en NM-2201

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 ;
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;

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]

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]

References

^ 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.
^ 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.
^ "NM-2201". Cayman Chemical. Retrieved 9 July 2015.
^ 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.
^ 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.
^ 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.
^ 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.
^ "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.
^ "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.
^ 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.
^ ^a ^b "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.

[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.

[:0-11] "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.

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NM-2201

Pharmacology

Legal status

Use

See also

References

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