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JWH-167
Names
Preferred IUPAC name
1-(1-Pentyl-1H -indol-3-yl)-2-phenylethan-1-one
Identifiers
ChEMBL
ChemSpider
UNII
InChI=1S/C21H23NO/c1-2-3-9-14-22-16-19(18-12-7-8-13-20(18)22)21(23)15-17-10-5-4-6-11-17/h4-8,10-13,16H,2-3,9,14-15H2,1H3
Y Key: AMCPOEOUXQWESI-UHFFFAOYSA-N
Y
CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3
Properties
C 21 H 23 N O
Molar mass
305.421 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
JWH-167 (1-pentyl-3-(phenylacetyl)indole ) is a
synthetic cannabinoid from the
phenylacetylindole family, which acts as a
cannabinoid agonist with about 1.75 times selectivity for
CB1 with a
Ki of 90 nM ± 17 and 159 nM ± 14 at
CB2 . Similar to the related 2'-
methoxy compound
JWH-250 , and the 2'-
chloro compound
JWH-203 , JWH-167 has a
phenyl
acetyl group in place of the
naphthoyl ring used in most
aminoalkylindole
cannabinoid compounds.
[1]
[2]
In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-167 are
Schedule I Controlled Substances .
[3]
References
^ 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 .
^ 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 .
^
21 U.S.C.
§ 812 : Schedules of controlled substances
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
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)