JWH-200

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JWH-200
JWH-200.svg
Systematic (IUPAC) name
(1-(2-morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethanone
Clinical data
Legal status
Identifiers
CAS Number 103610-04-4 YesY
PubChem CID 10045570
ChemSpider 8221134
Chemical data
Formula C25H24N2O2
Molar mass 384.469 g/mol
  (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.


Legal Status[edit]

Australia[edit]

JWH-200 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[5] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[5]

United States[edit]

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.[6] As of 16 July 2015, the drug is a controlled substance in Canada.[7]

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. 
  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. (1991). "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. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  6. ^ "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". DEA Office of Diversion Control. Retrieved 11 March 2014. 
  7. ^ http://www.gazette.gc.ca/rp-pr/p2/2015/2015-07-29/html/sor-dors192-eng.php