MAM-2201

MAM-2201
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (1-(5-Fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)methanone;
CAS Number	1354631-24-5 ;
PubChem CID	66570720;
ChemSpider	28289977;
UNII	P4KP9PRG29;
KEGG	C22772;
CompTox Dashboard (EPA)	DTXSID20159387 ;
ECHA InfoCard	100.257.545
Chemical and physical data
Formula	C25H24FNO
Molar mass	373.471 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FCCCCCn(c4)c2ccccc2c4C(=O)c3ccc(C)c1ccccc13;
	InChI InChI=1S/C25H24FNO/c1-18-13-14-22(20-10-4-3-9-19(18)20)25(28)23-17-27(16-8-2-7-15-26)24-12-6-5-11-21(23)24/h3-6,9-14,17H,2,7-8,15-16H2,1H3; Key:IGBHZHCGWLHBAE-UHFFFAOYSA-N;

MAM-2201 (4'-methyl-AM-2201, 5"-fluoro-JWH-122) is a drug that presumably acts as a potent agonist for the cannabinoid receptors.^[2]^[3] It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in the Netherlands and Germany in June 2011 as an ingredient in synthetic cannabis smoking blends.^[4]^[5]^[6] Like RCS-4 and AB-001, MAM-2201 thus appears to be a novel compound invented by "research chemical" suppliers specifically for grey-market recreational use. Structurally, MAM-2201 is a hybrid of two known cannabinoid compounds JWH-122 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

A study of MAM-2201 in rats showed that it causes neurofunctional disruptions.^[7] A later study demonstrated that MAM-2201 bound to and activated human CB1 and CB2 cannabinoid receptors and substituted for THC in THC drug discrimination in mice.^[8]

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as MAM-2201 are Schedule I Controlled Substances.^[9]

MAM-2201 has been banned by being added to the temporary class drug schedule in New Zealand, effective from 13 July 2012.^[10]

As of October 2015 MAM-2201 is a controlled substance in China.^[11]

References

^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
^ Zaitsu K, Nakayama H, Yamanaka M, Hisatsune K, Taki K, Asano T, et al. (November 2015). "High-resolution mass spectrometric determination of the synthetic cannabinoids MAM-2201, AM-2201, AM-2232, and their metabolites in postmortem plasma and urine by LC/Q-TOFMS". International Journal of Legal Medicine. 129 (6): 1233–45. doi:10.1007/s00414-015-1257-4. PMID 26349566. S2CID 24905067.
^ Kim JH, Kong TY, Moon JY, Choi KH, Cho YY, Kang HC, et al. (April 2018). "Targeted and non-targeted metabolite identification of MAM-2201 in human, mouse, and rat hepatocytes". Drug Testing and Analysis. 10 (8): 1328–1335. doi:10.1002/dta.2389. PMID 29608249.
^ EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
^ Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V (July 2012). "Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system". Forensic Science International. 220 (1–3): e17-22. doi:10.1016/j.forsciint.2011.12.010. PMID 22264627.
^ Simolka K, Lindigkeit R, Schiebel HM, Papke U, Ernst L, Beuerle T (July 2012). "Analysis of synthetic cannabinoids in "spice-like" herbal highs: snapshot of the German market in summer 2011". Analytical and Bioanalytical Chemistry. 404 (1): 157–71. doi:10.1007/s00216-012-6122-4. PMID 22710567. S2CID 24068469.
^ Zaitsu K, Hayashi Y, Suzuki K, Nakayama H, Hattori N, Takahara R, et al. (September 2015). "Metabolome disruption of the rat cerebrum induced by the acute toxic effects of the synthetic cannabinoid MAM-2201". Life Sciences. 137: 49–55. doi:10.1016/j.lfs.2015.05.013. PMID 26032255.
^ Marusich JA, Wiley JL, Lefever TW, Patel PR, Thomas BF (May 2018). "Finding order in chemical chaos - Continuing characterization of synthetic cannabinoid receptor agonists". Neuropharmacology. 134 (Pt A): 73–81. doi:10.1016/j.neuropharm.2017.10.041. PMC 5934329. PMID 29113898.
^ 21 U.S.C. § 812: Schedules of controlled substances
^ Temporary Class Drug Notice, 5 July 2012. NZ Department of Internal Affairs.
^ "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.

[1] Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.

[2] Zaitsu K, Nakayama H, Yamanaka M, Hisatsune K, Taki K, Asano T, et al. (November 2015). "High-resolution mass spectrometric determination of the synthetic cannabinoids MAM-2201, AM-2201, AM-2232, and their metabolites in postmortem plasma and urine by LC/Q-TOFMS". International Journal of Legal Medicine. 129 (6): 1233–45. doi:10.1007/s00414-015-1257-4. PMID 26349566. S2CID 24905067.

[3] Kim JH, Kong TY, Moon JY, Choi KH, Cho YY, Kang HC, et al. (April 2018). "Targeted and non-targeted metabolite identification of MAM-2201 in human, mouse, and rat hepatocytes". Drug Testing and Analysis. 10 (8): 1328–1335. doi:10.1002/dta.2389. PMID 29608249.

[4] EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA

[5] Moosmann B, Kneisel S, Girreser U, Brecht V, Westphal F, Auwärter V (July 2012). "Separation and structural characterization of the synthetic cannabinoids JWH-412 and 1-[(5-fluoropentyl)-1H-indol-3yl]-(4-methylnaphthalen-1-yl)methanone using GC-MS, NMR analysis and a flash chromatography system". Forensic Science International. 220 (1–3): e17-22. doi:10.1016/j.forsciint.2011.12.010. PMID 22264627.

[6] Simolka K, Lindigkeit R, Schiebel HM, Papke U, Ernst L, Beuerle T (July 2012). "Analysis of synthetic cannabinoids in "spice-like" herbal highs: snapshot of the German market in summer 2011". Analytical and Bioanalytical Chemistry. 404 (1): 157–71. doi:10.1007/s00216-012-6122-4. PMID 22710567. S2CID 24068469.

[7] Zaitsu K, Hayashi Y, Suzuki K, Nakayama H, Hattori N, Takahara R, et al. (September 2015). "Metabolome disruption of the rat cerebrum induced by the acute toxic effects of the synthetic cannabinoid MAM-2201". Life Sciences. 137: 49–55. doi:10.1016/j.lfs.2015.05.013. PMID 26032255.

[8] Marusich JA, Wiley JL, Lefever TW, Patel PR, Thomas BF (May 2018). "Finding order in chemical chaos - Continuing characterization of synthetic cannabinoid receptor agonists". Neuropharmacology. 134 (Pt A): 73–81. doi:10.1016/j.neuropharm.2017.10.041. PMC 5934329. PMID 29113898.

[9] 21 U.S.C. § 812: Schedules of controlled substances

[10] Temporary Class Drug Notice, 5 July 2012. NZ Department of Internal Affairs.

[11] "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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Legal status

See also

References