5F-CUMYL-PINACA Legal status
CA : Schedule II
DE : NpSG (Industrial and scientific use only)
UK : Under Psychoactive Substances Act
US : Schedule I
Illegal in Sweden
1-(5-Fluoropentyl)-N -(2-phenylpropan-2-yl)-1H -indazole-3-carboxamide
CAS Number 1400742-16-6 Y PubChem CID ChemSpider UNII Formula C 22 H 26 F N 3 O Molar mass 367.468 g·mol−1 3D model (JSmol )
O=C(NC(C)(C)C1=CC=CC=C1)C2=NN(CCCCCF)C3=C2C=CC=C3
InChI=1S/C22H26FN3O/c1-22(2,17-11-5-3-6-12-17)24-21(27)20-18-13-7-8-14-19(18)26(25-20)16-10-4-9-15-23/h3,5-8,11-14H,4,9-10,15-16H2,1-2H3,(H,24,27)
Key:XSHGVIPHMOTDCS-UHFFFAOYSA-N
5F-CUMYL-PINACA (also known as SGT-25 and sometimes sold in e-cigarette form as C-Liquid )[1] is an indazole -3-carboxamide based synthetic cannabinoid .[2] 5F-CUMYL-PINACA acts as a potent agonist for the cannabinoid receptors , with the original patent claiming approximately 4x selectivity for CB1 , having an EC50 of <0.1 nM for human CB1 receptors and 0.37 nM for human CB2 receptors .[3] In more recent assays using different techniques, 5F-CUMYL-PINACA was variously found to have an EC50 of 0.43 nM at CB1 and 11.3 nM at CB2 , suggesting a somewhat higher CB1 selectivity of 26 times,[4] or alternatively 15.1 nM at CB1 and 34.8 nM at CB2 with only 2.3 times selectivity, however these figures cannot be directly compared due to the different assay techniques used in each case.[5]
Legal status [ ]
In the United States, 5F-CUMYL-PINACA became a Schedule I Controlled Substance in 2019.[6]
Sweden's public health agency suggested classifying 5F-CUMYL-PINACA as a hazardous substance on November 10, 2014.[7]
See also [ ]
References [ ]
^ Angerer V, Franz F, Moosmann B, Bisel P, Auwärter V (13 November 2018). "5F-Cumyl-PINACA in 'e-liquids' for electronic cigarettes: comprehensive characterization of a new type of synthetic cannabinoid in a trendy product including investigations on the in vitro and in vivo phase I metabolism of 5F-Cumyl-PINACA and its non-fluorinated analog Cumyl-PINACA" . Forensic Toxicology . 37 (1): 186–196. doi :10.1007/s11419-018-0451-8 . PMC 6315005 . PMID 30636986 .
^ "5-fluoro CUMYL-PINACA (CRM)" . Cayman Chemical. Retrieved 22 November 2018 .
^ Bowden; et al. (11 April 2013). "Patent WO 2014167530 - Cannabinoid compounds" . New Zealand Patent application 623626 . Retrieved 22 November 2018 .
^ Longworth M, Banister SD, Boyd R, Kevin RC, Connor M, McGregor IS, Kassiou M (October 2017). "Pharmacology of Cumyl-Carboxamide Synthetic Cannabinoid New Psychoactive Substances (NPS) CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA, and Their Analogues". ACS Chemical Neuroscience . 8 (10): 2159–2167. doi :10.1021/acschemneuro.7b00267 . PMID 28792725 .
^ Asada A, Doi T, Tagami T, Takeda A, Satsuki Y, Kawaguchi M, Nakamura A, Sawabe Y (January 2018). "Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids". Forensic Toxicology . 36 (1): 170–177. doi :10.1007/s11419-017-0374-9 . ISSN 1860-8965 . S2CID 7996915 .
^ "Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I" . Federal Register.
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids suggested classified as health endangering substance] (in Swedish). Public Health Agency of Sweden . 10 November 2014. Retrieved 11 July 2015 .
Cannabinoids
Phytocannabinoids
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Delta-9-THC (THC)
THCH
THCP
THCV
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
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes
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
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
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
Menabitan
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
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
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)