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]

^ 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.

[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.

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