RCS-4

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.

RCS-4
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • Illegal in Sweden, I-N (Poland)[1]
Identifiers
IUPAC name
  • 2-(4-methoxyphenyl)-1-(1-pentyl-indol-3-yl)methanone
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.383
Chemical and physical data
FormulaC21H23NO2
Molar mass321.420 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCn1cc(c2c1cccc2)C(=O)c3ccc(cc3)OC
InChI
  • 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
 NY (what is this?)  (verify)

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]

RCS-4 and related analogues detected in synthetic cannabis blends

See also
  • AM-630
  • AM-679
  • RCS-8
  • Pravadoline (WIN 48,098)
  • Structural scheduling of synthetic cannabinoids

References
  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. 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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