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Chemical compound
CUMYL-FUBINACA Legal status
DE : NpSG (Industrial and scientific use only)
UK : Class B
1-[(4-fluorophenyl)methyl]-N-(2-phenylpropan-2-yl)indazole-3-carboxamide
CAS Number Formula C 24 H 22 F N 3 O Molar mass 387.458 g·mol−1 3D model (JSmol )
CC(C)(C1=CC=CC=C1)NC(=O)C2=NN(C3=CC=CC=C32)CC4=CC=C(C=C4)F
InChI=1S/C24H22FN3O/c1-24(2,18-8-4-3-5-9-18)26-23(29)22-20-10-6-7-11-21(20)28(27-22)16-17-12-14-19(25)15-13-17/h3-15H,16H2,1-2H3,(H,26,29)
Key:ABBDMPBQHOHMJZ-UHFFFAOYSA-N
CUMYL-FUBINACA (SGT-149 ) is an indazole -3-carboxamide based synthetic cannabinoid receptor agonist, with an EC50 of 1.8nM for human CB1 receptors and 23.7nM for human CB2 receptors , giving it around 13x selectivity for CB1 .[ 1] [ 2] [ 3] [ 4] It has been sold online as a designer drug .[ 5]
^ WO 2014167530 , Bowden MW, Williamson PB, "Cannabinoid compounds", published 11 April 2013
^ 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 .
^ Banister SD, Connor M (2018). "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution". New Psychoactive Substances . Handbook of Experimental Pharmacology. Vol. 252. pp. 191–226. doi :10.1007/164_2018_144 . ISBN 978-3-030-10560-0 . PMID 30105473 .
^ Krishna Kumar K, Shalev-Benami M, Robertson MJ, Hu H, Banister SD, Hollingsworth SA, et al. (January 2019). "Structure of a Signaling Cannabinoid Receptor 1-G Protein Complex" . Cell . 176 (3): 448–458.e12. doi :10.1016/j.cell.2018.11.040 . PMC 6461403 . PMID 30639101 .
^ Thornton SL, Darracq MA, Gugelmann HM, Armenian P (2019). "Surface internet marketplace presence and availability of NPS sold as research chemicals: a snapshot study" . Toxicology Communications . 3 (1): 67–74. doi :10.1080/24734306.2019.1648067 . S2CID 202372196 .
Phytocannabinoids (comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Others
Allosteric CBR Tooltip Cannabinoid receptor ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
Receptor (ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
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-1172
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-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (GPR18 )
GPR55
GPR119
Transporter (modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (modulators )
Others
Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)