Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 451606850
| verifiedrevid = 451606850
| IUPAC_name = (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone
| IUPAC_name = (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone
| image = JWH-198_structure.png
| image = JWH-198.svg
| width = 220
| width = 150


<!--Clinical data-->
<!--Clinical data-->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = Schedule II
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = Schedule I
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 166599-76-4
| CAS_number = 166599-76-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J53IGM38PB
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=26 | N=2 | O=3
| C=26 | H=26 | N=2 | O=3
| molecular_weight = 414.495 g/mol
| smiles = C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3
| smiles = C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3
| InChI = 1/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3
| InChIKey = QWHSUXWDDKWTOG-UHFFFAOYAM
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3
| StdInChI = 1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3
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}}
}}


'''JWH-198''' is a drug from the [[aminoalkylindole]] family which acts as a [[cannabinoid]] [[Receptor (biochemistry)|receptor]] [[agonist]]. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a [[Dissociation constant|binding affinity]] at the CB<sub>1</sub> receptor of 10nM, binding around four times more tightly than the parent compound [[JWH-200]], which has no substitution on the naphthoyl ring.<ref>Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. ''Current Medicinal Chemistry'', 2005; 12: 1395-1411.</ref> It has been used mainly in [[molecular modelling]] of the cannabinoid receptors.<ref name="pmid7636873">{{cite journal |vauthors=Eissenstat MA, etal |title=Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics |journal=Journal of Medicinal Chemistry |volume=38 |issue=16 |pages=3094–105 |date=August 1995 |pmid=7636873 |doi= 10.1021/jm00016a013 }}</ref><ref name="pmid9804691">{{cite journal |vauthors=Shim JY, etal |title=Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis |journal=Journal of Medicinal Chemistry |volume=41 |issue=23 |pages=4521–32 |date=November 1998 |pmid=9804691 |doi=10.1021/jm980305c }}</ref>
'''JWH-198''' is a drug from the [[aminoalkylindole]] and [[naphthoylindole]] families which acts as a [[cannabinoid receptor]] [[agonist]]. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a [[Dissociation constant|binding affinity]] at the CB<sub>1</sub> receptor of 10&nbsp;nM, binding around four times more tightly than the parent compound [[JWH-200]], which has no substitution on the naphthoyl ring.<ref name="pmid15974991">{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | year = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }}</ref> It has been used mainly in [[molecular modelling]] of the cannabinoid receptors.<ref name="pmid7636873">{{cite journal | vauthors = Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM | title = Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 16 | pages = 3094–105 | date = Aug 1995 | pmid = 7636873 | doi = 10.1021/jm00016a013 }}</ref><ref name="pmid9804691">{{cite journal | vauthors = Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ | title = Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 23 | pages = 4521–32 | date = Nov 1998 | pmid = 9804691 | doi = 10.1021/jm980305c }}</ref>


In the United States, all CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>
⚫
==See also==

⚫
== See also ==
* [[JWH-081]]
* [[JWH-081]]
* [[JWH-193]]
* [[JWH-193]]


==References==
== References ==
{{Reflist}}
{{Reflist}}


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[[Category:Aminoalkylindoles]]
[[Category:Aminoalkylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Morpholines]]
[[Category:4-Morpholinyl compounds]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:CB1 receptor agonists]]



{{cannabinoid-stub}}
{{cannabinoid-stub}}

Latest revision as of 13:18, 10 July 2023

JWH-198
Legal status
Legal status
Identifiers
  • (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26N2O3
Molar mass414.505 g·mol−1
3D model (JSmol)
  • C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3
  • InChI=1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3 ☒N
  • Key:QWHSUXWDDKWTOG-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-198 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a binding affinity at the CB1 receptor of 10 nM, binding around four times more tightly than the parent compound JWH-200, which has no substitution on the naphthoyl ring.[1] It has been used mainly in molecular modelling of the cannabinoid receptors.[2][3]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are Schedule I Controlled Substances.[4]

See also[edit]

References[edit]

  1. ^ 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.
  2. ^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM (Aug 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.
  3. ^ Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ (Nov 1998). "Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis". Journal of Medicinal Chemistry. 41 (23): 4521–32. doi:10.1021/jm980305c. PMID 9804691.
  4. ^ 21 U.S.C. § 812: Schedules of controlled substances
source: https://en.wikipedia.org/w/index.php?title=JWH-198&diff=1164683136&oldid=703451229

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