5F-ADB - Wikipedia

Chemical compound Pharmaceutical compound 5F-ADB

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I
Identifiers
IUPAC name Methyl (S)-2-[1-(5-fluoropentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate
CAS Number	1715016-75-3
PubChem CID	101895417
ChemSpider	32741709
UNII	FD7BD1M9FY UN52BPP7RB(racemate)
KEGG	C22801
CompTox Dashboard (EPA)	DTXSID201009974
ECHA InfoCard	100.257.468
Chemical and physical data
Formula	C20H28FN3O3
Molar mass	377.460 g·mol−1
3D model (JSmol)	Interactive image
SMILES FCCCCC[N]2C1=CC=CC=C1C(=N2)C(=O)N[C@H](C(=O)OC)C(C)(C)C
InChI InChI=1S/C20H28FN3O3/c1-20(2,3)17(19(26)27-4)22-18(25)16-14-10-6-7-11-15(14)24(23-16)13-9-5-8-12-21/h6-7,10-11,17H,5,8-9,12-13H2,1-4H3,(H,22,25)/t17-/m1/s1 Key:PWEKNGSNNAKWBL-QGZVFWFLSA-N

5F-ADB (also known as MDMB-5F-PINACA using systematic EMCDDA nomenclature[2] and 5F-MDMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products and has been sold online as a designer drug.[3][4] 5F-ADB is a potent agonist of the CB1 receptor,[5] though it is unclear whether it is selective for this target.

5F-ADB was first identified in November 2014 from post-mortem samples taken from an individual who had died after using a product containing this substance. Subsequent testing identified 5F-ADB to have been present in a total of ten people who had died from unexplained drug overdoses in Japan between September 2014 and December 2014. 5F-ADB is believed to be extremely potent based on the very low levels detected in tissue samples, and appears to be significantly more toxic than earlier synthetic cannabinoid drugs that had previously been sold.[6]

In 2018, 5F-ADB was the most common synthetic cannabinoid to be identified in Drug Enforcement Administration seizures.[7] 5F-ADB was also identified in cannabidiol (CBD) products from a US-based CBD manufacturer in 2018.[8]

Deaths

[edit]

5F-MDMB-PINACA has been associated with 25 deaths in Europe between 2015 and 2017.[9]

Legal status

[edit]

In the United States, 5F-ADB is a schedule I controlled substance.[10]

5F-ADB was added to the Japanese banned drug list in December 2014.

See also

[edit]

The positional isomer, 4F-MDMB-PINACA has been characterised and is sometimes known as 4F-ADB,[11] despite "ADB" not having been used as a name for MDMB-PINACA. This is distinct from 4F-MDMB-BINACA which is a notable compound in its own right.

• 5F-AB-PINACA
• 5F-AMB
• 5F-APINACA
• AB-CHMINACA
• AB-FUBINACA
• AB-CHFUPYCA
• AB-PINACA
• ADB-BINACA
• ADB-CHMINACA
• ADB-FUBINACA
• ADB-PINACA
• ADBICA
• APICA
• APINACA
• MDMB-CHMICA
• MDMB-FUBINACA
• PX-3

References

[edit]

1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. ^ 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.
3. ^ Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, et al. (August 2015). "Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group". Analytical and Bioanalytical Chemistry. 407 (21): 6301–6315. doi:10.1007/s00216-015-8612-7. PMID 25893797. S2CID 31838655.
4. ^ Giorgetti A, Brunetti P, Pelotti S, Auwärter V (October 2022). "Detection of AP-237 and synthetic cannabinoids on an infused letter sent to a German prisoner". Drug Testing and Analysis. 14 (10): 1779–1784. doi:10.1002/dta.3351. PMC 9804899. PMID 35918775. S2CID 251281159.
5. ^ Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues". ACS Chemical Neuroscience. 7 (9): 1241–1254. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
6. ^ asegawa K, Wurita A, Minakata K, Gonmori K, Yamagishi I, Nozawa H, et al. (2014). "Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products". Forensic Toxicology. 33: 112–121. doi:10.1007/s11419-014-0259-0. S2CID 45508189.
7. ^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration. Archived from the original (PDF) on 2019-08-01. Retrieved 2019-08-01.
8. ^ Poklis JL, Mulder HA, Peace MR (January 2019). "The unexpected identification of the cannabimimetic, 5F-ADB, and dextromethorphan in commercially available cannabidiol e-liquids". Forensic Science International. 294: e25 – e27. doi:10.1016/j.forsciint.2018.10.019. PMC 6321772. PMID 30442388.
9. ^ European Monitoring Centre for Drugs and Drug Addiction, Europol (2017). 5F-MDMB-PINACA (PDF) (Report). Luxembourg: Publications Office of the European Union. doi:10.2810/210307.
10. ^ "Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I". Drug Enforcement Administration. Archived from the original on 2019-10-17. Retrieved 2017-03-17.
11. ^ Scientific Working Group for the Analysis of Seized Drugs. "4-Fluoro ADB monograph" (PDF). Scientific Working Group for the Analysis of Seized Drugs. Drug Enforcement Administration. Retrieved 29 January 2025.

