RCS-4
- CA: Schedule II
- DE: Anlage II (Authorized trade only, not prescriptible)
- UK: Class B
- US: Schedule I
- Illegal in Sweden, I-N (Poland)[1]
- 2-(4-methoxyphenyl)-1-(1-pentyl-indol-3-yl)methanone
- 1345966-78-0 N
- 24769418 Y
- Y6911BZ2UL
- DTXSID70158820
- Interactive image
- CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC
- InChI=1S/C21H23NO2/c1-3-4-7-14-22-15-19(18-8-5-6-9-20(18)22)21(23)16-10-12-17(24-2)13-11-16/h5-6,8-13,15H,3-4,7,14H2,1-2H3 Y
- Key:OZCYJKDWRUIFFE-UHFFFAOYSA-N Y
RCS-4, or 1-pentyl-3-(4-methoxybenzoyl)indole, is a synthetic cannabinoid drug sold under the names SR-19, BTM-4, or Eric-4 (later shortened to E-4), but originally, OBT-199.
Pharmacology
RCS-4 is a potent cannabinoid receptor agonist, with EC50 values of 146 nM for human CB1 receptors, and 46 nM for human CB2 receptors.[2] All methoxyphenyl regioisomers, and N-butyl homologues of RCS-4 and its regioisomers also display potent agonist activities at CB1 and CB2 receptors.[2]
Legality
RCS-4 was banned in Sweden on 1 October 2010 as a hazardous good harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.[3][4]
It was outlawed in Denmark on 11 March 2011.[5]
In August 2011, New Zealand added not only RCS-4 but also its 1-butyl homologue, and the 2-methoxybenzoyl isomers of both these compounds, to a temporary class drug schedule (i.e. equivalent to Class C but reviewed after 12 months, and with personal possession and use of small amounts decriminalised), which was newly created under the Misuse of Drugs Amendment Act 2011 passed a week earlier.[6][7][8]
As of October 2015 RCS-4 is a controlled substance in China.[9]
See also
- AM-630
- AM-679
- RCS-8
- Pravadoline (WIN 48,098)
- Structural scheduling of synthetic cannabinoids
References
- ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 12 June 2011.
- ^ a b Banister SD, Stuart J, Conroy T, Longworth M, Manohar M, Beinat C, et al. (2015). "Structure–activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues". Forensic Toxicology. 33 (2): 355–366. doi:10.1007/s11419-015-0282-9. S2CID 33994750.
- ^ Swedish Code of Statutes Regulation (2010:1086).
- ^ Swedish Code of Statutes Regulation (2010:1086). (pdf) Archived 2011-07-28 at the Wayback Machine
- ^ "Bilag 1 - Liste over euforiserende midler omfattet af bekendtgørelsen". Ministeriet for Sundhed og Forebyggelse. Archived from the original on 4 March 2016.
- ^ "Kronic ban passed by Parliament". The New Zealand Herald. NZPA. 4 August 2011. Retrieved 4 November 2011.
- ^ "Synthetic cannabis off shelves by Wednesday". The New Zealand Herald. NZPA. 9 August 2011. Retrieved 4 November 2011.
- ^ New Zealand Gazette. Tuesday 9 August 2011. Issue No 122, pp 3365-3366. Departmental Notices. Health. Misuse of Drugs Act 1975. Temporary Class Drug Notice.
- ^ "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. Retrieved 1 October 2015.
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(comparison)
Cannabibutols |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
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Miscellaneous cannabinoids |
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Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids (dibenzopyrans) |
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Non-classical cannabinoids |
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Adamantoylindoles |
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Benzimidazoles | |
Benzoylindoles |
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Eicosanoids |
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Hydrocarbons | |
Indazole carboxamides | |
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Indole-3-carboxylates | |
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Naphthoylindoles |
|
Naphthoylpyrroles | |
Naphthylmethylindenes | |
Naphthylmethylindoles | |
Phenylacetylindoles | |
Pyrazolecarboxamides |
|
Pyrrolobenzoxazines | |
Quinolinyl esters | |
Tetramethylcyclo- propanoylindazoles | |
Tetramethylcyclo- propanoylindoles | |
Tetramethylcyclo- propylindoles | |
Others |
|
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics