JWH-200

JWH-200
Clinical data
Other names	WIN 55,225
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (1-(2-Morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethanone;
CAS Number	103610-04-4 ;
PubChem CID	10045570;
ChemSpider	8221134;
UNII	9HN5J913P3;
CompTox Dashboard (EPA)	DTXSID60145946 ;
Chemical and physical data
Formula	C25H24N2O2
Molar mass	384.479 g·mol−1
3D model (JSmol)	Interactive image;
	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, K_i 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]

Legal status

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]

Germany

JWH-200 has been classified under the BtMG as Anlage II.^[9]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ ^a ^b "Poisons Standard". October 2015.
^ "Order Amending Schedule II to the Controlled Drugs and Substances Act (Synthetic Cannabinoids)". Government of Canada. 29 July 2015.
^ "Schedules of Controlled Substances: Temporary Placement of Four Synthetic Cannabinoids Into Schedule I". DEA Office of Diversion Control. Archived from the original on 28 February 2014. Retrieved 11 March 2014.
^ "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

[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.

[pmid15974991-2] 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.

[pmid1335057-5] 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.

[Poisons_Standard-6] "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. Archived from the original on 28 February 2014. Retrieved 11 March 2014.

[9] "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

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