Chemistry:MAM-2201
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| Formula | C25H24FNO |
| Molar mass | 373.471 g·mol−1 |
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MAM-2201 (4'-methyl-AM-2201, 5"-fluoro-JWH-122) is a drug that presumably acts as a potent agonist for the cannabinoid receptors.[1][2] 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.[3][4][5] 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.[6] 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.[7]
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.[8]
MAM-2201 has been banned by being added to the temporary class drug schedule in New Zealand, effective from 13 July 2012.[9]
As of October 2015 MAM-2201 is a controlled substance in China.[10]
See also
References
- ↑ "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. November 2015. doi:10.1007/s00414-015-1257-4. PMID 26349566.
- ↑ "Targeted and non-targeted metabolite identification of MAM-2201 in human, mouse, and rat hepatocytes". Drug Testing and Analysis 10 (8): 1328–1335. April 2018. doi:10.1002/dta.2389. PMID 29608249.
- ↑ EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA
- ↑ "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. July 2012. doi:10.1016/j.forsciint.2011.12.010. PMID 22264627.
- ↑ "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. July 2012. doi:10.1007/s00216-012-6122-4. PMID 22710567.
- ↑ "Metabolome disruption of the rat cerebrum induced by the acute toxic effects of the synthetic cannabinoid MAM-2201". Life Sciences 137: 49–55. September 2015. doi:10.1016/j.lfs.2015.05.013. PMID 26032255.
- ↑ "Finding order in chemical chaos - Continuing characterization of synthetic cannabinoid receptor agonists". Neuropharmacology 134 (Pt A): 73–81. May 2018. doi:10.1016/j.neuropharm.2017.10.041. PMID 29113898.
- ↑ : 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. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
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