NM-2201 Legal status
CA : Schedule II
DE : Anlage II (Authorized trade only, not prescriptible)
UK : Class B
US : Schedule I
Illegal in Sweden
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 ) 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 .[1] [2] [3] [4]
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.[5] It has been linked to serious adverse events in users.[6]
Legal status [ ]
NM-2201 is specifically banned in Sweden,[7] Germany (Anlage II ),[8] and Japan[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.[10]
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.[10]
See also [ ]
References [ ]
^ 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 .
Cannabinoids
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Delta-9-THC (THC)
THCH
THCP
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Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoids
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AM-2201
AM-694
WIN-55,212-2
Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
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See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG
2-AGE (noladin ether)
11-Hydroxy-THC
α-Amyrin · β-Amyrin
AB-CHMINACA
AM-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
Gallocatechol (gallocatechin)
Honokiol
HU-210
JWH-007
JWH-015
JWH-018
JWH-073
Kavain
L-759,633
Levonantradol
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Nabilone
Nabitan
NADA
O-1812
Oleamide
Pravadoline
Serinolamide A
THC (dronabinol)
UR-144
WIN 55,212-2
Yangonin
CB2
Agonists: 2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Virodhamine
NAGly (GPR18 )
Agonists: Abnormal cannabidiol
ACPA
AM251
Anandamide
Cannabidiol
NADGly
THC (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
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THC (dronabinol)
GPR119 Unsorted
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AM-404
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Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
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JZL-184
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URB-602
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Inhibitors: Betulinic acid
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Orlistat (tetrahydrolipstatin)
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Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)