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JWH-200

JWH-200
Clinical data
Other namesWIN 55,225
Legal status
Legal status
Identifiers
  • (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)
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C4=C3C=CC=C4)CCN5CCOCC5
  • 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]

  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 (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.
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