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Importing Wikidata short description: "Chemical compound"
 
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{{Short description|Chemical compound}}
{{redirect|NRG-4|the protein growth factor|Neuregulin 4}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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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_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = Class B
| legal_US = Schedule I
| legal_US = Schedule I
| legal_DE = Anlage II
| legal_DE = Anlage II
| legal_status = Illegal in Sweden, I-N (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | accessdate = 12 June 2011}}</ref>
| legal_status = Illegal in Sweden, I-N (Poland)<ref>{{cite web | title = Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 ) | url = http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614 | publisher = Internetowy System Aktów Prawnych | access-date = 12 June 2011}}</ref>


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1345966-78-0
| CAS_number = 1345966-78-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y6911BZ2UL
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24769418
| ChemSpiderID = 24769418
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<!--Chemical data-->
<!--Chemical data-->
| C=21 | H=23 | N=1 | O=2
| C=21 | H=23 | N=1 | O=2
| molecular_weight = 321.413 g/mol
| smiles = CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC
| smiles = CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OZCYJKDWRUIFFE-UHFFFAOYSA-N
| StdInChIKey = OZCYJKDWRUIFFE-UHFFFAOYSA-N
}}
}}
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==Pharmacology==
==Pharmacology==
RCS-4 is a potent cannabinoid receptor agonist, with EC<sub>50</sub> values of 146 nM for human CB<sub>1</sub> receptors, and 46 nM for human CB<sub>2</sub> receptors.<ref name = "Forensic Toxicol 2015">{{Cite journal | doi = 10.1007/s11419-015-0282-9| title = Structure–activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues| journal = Forensic Toxicology| volume = 33| issue = 2| pages = 355| year = 2015| last1 = Banister | first1 = S. D. | last2 = Stuart | first2 = J. | last3 = Conroy | first3 = T. | last4 = Longworth | first4 = M. | last5 = Manohar | first5 = M. | last6 = Beinat | first6 = C. | last7 = Wilkinson | first7 = S. M. | last8 = Kevin | first8 = R. C. | last9 = Hibbs | first9 = D. E. | last10 = Glass | first10 = M. | last11 = Connor | first11 = M. | last12 = McGregor | first12 = I. S. | last13 = Kassiou | first13 = M. }}</ref> All methoxyphenyl regioisomers, and ''N''-butyl homologues of RCS-4 and its regioisomers also display potent agonist activities at CB<sub>1</sub> and CB<sub>2</sub> receptors.<ref name = "Forensic Toxicol 2015" />
RCS-4 is a potent cannabinoid receptor agonist, with EC<sub>50</sub> values of 146 nM for human CB<sub>1</sub> receptors, and 46 nM for human CB<sub>2</sub> receptors.<ref name = "Forensic Toxicol 2015">{{Cite journal | vauthors = Banister SD, Stuart J, Conroy T, Longworth M, Manohar M, Beinat C, Wilkinson SM, Kevin RC, Hibbs DE, Glass M, Connor M | s2cid = 33994750 | display-authors = 6 | doi = 10.1007/s11419-015-0282-9| title = Structure–activity relationships of synthetic cannabinoid designer drug RCS-4 and its regioisomers and C4 homologues| journal = Forensic Toxicology| volume = 33| issue = 2| pages = 355–366| year = 2015 | url = https://zenodo.org/record/47807 }}</ref> All methoxyphenyl regioisomers, and ''N''-butyl homologues of RCS-4 and its regioisomers also display potent agonist activities at CB<sub>1</sub> and CB<sub>2</sub> receptors.<ref name = "Forensic Toxicol 2015" />


==Legality==
==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.<ref>[http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]</ref><ref>[http://www.lagboken.se/files/SFS/2010/101086.PDF Swedish Code of Statutes Regulation (2010:1086). (pdf)]</ref>
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.<ref>[http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1999:58 Swedish Code of Statutes Regulation (2010:1086).]</ref><ref>[http://www.lagboken.se/files/SFS/2010/101086.PDF Swedish Code of Statutes Regulation (2010:1086). (pdf)] {{webarchive|url=https://web.archive.org/web/20110728111705/http://www.lagboken.se/files/SFS/2010/101086.PDF |date=2011-07-28 }}</ref>


