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Chemical compound
NM-2201
Legal status
Naphthalen-1-yl 1-(5-fluoropentyl)-1H -indole-3-carboxylate
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 24 H 22 F N O 2
Molar mass 375.443 g·mol−1 3D model (
JSmol )
FCCCCCN1C=C(C(OC2=C(C=CC=C3)C3=CC=C2)=O)C4=CC=CC=C41
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]
See also
References
^ Pulver, Benedikt; Fischmann, Svenja; Gallegos, Ana; Christie, Rachel (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis . 15 (3): 255–276.
doi :
10.1002/dta.3403 .
^ 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" (in Swedish). Folkhälsomyndigheten. Retrieved 9 July 2015 .
^
"Gesetz über den Verkehr mit Betäubungsmitteln Anlage 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, Huestis MA (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 .
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