JWH-200

JWH-200
Clinical data
Other namesWIN 55,225
Legal status
Legal status
Identifiers
IUPAC name
  • (1-(2-Morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H24N2O2
Molar mass384.479 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C4=C3C=CC=C4)CCN5CCOCC5
InChI
  • InChI=1S/C25H24N2O2/c28-25(22-10-5-7-19-6-1-2-8-20(19)22)23-18-27(24-11-4-3-9-21(23)24)13-12-26-14-16-29-17-15-26/h1-11,18H,12-17H2
  • Key:SZWYXJHTNGJPKU-UHFFFAOYSA-N
  (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, Ki at the CB1 receptor is 42 nM, 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 in 1991 by Sterling Drug as a potential analgesic following the earlier identification of related compounds such as pravadoline and WIN 55,212-2.[5]

Australia

JWH-200 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[6] 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.[6]

Canada

In July 2015, JWH-200 became a controlled substance in Canada.[7]

United States

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.[8]

See also

References

  1. ↑ Dutta AK, Ryan W, Thomas BF, Singer M, Compton DR, Martin BR, Razdan RK (August 1997). "Synthesis, pharmacology, and molecular modeling of novel 4-alkyloxy indole derivatives related to cannabimimetic aminoalkyl indoles (AAIs)". Bioorganic & Medicinal Chemistry. 5 (8): 1591–600. doi:10.1016/S0968-0896(97)00111-9. PMID 9313864.
  2. ↑ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
  3. ↑ Bell MR, D'Ambra TE, Kumar V, Eissenstat MA, Herrmann JL, Wetzel JR, et al. (March 1991). "Antinociceptive (aminoalkyl)indoles". Journal of Medicinal Chemistry. 34 (3): 1099–110. doi:10.1021/jm00107a034. PMID 1900533.
  4. ↑ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (December 1992). "Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol". The Journal of Pharmacology and Experimental Therapeutics. 263 (3): 1118–26. PMID 1335057.
  5. ↑ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR. Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. J Pharmacol Exp Ther. 1992 Dec;263(3):1118-26. {{pmid| 1335057}
  6. 1 2 "Poisons Standard". October 2015.
  7. ↑ "Order Amending Schedule II to the Controlled Drugs and Substances Act (Synthetic Cannabinoids)". Government of Canada. 29 July 2015.
  8. ↑ "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". DEA Office of Diversion Control. Retrieved 11 March 2014.
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