NM-2201
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name = Naphthalen-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate
| image = NM-2201_structure.png
| width = 150
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA = Schedule II
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US = Schedule I
| legal_status = Illegal in Sweden
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2042201-16-9
| ATC_prefix =
| ATC_suffix =
| PubChem = 91864534
| ChemSpiderID = 30922478
| smiles = FCCCCCN1C=C(C(OC2=C(C=CC=C3)C3=CC=C2)=O)C4=CC=CC=C41
| StdInChI = 1S/C24H22FNO2/c25-15-6-1-7-16-26-17-21(20-12-4-5-13-22(20)26)24(27)28-23-14-8-10-18-9-2-3-11-19(18)23/h2-5,8-14,17H,1,6-7,15-16H2
| StdInChIKey = PRGFSQYZCKCBQO-UHFFFAOYSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CCQ6IR3CU2
| C=24 | H=22 | F=1 | N=1 | O=2
}}
NM-2201 (also known as CBL-2201 and NA-5F-PIC{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming synthetic cannabinoids | journal = Drug Testing and Analysis | volume = 15 | issue = 3 | pages = 255–276 | date = March 2023 | pmid = 36346325 | doi = 10.1002/dta.3403 }}) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low nanomolar affinity.{{cite journal | vauthors = Kondrasenko AA, Goncharov EV, Dugaev KP, Rubaylo AI | title = CBL-2201. Report on a new designer drug: Napht-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate | journal = Forensic Science International | volume = 257 | pages = 209–213 | date = December 2015 | pmid = 26386336 | doi = 10.1016/j.forsciint.2015.08.023 }}{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15334 | title=NM-2201 | publisher=Cayman Chemical | access-date=9 July 2015}}{{cite journal | vauthors = Namera A, Kawamura M, Nakamoto A, Saito T, Nagao M | title = Comprehensive review of the detection methods for synthetic cannabinoids and cathinones | journal = Forensic Toxicology | volume = 33 | issue = 2 | pages = 175–194 | year = 2015 | pmid = 26257831 | pmc = 4525208 | doi = 10.1007/s11419-015-0270-0 }}{{cite journal | vauthors = Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Baranovsky A, Shafran Y | title = Synthetic cannabinoids as designer drugs: new representatives of indol-3-carboxylates series and indazole-3-carboxylates as novel group of cannabinoids. Identification and analytical data | journal = Forensic Science International | volume = 244 | pages = 263–75 | date = November 2014 | pmid = 25305529 | doi = 10.1016/j.forsciint.2014.09.013 }}
Pharmacology
NM-2201 acts as a full agonist with a binding affinity of 0.332 nM at CB1 and 0.732 nM at CB2 cannabinoid receptors.{{cite journal | vauthors = Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE | title = Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice | journal = Forensic Toxicology | volume = 34 | issue = 2 | pages = 329–343 | year = 2016 | pmid = 27429655 | pmc = 4929166 | doi = 10.1007/s11419-016-0320-2 }} It has been linked to serious adverse events in users.{{cite journal | vauthors = Samra K, Boon IS, Packer G, Jacob S | title = black mamba | journal = BMJ Case Reports | volume = 2017 | pages = bcr–2016–218431 | date = April 2017 | pmid = 28433979 | pmc = 5534782 | doi = 10.1136/bcr-2016-218431 }}
Legal status
NM-2201 is specifically banned in Sweden,{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassade som hälsofarlig vara | trans-title = Cannabinoids are proposed to be classified as a health hazard | publisher=Folkhälsomyndigheten (The Public Health Authority) | access-date=9 July 2015 | language=sv}} Germany (Anlage II),{{Cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html|title=Gesetz über den Verkehr mit Betäubungsmitteln Anlage II | trans-title = Law on the Traffic in Narcotics Annex II |website=www.gesetze-im-internet.de|publisher=Bundesministerium der Justiz und für Verbraucherschutz|language=de|access-date=24 October 2016}} and Japan{{cite journal | vauthors = Diao X, Carlier J, Zhu M, Pang S, Kronstrand R, Scheidweiler KB, Huestis MA | title = In vitro and in vivo human metabolism of a new synthetic cannabinoid NM-2201 (CBL-2201) | journal = Forensic Toxicology | volume = 35 | issue = 1 | pages = 20–32 | date = January 2017 | pmid = 28286577 | pmc = 5342258 | doi = 10.1007/s11419-016-0326-9 }} but is also controlled in many other jurisdictions under analogue laws.
On May 30, 2018 the United States Drug Enforcement Administration, Department of Justice published a notice of intent to place NM-2201 and 4 other synthetic cannabinoids in schedule I of the Controlled Substances Act. This notice went into effect on June 29, 2018.
Use
NM-2201 was linked to an incident in December 2015 where 25-30 people in Ocala, FL were taken to hospitals after experiencing seizures.{{Cite web|url=https://www.deadiversion.usdoj.gov/fed_regs/rules/2018/fr0530.htm|title=2018 - Temporary Placement of NM2201, 5F-AB-PINACA, 4-CN-CUMYL-BUTINACA, MMB-CHMICA and 5F-CUMYL-P7AICA Into Schedule I|website=www.deadiversion.usdoj.gov|language=en-US|access-date=2018-06-15}}
See also
References
{{Reflist}}
{{Cannabinoids}}
{{Cannabinoidergics}}