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JWH-018

JWH-018
Clinical data
Routes of
administration
Drug classCannabinoid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life
Identifiers
  • (Naphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.163.574 Edit this at Wikidata
Chemical and physical data
FormulaC24H23NO
Molar mass341.454 g·mol−1
3D model (JSmol)
Solubility in waterhydrophobic, n/a mg/mL (20 °C)
  • CCCCCN1C=C(C(C2=CC=CC3=CC=CC=C32)=O)C4=CC=CC=C41
  • InChI=1S/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3 checkY
  • Key:JDNLPKCAXICMBW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO[3] or AM-678)[4] is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in animals similar to those of tetrahydrocannabinol (THC), a cannabinoid naturally present in cannabis, leading to its use as synthetic cannabinoid products that, in some countries, are sold legally as "incense blends".[5][6][7][8][9]

As a full agonist at both the CB1 and CB2 cannabinoid receptors, this chemical compound is classified as an analgesic medication.[10] The analgesic effects of cannabinoid ligands, mediated by CB1 receptors are well established in treatment of neuropathic pain, as well as cancer pain and arthritis.[10]

These compounds work by mimicking the body's naturally-produced endocannabinoid hormones such as 2-AG and anandamide (AEA), which are biologically active and can exacerbate or inhibit nerve signaling.[10] As the cause is poorly understood in chronic pain states, more research and development must be done before the therapeutic potential of this class of biologic compounds can be realized.[10]

  1. ^ "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Brazilian Health Regulatory Agency (published 25 July 2023). 24 July 2023. Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  2. ^ "Substance Details JWH-018". Retrieved 22 January 2024.
  3. ^ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
  4. ^ "Department of Justice :: Drug Enforcement Administration". 1 March 2011. Retrieved 2 March 2011.
  5. ^ Zimmermann US, Winkelmann PR, Pilhatsch M, Nees JA, Spanagel R, Schulz K (2009). "Withdrawal Phenomena and Dependence Syndrome After the Consumption of "Spice Gold"". Dtsch Ärztebl Int. 106 (27): 464–467. doi:10.3238/arztebl.2009.0464. PMC 2719097. PMID 19652769.
  6. ^ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding" (PDF). Drug and Alcohol Dependence. 60 (2): 133–140. doi:10.1016/S0376-8716(99)00152-0. PMID 10940540. Archived from the original (PDF) on 6 March 2016.
  7. ^ US patent 6900236, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2005-05-31 
  8. ^ US patent 7241799, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2007-07-10 
  9. ^ Atwood BK, Huffman J, Straiker A, Mackie K (June 2010). "JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB receptor agonist". British Journal of Pharmacology. 160 (3): 585–593. doi:10.1111/j.1476-5381.2009.00582.x. PMC 2931559. PMID 20100276.
  10. ^ a b c d Rani Sagar D, Burston JJ, Woodhams SG, Chapman V (December 2012). "Dynamic changes to the endocannabinoid system in models of chronic pain". Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences. 367 (1607): 3300–11. doi:10.1098/rstb.2011.0390. PMC 3481532. PMID 23108548.
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