JWH-368

Last updated • 1 min readFrom Wikipedia, The Free Encyclopedia
JWH-368
JWH-368.svg
Legal status
Legal status
Identifiers
  • [5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C26H24FNO
Molar mass 385.482 g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C=C1C2=CC(=CC=C2)F)C(=O)C3=CC=CC4=CC=CC=C43
  • InChI=1S/C26H24FNO/c1-2-3-6-15-28-18-21(17-25(28)20-11-7-12-22(27)16-20)26(29)24-14-8-10-19-9-4-5-13-23(19)24/h4-5,7-14,16-18H,2-3,6,15H2,1H3 Yes check.svgY
  • Key:OCOICOMCAJNSCA-UHFFFAOYSA-N Yes check.svgY

JWH-368 ([5-(3-Fluorophenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 16 ± 1nM) and CB2 (Ki = 9.1 ± 0.7nM) receptors, binding ~1.76 times stronger to the CB2 receptor than to the CB1 receptor. JWH-368 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor. [1]

Contents

Legality

In the United States JWH-368 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-368. [2] [3] [4] [5]

In Canada, JWH-368 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-368 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.

See also

Related Research Articles

JWH-073 Chemical compound

JWH-073, a synthetic cannabinoid, is an analgesic chemical from the naphthoylindole family that acts as a partial agonist at both the CB1 and CB2 cannabinoid receptors. It is somewhat selective for the CB1 subtype, with affinity at this subtype approximately 5x the affinity at CB2. The abbreviation JWH stands for John W. Huffman, one of the inventors of the compound.

JWH-147 Chemical compound

JWH-147 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 11.0 nM at CB1 vs 7.1 nM at CB2. It was discovered and named after John W. Huffman.

JWH-307 Chemical compound

JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2. It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.

JWH-210 Chemical compound

JWH-210 is an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both the CB1 and CB2 receptors, with Ki values of 0.46 nM at CB1 and 0.69 nM at CB2. It is one of the most potent 4-substituted naphthoyl derivatives in the naphthoylindole series, having a higher binding affinity (i.e. lower Ki) at CB1 than both its 4-methyl and 4-n-propyl homologues JWH-122 (CB1 Ki 0.69 nM) and JWH-182 (CB1 Ki 0.65 nM) respectively, and than the 4-methoxy compound JWH-081 (CB1 Ki 1.2 nM). It was discovered by and named after John W. Huffman.

JWH-120 Chemical compound

JWH-120 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-propyl analog of JWH-122. It is a potent and selective ligand for the CB2 receptor, but a weaker ligand for the CB1 receptor. It has a binding affinity of Ki = 6.1 ± 0.7 nM at the CB2 subtype and 173 times selectivity over the CB1 subtype.

JWH-149 Chemical compound

JWH-149 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-pentyl analog of JWH-148. It is a potent but only moderately selective ligand for the CB2 receptor, with a binding affinity of Ki = 0.73 ± 0.03 nM at this subtype, and more than six times selectivity over the CB1 subtype.

JWH-369

JWH-369 ((5-(2-chlorophenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent agonist of the CB1 (Ki = 7.9 ± 0.4nM) and CB2 (Ki = 5.2 ± 0.3nM) receptors, with a slight selectivity for the latter. JWH-369 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-373 Chemical compound

JWH-373 ([5-(2-butylphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 60 ± 3nM) and CB2 (Ki = 69 ± 2nM) receptors, with a slight selectivity for the former. JWH-373 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-309

JWH-309 (naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 41 ± 3nM) and CB2 (Ki = 49 ± 7nM) receptors, displaying a slight selectivity for the former. JWH-309 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-372

JWH-372 (naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent and selective agonist of the CB2 receptor. JWH-372 binds approximately 9 times stronger to the CB2 receptor (Ki = 8.2 ± 0.2nM) than the CB1 receptor (Ki = 77 ± 2nM). The selectivity of JWH-372 for the CB2 receptor is likely due to the electron-withdrawing character of the trifluoromethyl group rather than steric effects, as the o-methyl compound JWH-370 was only mildly selective for the CB2 receptor (CB1 Ki = 5.6 ± 0.4nM, CB2 Ki = 4.0 ± 0.5nM).

JWH-371

JWH-371 ([5-(4-butylphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 42 ± 1nM) and CB2 (Ki = 64 ± 2nM) receptors, binding ~1.5 times stronger to the CB1 receptor than the CB2 receptor. JWH-371 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-370

JWH-370 ([5-(2-methylphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 5.6 ± 0.4nM) and CB2 (Ki = 4.0 ± 0.5nM) receptors, with a slight selectivity for the CB2 receptor. JWH-370 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-367

JWH-367 ([5-(3-methoxyphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 53 ± 2nM) and CB2 (Ki = 23 ± 1nM) receptors, binding ~2.3 times stronger to the CB2 receptor than to the CB1 receptor. JWH-367 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-366

JWH-366 (naphthalen-1-yl-(1-pentyl-5-pyridin-3-ylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 191 ± 12nM) and CB2 (Ki = 24 ± 1nM) receptors, with a strong (~8x) selectivity for the CB2 receptor over the CB1 receptor. JWH-366 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-365

JWH-365 ((5-(2-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 17 ± 1nM) and CB2 (Ki = 3.4 ± 0.2nM) receptors, with a strong (~5x) selectivity for the CB2 receptor over the CB1 receptor. JWH-365 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-364

JWH-364 ([5-(4-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl](1-naphthyl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 34 ± 3nM) and CB2 (Ki = 29 ± 1nM) receptors, with a slight selectivity for the latter. JWH-364 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-363

JWH-363 (1-Naphthyl{1-pentyl-5-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 245 ± 5nM) and CB2 (Ki = 71 ± 1nM) receptors, with a moderate (~3.45x) selectivity for the latter. JWH-363 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-145 Chemical compound

JWH-145 (1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 14 ± 2nM) and CB2 (Ki = 6.4 ± 0.4nM) receptors, with a moderate (~2.2x) selectivity for the CB2 receptor. JWH-145 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-146 Chemical compound

JWH-146 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 21 ± 2nM) and CB2 (Ki = 62 ± 5nM) receptors, with a moderate (~2.9x) selectivity for the CB1 receptor over the CB2 receptor. JWH-146 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

JWH-150

JWH-150 ((1-butyl-5-phenylpyrrol-3-yl)-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 60 ± 1nM) and CB2 (Ki = 15 ± 2nM) receptors, with a moderate (4x) selectivity for the CB2 receptor. JWH-150 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

References

  1. Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID   16889960.
  2. 21 U.S.C.   § 812 : Schedules of controlled substances
  3. "The 2020 Florida Statutes". www.leg.state.fl.us. Retrieved 20 August 2021.
  4. "Arizona Revised Statutes Title 13. Criminal Code § 13-3401". www.azleg.gov. Retrieved 20 August 2021.
  5. "California Code, Health and Safety Code - HSC § 11357.5". Findlaw.