v t e Cannabinoids
Phytocannabinoids(comparison)	Cannabibutols CBB Cannabichromenes CBC CBCA CBCA-A CBCB CBCBA CBCP CBCPA CBCV CBCVA CBCQ Cannabicyclols CBL CBLA CBLB CBLP CBLPA CBLV CBLVA Cannabidiols CBD CBDA CBD-C1 CBD-C5 CBDB CBDBA CBDD CBDH CBDP CBDPA CBDM CBDMA CBDV CBDVA CBDQ Cannabielsoins CBE CBEA CBEA-A CBEA-B CBEB CBEP CBEPA CBEV Cannabigerols CBG CBGA CBGB CBGBA CBGM CBGAM CBGP CBGPA CBNR CBNRA CBNRA-A CBGV CBGVA CBGVA-A CBGQ Cannabiphorols CBP Cannabinols CBN CBNA CBN-C1 CBN-C2 CBN-C4 CBNM CBND CBNDA CBNP CBNPA CBVD CBVDA Cannabitriols CBT CBTA CBTB CBTV CBTVA CBTP CBTPA Cannabivarins CBV CBVA Delta-3-tetrahydrocannabinols Delta-3-THC Delta-4-tetrahydrocannabinols Delta-4-THC Delta-7-tetrahydrocannabinols Delta-7-THC Delta-8-tetrahydrocannabinols Delta-8-THC Delta-8-THCA Delta-8-THCA-A Delta-8-THCB Delta-8-THCP Delta-8-THCV Delta-9-tetrahydrocannabinols Delta-9-THC (THC) THCA THCMA THCA-A THCA-B THCBA THCA-C4 THCC THCA-C1 THCA-A-C1 THCA-B-C1 THCB THCH THCP THCPA THCV THCVA THCQ Delta-10-Tetrahydrocannabinols Delta-10-THC Delta-11-Tetrahydrocannabinols Delta-11-THC Miscellaneous cannabinoids Δ8-iso-THC Δ4(8)-iso-THC 7,8-Dihydrocannabinol 8,9-Dihydrocannabidiol CBCF Cannabicitran CBF Cannabiglendol CBM CBR CBRPA Caryophyllene DCBF Alkylamides Epigallocatechin gallate Gallocatechol Hexahydrocannabinol (HHC) Perrottetinene Serinolamide A Yangonin Active metabolites 3'-OH-THC 7-OH-CBD 8,11-DiOH-THC 11-COOH-THC 11-OH-CBN 11-OH-HHC 11-OH-Δ8-THC 11-OH-Δ9-THC
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) 2-Arachidonoyl lysophosphatidylinositol (2-ALPI) 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)
Syntheticcannabinoidreceptoragonists /neocannabinoids	Classical cannabinoids(dibenzopyrans) 1,2-Didehydro-3-oxo-THCO 9-OH-HHC 9-Nor-9β-HHC A-40174 A-41988 A-42574 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-926 AM-938 AM-2389 AM-4030 AM-7438 AM-11245 AMG-1 AMG-3 AMG-36 AMG-41 Cis-THC CP 42,096 Dexanabinol (HU-211) DMHP Dronabinol HHCP-O-acetate HHCH HU-210 HU-243 Iso-THC JWH-051 JWH-056 JWH-057 JWH-065 JWH-091 JWH-102 JWH-103 JWH-124 JWH-130 JWH-133 JWH-138 JWH-139 JWH-142 JWH-143 JWH-161 JWH-186 JWH-187 JWH-188 JWH-189 JWH-190 JWH-191 JWH-215 JWH-216 JWH-217 JWH-224 JWH-225 JWH-226 JWH-227 JWH-229 JWH-230 JWH-233 JWH-247 JWH-254 JWH-256 JWH-277 JWH-278 JWH-298 JWH-299 JWH-300 JWH-301 JWH-310 JWH-336 JWH-338 JWH-339 JWH-340 JWH-341 JWH-349 JWH-350 JWH-352 JWH-353 JWH-354 JWH-355 JWH-356 JWH-357 JWH-358 JWH-359 JWH-360 JWH-361 JWH-362 KM-233 L-759,633 L-759,656 Levonantradol (CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 O-2365 O-2372 O-2373 O-2383 O-2426 O-2484 O-2545 O-2694 O-2715 O-2716 O-3223 O-3226 Parahexyl Pirnabine SP-111 THC hemisuccinate THC-O-acetate THC-O-phosphate THCP-O-acetate