JWH-018

JWH-018
Clinical data
Trade names	Spice, K2
Routes of; administration	Smoked, Oral
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule II, In general uncontrolled could be illegal to sell for human consumption or the analogue acts in several countries.; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; UN: Psychotropic Schedule II;
Identifiers
	IUPAC name (Naphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone;
CAS Number	209414-07-3 ;
PubChem CID	10382701;
ChemSpider	8558143 ;
UNII	G391998J57;
KEGG	C22748 ;
ChEMBL	ChEMBL561013 ;
CompTox Dashboard (EPA)	DTXSID10175117 ;
ECHA InfoCard	100.163.574
Chemical and physical data
Formula	C24H23NO
Molar mass	341.454 g·mol−1
3D model (JSmol)	Interactive image;
Solubility in water	hydrophobic, n/a mg/mL (20 °C)
	SMILES CCCCCN1C=C(C(C2=CC=CC3=CC=CC=C32)=O)C4=CC=CC=C41;
	InChI 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 ; Key:JDNLPKCAXICMBW-UHFFFAOYSA-N ;
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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 in synthetic cannabis 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]

^ "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.
^ "Substance Details JWH-018". Retrieved 22 January 2024.
^ 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.
^ "Department of Justice :: Drug Enforcement Administration". 1 March 2011. Retrieved 2 March 2011.
^ 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.
^ 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.
^ US patent 6900236, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2005-05-31
^ US patent 7241799, Alexandros Makriyannis, Hongfeng Deng, "Cannabimimetic indole derivatives", issued 2007-07-10
^ 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.
^ ^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.

[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.

[pmid36346325-3] 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.

[ReferenceA-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.

[Aung-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

[wiley1-9] 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.

[:0-10] 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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Clinical data


Trade names	Spice, K2
Routes of administration	Smoked, Oral
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] CA: Schedule II, In general uncontrolled could be illegal to sell for human consumption or the analogue acts in several countries. DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I UN: Psychotropic Schedule II^[2]
Identifiers
IUPAC name (Naphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone
CAS Number	209414-07-3^N
PubChem CID	10382701
ChemSpider	8558143^Y
UNII	G391998J57
KEGG	C22748^Y
ChEMBL	ChEMBL561013^Y
CompTox Dashboard (EPA)	DTXSID10175117
ECHA InfoCard	100.163.574
Chemical and physical data
Formula	C₂₄H₂₃NO
Molar mass	341.454 g·mol⁻¹
3D model (JSmol)	Interactive image
Solubility in water	hydrophobic, n/a mg/mL (20 °C)
SMILES CCCCCN1C=C(C(C2=CC=CC3=CC=CC=C32)=O)C4=CC=CC=C41
InChI 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^Y Key:JDNLPKCAXICMBW-UHFFFAOYSA-N^Y
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