Content deleted Content added
m <ref> clean up |
JJMC89 bot III (talk | contribs) m Moving Category:4-Morpholinyl compunds to Category:4-Morpholinyl compounds per Wikipedia:Categories for discussion/Speedy |
||
(15 intermediate revisions by 12 users not shown) | |||
Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{Drugbox |
{{Drugbox |
||
| Verifiedfields = changed |
| Verifiedfields = changed |
||
| verifiedrevid = 451606850 |
| verifiedrevid = 451606850 |
||
| IUPAC_name = (1-(2- |
| IUPAC_name = (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone |
||
| image = JWH- |
| image = JWH-198.svg |
||
| width = |
| width = 150 |
||
<!--Clinical data--> |
<!--Clinical data--> |
||
Line 12: | Line 13: | ||
| pregnancy_category = |
| pregnancy_category = |
||
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
||
| legal_CA = |
| 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 = |
||
Line 28: | Line 30: | ||
| 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 = |
||
Line 33: | Line 37: | ||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
||
| DrugBank = |
| DrugBank = |
||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|||
| ChemSpiderID = 8495084 |
|||
<!--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 |
||
| 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 |
|||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|||
| StdInChIKey = QWHSUXWDDKWTOG-UHFFFAOYSA-N |
|||
}} |
}} |
||
'''JWH-198''' is a drug from the [[aminoalkylindole]] |
'''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 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> |
|||
⚫ | |||
⚫ | |||
* [[JWH-081]] |
* [[JWH-081]] |
||
* [[JWH-193]] |
* [[JWH-193]] |
||
==References== |
== References == |
||
{{Reflist}} |
{{Reflist}} |
||
Line 54: | Line 66: | ||
[[Category:Aminoalkylindoles]] |
[[Category:Aminoalkylindoles]] |
||
[[Category:Naphthoylindoles]] |
[[Category:Naphthoylindoles]] |
||
[[Category: |
[[Category:4-Morpholinyl compounds]] |
||
[[Category:Designer drugs]] |
|||
[[Category:CB1 receptor agonists]] |
|||
{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
Latest revision as of 13:18, 10 July 2023
Legal status | |
---|---|
Legal status |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C26H26N2O3 |
Molar mass | 414.505 g·mol−1 |
3D model (JSmol) | |
| |
| |
(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]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ : Schedules of controlled substances