol. mass 384.469 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

JWH-200 (WIN 55,225)[1] is an analgesic chemical from the aminoalkylindole family that acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 42nM, around the same as that of THC,[2] but its analgesic potency in vivo was higher than that of other analogues with stronger CB1 binding affinity in vitro,[3] around 3 times that of THC but with less sedative effect,[4] most likely reflecting favourable pharmacokinetic characteristics. It was discovered by, and named after, Dr. John W. Huffman. On March 1, 2011, the United States DEA temporarily placed JWH-200 under Schedule I of the Controlled Substances Act (along with four other synthetic cannabinoids),[5]where it will remain for 12 months while it is researched and considered for permanent scheduling. In Canada, the drug is legal and not controlled (as of June 26, 2011).[6]

[edit] See also

[edit] References

  1. ^ Dutta, A. K.; Ryan, W.; Thomas, B. F.; Singer, M.; Compton, D. R.; Martin, B. R.; Razdan, R. K. (1997). "Synthesis, pharmacology, and molecular modeling of novel 4-alkyloxy indole derivatives related to cannabimimetic aminoalkyl indoles (AAIs)". Bioorganic & medicinal chemistry 5 (8): 1591–1600. doi:10.1016/S0968-0896(97)00111-9. PMID 9313864.  edit
  2. ^ Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. Current Medicinal Chemistry, 2005; 12: 1395-1411.
  3. ^ Bell, MR; D'Ambra, TE; Kumar, V; Eissenstat, MA; Herrmann Jr, JL; Wetzel, JR; Rosi, D; Philion, RE et al (1991). "Antinociceptive (aminoalkyl)indoles". Journal of Medicinal Chemistry 34 (3): 1099–1110. doi:10.1021/jm00107a034. PMID 1900533. 
  4. ^ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". Journal of Pharmacology and Experimental Therapeutics 263 (3): 1118–26. PMID 1335057. 
  5. ^ http://www.federalregister.gov/articles/2011/03/01/2011-4428/schedules-of-controlled-substances-temporary-placement-of-five-synthetic-cannabinoids-into-schedule
  6. ^ http://laws.justice.gc.ca/en/C-38.8/
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