It was outlawed in Denmark on 11 March 2011.<ref>http://laegemiddelstyrelsen.dk/~/media/AC4F04EB48F74523A76BA84DAB9B6067.ashx</ref>
It was outlawed in Denmark on 11 March 2011.<ref>{{cite web | title = Bilag 1 - Liste over euforiserende midler omfattet af bekendtgørelsen | url = http://laegemiddelstyrelsen.dk/~/media/AC4F04EB48F74523A76BA84DAB9B6067.ashx | archive-url = https://web.archive.org/web/20160304231106/https://laegemiddelstyrelsen.dk/~/media/AC4F04EB48F74523A76BA84DAB9B6067.ashx | archive-date = 4 March 2016 | publisher = Ministeriet for Sundhed og Forebyggelse }}</ref>


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.<ref name="NZ_Herald_10742964">{{cite news |url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10742964 |title=Kronic ban passed by Parliament |date=4 August 2011 |agency=[[NZPA]] |work=[[The New Zealand Herald]] |accessdate=4 November 2011}}</ref><ref name="NZ_Herald_10743976">{{cite news |url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10743976 |title=Synthetic cannabis off shelves by Wednesday |date=9 August 2011 |agency=[[NZPA]] |work=[[The New Zealand Herald]] |accessdate=4 November 2011}}</ref><ref>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.</ref>
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.<ref name="NZ_Herald_10742964">{{cite news |url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10742964 |title=Kronic ban passed by Parliament |date=4 August 2011 |agency=[[NZPA]] |work=[[The New Zealand Herald]] |access-date=4 November 2011}}</ref><ref name="NZ_Herald_10743976">{{cite news |url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10743976 |title=Synthetic cannabis off shelves by Wednesday |date=9 August 2011 |agency=[[NZPA]] |work=[[The New Zealand Herald]] |access-date=4 November 2011}}</ref><ref>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.</ref>


As of October 2015 RCS-4 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>
As of October 2015 RCS-4 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015}}</ref>


[[Image:RCS4-analogues.png|300px|thumb|none|RCS-4 and related analogues detected in synthetic cannabis blends]]
[[Image:RCS4-analogues.png|300px|thumb|none|RCS-4 and related analogues detected in synthetic cannabis blends]]


==See also==
== See also ==
*[[AM-630]]
*[[AM-630]]
*[[AM-679 (cannabinoid)|AM-679]]
*[[AM-679 (cannabinoid)|AM-679]]
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*[[Structural scheduling of synthetic cannabinoids]]
*[[Structural scheduling of synthetic cannabinoids]]


==References==
== References ==
{{reflist}}
<references/>


{{cannabinoids}}
{{cannabinoids}}

Latest revision as of 16:00, 10 July 2022

"NRG-4" redirects here. For the protein growth factor, see Neuregulin 4.
RCS-4
Legal status
Legal status
Identifiers
  • 2-(4-methoxyphenyl)-1-(1-pentyl-indol-3-yl)methanone
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.383 Edit this at Wikidata
Chemical and physical data
FormulaC21H23NO2
Molar mass321.420 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:OZCYJKDWRUIFFE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

[edit]

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

[edit]

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]

RCS-4 and related analogues detected in synthetic cannabis blends

See also

[edit]

References

[edit]
  1. ^ "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.
  2. ^ 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.
  3. ^ Swedish Code of Statutes Regulation (2010:1086).
  4. ^ Swedish Code of Statutes Regulation (2010:1086). (pdf) Archived 2011-07-28 at the Wayback Machine
  5. ^ "Bilag 1 - Liste over euforiserende midler omfattet af bekendtgørelsen". Ministeriet for Sundhed og Forebyggelse. Archived from the original on 4 March 2016.
  6. ^ "Kronic ban passed by Parliament". The New Zealand Herald. NZPA. 4 August 2011. Retrieved 4 November 2011.
  7. ^ "Synthetic cannabis off shelves by Wednesday". The New Zealand Herald. NZPA. 9 August 2011. Retrieved 4 November 2011.
  8. ^ 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.
  9. ^ "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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