Non-classicalcannabinoids Cannabicyclohexanol Cannabinor CBD-DMH CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 Delta-6-Cannabidiol Etrinabdione HU-320 HU-331 HU-336 HU-345 HU-446 HU-465 HU-910 HUF-101 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 Onternabez (HU-308) SPA-229 Tinabinol Adamantoylindoles 5F-AKB-48 APICA STS-135 Benzimidazoles AZ-11713908 AZD-1940 BIM-018 FUBIMINA MCHB-1 PF-03550096 RQ-00202730 Benzoylindoles 1-Butyl-3-(2-methoxybenzoyl)indole 1-Butyl-3-(4-methoxybenzoyl)indole 1-Pentyl-3-(2-methoxybenzoyl)indole AM-630 AM-679 AM-694 AM-1241 AM-2233 GW-405,833 (L-768,242) Pravadoline RCS-4 WIN 54,461 Cyclohexylphenols CP-47,947 CP-55,940 Eicosanoids AM-883 AM-1346 ACEA ACPA Methanandamide (AM-356) O-585 O-689 O-1812 O-1860 O-1861 Indazole-3-carboxamides 4F-MDMB-BINACA 4'Cl-CUMYL-PINACA 4'F-CUMYL-5F-PINACA 5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-EDMB-PINACA 5F-EMB-PINACA A-CHMINACA AB-CHMINACA AB-FUBINACA AB-FUBINACA 2-fluorobenzyl isomer AB-PINACA ADB-BINACA ADB-BUTINACA ADB-CHMINACA ADB-HEXINACA ADB-FUBINACA ADB-PINACA ADB-4en-PINACA ADB-5'Br-PINACA ADMB-3TMS-PRINACA Adamantyl-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA CUMYL-3TMS-PRINACA CUMYL-4CN-BINACA CUMYL-CBMINACA CUMYL-CHSINACA CUMYL-EINACA CUMYL-FUBINACA CUMYL-NBMINACA CUMYL-PINACA CUMYL-THPINACA CUMYL-TSINACA EMB-FUBINACA FUB-APINACA MDMB-4en-PINACA MDMB-5Br-INACA MDMB-BINACA MDMB-CHMINACA MDMB-FUBINACA MN-18 PX-2 PX-3 THQ-PINACA Indole-3-carboxamides 4'F-CUMYL-5F-PICA 5F-ADBICA 5F-EDMB-PICA 5F-MDMB-PICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA BMS-F CUMYL-BICA CUMYL-CBMICA CUMYL-CHMICA CUMYL-NBMICA CUMYL-PICA CUMYL-5F-PICA FDU-NNE1 MDMB-CHMICA MMB-CHMICA MMB-2201 MN-25 (UR-12) NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135 Indole-3-carboxylates 5F-PB-22 FDU-PB-22 FUB-PB-22 QUCHIC (BB-22) QUPIC (PB-22) NM-2201 Naphthoylindazoles THJ-018 THJ-2201 Naphthoylindoles 5F-JWH-398 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 JWH-004 JWH-007 JWH-009 JWH-011 JWH-015 JWH-016 JWH-018 JWH-019 JWH-020 JWH-042 JWH-043 JWH-046 JWH-047 JWH-048 JWH-049 JWH-050 JWH-070 JWH-072 JWH-073 JWH-076 JWH-077 JWH-079 JWH-080 JWH-081 JWH-082 JWH-083 JWH-093 JWH-094 JWH-095 JWH-096 JWH-097 JWH-098 JWH-099 JWH-100 JWH-116 JWH-120 JWH-122 JWH-148 JWH-149 JWH-151 JWH-153 JWH-159 JWH-160 JWH-163 JWH-164 JWH-165 JWH-166 JWH-180 JWH-181 JWH-182 JWH-189 JWH-193 JWH-198 JWH-200 JWH-210 JWH-211 JWH-212 JWH-213 JWH-234 JWH-235 JWH-236 JWH-239 JWH-240 JWH-241 JWH-242 JWH-258 JWH-259 JWH-260 JWH-261 JWH-262 JWH-265 JWH-266 JWH-267 JWH-268 JWH-387 JWH-398 JWH-416 JWH-417 JWH-422 JWH-423 JWH-424 JWH-425 MAM-1220 MAM-2201 NE-CHMIMO Naphthoylpyrroles JWH-030 JWH-031 JWH-032 JWH-033 JWH-036 JWH-044 JWH-045 JWH-145 JWH-146 