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JWH-398

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-398
Legal status
Legal status
Identifiers
  • 1-Pentyl-3-(4-chloro-1-naphthoyl)indole
CAS Number
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H22ClNO
Molar mass375.90 g·mol−1
3D model (JSmol)
  • c14ccccc1n(CCCCC)cc4C(=O)c(cc3)c2ccccc2c3Cl
  • InChI=1S/C24H22ClNO/c1-2-3-8-15-26-16-21(19-11-6-7-12-23(19)26)24(27)20-13-14-22(25)18-10-5-4-9-17(18)20/h4-7,9-14,16H,2-3,8,15H2,1H3 ☒N
  • Key:IUWBHGFOHXVVKV-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-398 is ananalgesic chemical from thenaphthoylindole family, which acts as acannabinoid agonist at both the CB1 and CB2 receptors. It has mild selectivity for CB1 with a Ki of 2.3 nM and 2.8 nM at CB2.[2] This synthetic chemical compound was identified by theEMCDDA as an ingredient in three separate "herbal incense" products purchased from online shops between February and June 2009.[3] It was discovered by, and named after,John W. Huffman.[4]

In the United States, JWH-398 is aSchedule I controlled substance.[5]

See also

[edit]

References

[edit]
  1. ^Grozījumi Ministru kabineta 2005.gada 8.novembra noteikumos Nr.847 "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem"
  2. ^Huffman JW (2009). Reggio PH (ed.).Cannabimimetic Indoles, Pyrroles, and Indenes: Structure–Activity Relationships and Receptor Interactions. The Cannabinoid Receptors. The Receptors. Humana Press.doi:10.1007/978-1-59745-503-9.ISBN 978-1-58829-712-9.
  3. ^"Understanding the 'Spice' phenomenon"(PDF). Lisbon: EMCDDA. November 2009. Archived fromthe original(PDF) on 2010-04-08. Retrieved2009-11-05.
  4. ^Huffman JW, et al. (2009).Structure-Activity Relationships at the cb1 and cb2 Receptors for 1-Alkyl-3-(1-Naphthoyl-4 and 8-Halogen Substituted) Indoles. 19th Annual Symposium on the Cannabinoids. Burlington, Vermont: International Cannabinoid Research Society. p. 2.
  5. ^Controlled Substances listed by the DEA
Phytocannabinoids
(comparison)
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agonists /
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Naphthoylindazoles
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Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
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propanoylindoles
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AllostericCBRTooltip Cannabinoid receptorligands
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(inactivation inhibitors)
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