JWH-200

From Wikipedia, the free encyclopedia
Jump to: navigation, search
JWH-200
JWH-200.svg
Systematic (IUPAC) name
(1-(2-morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethanone
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Identifiers
CAS number 103610-04-4 YesY
ATC code ?
PubChem CID 10045570
ChemSpider 8221134
Chemical data
Formula C25H24N2O2 
Mol. mass 384.469 g/mol
 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.

The US DEA temporarily declared JWH-200 a schedule I controlled substance on 1 March 2011 through 76 FR 11075, and permanently instated the same schedule on 9 July 2012 in the Section 1152 of the Food and Drug Administration Safety and Innovation Act.[5] As of 26 June 2011, the drug is legal in Canada.[6]

See also[edit]

References[edit]

  1. ^ Dutta, A. K. , E. A. ; 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, et al.. "Antinociceptive (aminoalkyl)indoles". Journal of Medicinal Chemistry 34 (3): 1099–1110. doi:10.1021/jm00107a034. PMID 1900533. 
  4. ^ Compton, DR, et al. (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. ^ "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". DEA Office of Diversion Control. Retrieved 11 March 2014. 
  6. ^ http://laws.justice.gc.ca/en/C-38.8/