JWH-147 JWH-150 JWH-156 JWH-243 JWH-244 JWH-245 JWH-246 JWH-292 JWH-293 JWH-307 JWH-308 JWH-309 JWH-346 JWH-347 JWH-348 JWH-363 JWH-364 JWH-365 JWH-366 JWH-367 JWH-368 JWH-369 JWH-370 JWH-371 JWH-372 JWH-373 Naphthylmethylindenes JWH-171 JWH-176 JWH-220 Naphthylmethylindoles JWH-175 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199 Phenylacetylindoles Cannabipiperidiethanone JWH-167 JWH-201 JWH-202 JWH-203 JWH-204 JWH-205 JWH-206 JWH-207 JWH-208 JWH-209 JWH-237 JWH-248 JWH-249 JWH-250 JWH-251 JWH-252 JWH-253 JWH-302 JWH-303 JWH-304 JWH-305 JWH-306 JWH-311 JWH-312 JWH-313 JWH-314 JWH-315 JWH-316 RCS-8 Pyrazolecarboxamides 5F-AB-FUPPYCA 5F-AMPPPCA AB-CHFUPYCA Tetramethylcyclo-propanoylindazoles FAB-144 Tetramethylcyclo-propanoylindoles 5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12 Others 2F-QMPSB 4-HTMPIPO 4CN-CUMYL-BUT7AICA 5F-3-pyridinoylindole 5F-ADB-P7AICA 5F-CUMYL-P7AICA 5F-CUMYL-PEGACLONE 5F-PY-PICA 5F-PY-PINACA A-836,339 A-955,840 A-PBITMO A-PONASA AB-001 ADB-FUBHQUCA ADB-FUBIATA ADB-P7AICA AM-1248 AM-1714 Abnormal cannabidiol BAY 38-7271 BAY 59-3074 BzODZ-EPyr CB-13 CB-86 CBS-0550 CUMYL-4CN-B7AICA CUMYL-CB-MEGACLONE CUMYL-CH-MEGACLONE CUMYL-PEGACLONE EG-018 GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-19 MDA-7 MEPIRAPIM NESS-040C5 NMDMSB NMP-7 O-1269 O-1270 O-1399 O-1602 O-2220 O-889 Olorinab PF-03550096 PSB-SB-1202 PTI-1 PTI-2 PTI-3 QMPSB S-444,823 S-777,469 SER-601 Tedalinab URB-447 VSN-16 Vicasinabin WIN 55,212-2 WIN 56,098
Allosteric CBRTooltip Cannabinoid receptor ligands	AEF0117 GAT100 Org 27569 Org 27759 Org 29647 PSNCBAM-1 Pregnenolone RTI-371 ZCZ-011
Endocannabinoidenhancers(inactivation inhibitors)	4-Nonylphenylboronic acid AM-404 Arachidonoyl serotonin ART26.12 Arvanil BIA 10-2474 Biochanin A CAY-10401 CAY-10429 Genistein Guineesine IDFP JNJ 1661010 JNJ-42165279 JZL184 JZL195 Kaempferol LY-2183240 MK-4409 O-1624 O-2093 O-7460 Oleoylethanolamide (OEA) Olvanil Palmitoylethanolamide (PEA) PF-04457845 PF-622 PF-750 PF-3845 PHOP UCM707 URB-447 URB-597 URB-602 URB-754 VDM-11
Anticannabinoids(antagonists/inverseagonists/antibodies)	ABD459 AM-251 AM-281 AM-630 AM-1387 AM-4113 AM-6527 AM-6545 Amauromine ANEB-001 AZD-2207 BML-190 CAY-10508 CB-25 CB-52 CB-86 CE-178253 COR170 Drinabant (AVE1625) Hemopressin Ibipinabant (SLV319) JD-5037 JTE-907 LH-21 LY-320,135 MDA-77 MJ-15 MK-9470 Monlunabant MRL-650 NESS-0327 NIDA-41020 O-606 O-1184 O-1248 O-1918 O-2050 O-2654 Otenabant (CP-945,598) PF-514273 PGN36 PipISB PSB-SB-487 Rezosicone Rimonabant (SR141716) Rosonabant (E-6776) SLV 319 SR-144,528 Surinabant (SR147778) Taranabant (MK-0364) TC-C 14G TM-38837 VCHSR Voacamine Zevaquenabant
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology) List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics