NM-2201

NM-2201 (also known as CBL-2201 and NA-5F-PIC^[1]) 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.^[2][3][4][5]

NM-2201

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in Sweden
Identifiers
IUPAC name Naphthalen-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate
CAS Number	2042201-16-9 Y
PubChem CID	91864534
ChemSpider	30922478
UNII	CCQ6IR3CU2
CompTox Dashboard (EPA)	DTXSID201009986
Chemical and physical data
Formula	C24H22FNO2
Molar mass	375.443 g·mol−1
3D model (JSmol)	Interactive image
SMILES FCCCCCN1C=C(C(OC2=C(C=CC=C3)C3=CC=C2)=O)C4=CC=CC=C41
InChI InChI=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 Key:PRGFSQYZCKCBQO-UHFFFAOYSA-N

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.^[6] It has been linked to serious adverse events in users.^[7]

Legal status

NM-2201 is specifically banned in Sweden,^[8] Germany (Anlage II),^[9] and Japan^[10] 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.^[11]

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.^[11]

See also

• EAM-2201
• MAM-2201
• THJ-2201
• SDB-005

References

1. Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
2. Kondrasenko AA, Goncharov EV, Dugaev KP, Rubaylo AI (December 2015). "CBL-2201. Report on a new designer drug: Napht-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate". Forensic Science International. 257: 209–213. doi:10.1016/j.forsciint.2015.08.023. PMID 26386336.
3. "NM-2201". Cayman Chemical. Retrieved 9 July 2015.
4. Namera A, Kawamura M, Nakamoto A, Saito T, Nagao M (2015). "Comprehensive review of the detection methods for synthetic cannabinoids and cathinones". Forensic Toxicology. 33 (2): 175–194. doi:10.1007/s11419-015-0270-0. PMC 4525208. PMID 26257831.
5. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Baranovsky A, Shafran Y (November 2014). "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". Forensic Science International. 244: 263–75. doi:10.1016/j.forsciint.2014.09.013. PMID 25305529.
6. Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
7. Samra K, Boon IS, Packer G, Jacob S (April 2017). "black mamba". BMJ Case Reports. 2017: bcr–2016–218431. doi:10.1136/bcr-2016-218431. PMC 5534782. PMID 28433979.
8. "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard] (in Swedish). Folkhälsomyndigheten (The Public Health Authority). Retrieved 9 July 2015.
9. "Gesetz über den Verkehr mit Betäubungsmitteln Anlage II" [Law on the Traffic in Narcotics Annex II]. www.gesetze-im-internet.de (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved 24 October 2016.
10. Diao X, Carlier J, Zhu M, Pang S, Kronstrand R, Scheidweiler KB, et al. (January 2017). "In vitro and in vivo human metabolism of a new synthetic cannabinoid NM-2201 (CBL-2201)". Forensic Toxicology. 35 (1): 20–32. doi:10.1007/s11419-016-0326-9. PMC 5342258. PMID 28286577.
11. "2018 - Temporary Placement of NM2201, 5F-AB-PINACA, 4-CN-CUMYL-BUTINACA, MMB-CHMICA and 5F-CUMYL-P7AICA Into Schedule I". www.deadiversion.usdoj.gov. Retrieved 2018-06-15.