Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

JWH-203

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-203
Legal status
Legal status
Identifiers
  • 2-(2-Chlorophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.233.381Edit this at Wikidata
Chemical and physical data
FormulaC21H22ClNO
Molar mass339.86 g·mol−1
3D model (JSmol)
  • Clc2ccccc2CC(=O)c1cn(CCCCC)c3ccccc13
  • InChI=1S/C21H22ClNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3
  • Key:YDINKDBAZJOSLV-UHFFFAOYSA-N
  (verify)

JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is ananalgesic chemical from thephenylacetylindole family that acts as acannabinoidagonist with approximately equal affinity at both theCB1 andCB2 receptors, having aKi of 8.0 nM at CB1 and 7.0 nM at CB2. It was originally discovered by, and named after,John W. Huffman, but has subsequently been sold without his permission as an ingredient ofsynthetic cannabis smoking blends.[2] Similar to the related 2'-methoxy compoundJWH-250, the 2'-bromo compoundJWH-249, and the 2'-methyl compoundJWH-251, JWH-203 has aphenylacetyl group in place of thenaphthoyl ring used in mostaminoalkylindole cannabinoid compounds, and has the strongestin vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.[3][4][5]

Unexpectedly despite its weaker CB1 Kiin vitro, the2-methylindole derivative JWH-204 is actually more potent than JWH-203 in animal tests for cannabinoid activity, though it is still weaker thanJWH-249.[6]

JWH-204

Legal status

[edit]

In the United States, JWH-203 is aSchedule I Controlled Substance.[7]

As of October 2015, JWH-203 is a controlled substance in China.[8]

See also

[edit]

References

[edit]
  1. ^"Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved17 June 2011.
  2. ^Bononi M, Belgi P, Tateo F (July 2011)."Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203"(PDF).Journal of Analytical Toxicology.35 (6):360–3.doi:10.1093/anatox/35.6.360.PMID 21740693.
  3. ^Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles".Bioorganic & Medicinal Chemistry Letters.15 (18):4110–3.doi:10.1016/j.bmcl.2005.06.008.PMID 16005223.
  4. ^Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands".Mini Reviews in Medicinal Chemistry.8 (4):370–87.doi:10.2174/138955708783955935.PMID 18473928.
  5. ^Bononi M, Belgi P, Tateo F (July 2011)."Analytical data for identification of the Cannabimimetic Phenylacetylindole JWH-203"(PDF).Journal of Analytical Toxicology.35 (6):360–3.doi:10.1093/anatox/35.6.360.PMID 21740693.
  6. ^Wiley JL, Marusich JA, Martin BR, Huffman JW (June 2012)."1-Pentyl-3-phenylacetylindoles and JWH-018 share in vivo cannabinoid profiles in mice".Drug and Alcohol Dependence.123 (1–3):148–53.doi:10.1016/j.drugalcdep.2011.11.001.PMC 3294131.PMID 22127210.
  7. ^"Controlled Substances"(PDF).Drug Enforcement Administration.
  8. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)

Retrieved from "https://en.wikipedia.org/w/index.php?title=JWH-203&oldid=1268800185"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp