AM-694

Chemical compound

AU: S9 (Prohibited substance)
CA: Schedule II
DE: Anlage II (Authorized trade only, not prescriptible)
UK: Class B
US: Schedule I

Identifiers

IUPAC name

1-[(5-Fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone

CAS Number

335161-03-0^N

PubChem CID

9889172

ChemSpider

8064843^Y

UNII

6RK7KN7L1O

ChEBI

CHEBI:138017

CompTox Dashboard (EPA)

DTXSID30187156

Chemical and physical dataFormulaC₂₀H₁₉FINOMolar mass435.281 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

Ic2ccccc2C(=O)c1cn(CCCCCF)c3ccccc13

InChI

InChI=1S/C20H19FINO/c21-12-6-1-7-13-23-14-17(15-8-3-5-11-19(15)23)20(24)16-9-2-4-10-18(16)22/h2-5,8-11,14H,1,6-7,12-13H2^Y
Key:LFFIIZFINPPEMC-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer drug that acts as a potent and selective agonist for the cannabinoid receptor CB₁. It is used in scientific research for mapping the distribution of CB₁ receptors.^[1]

Pharmacology

AM-694 is an agonist for cannabinoid receptors. It has a K_i of 0.08 nM at CB₁ and 18 times selectivity over CB₂ with a K_i of 1.44 nM.^[2] It is unclear what is responsible for this unusually high CB₁ binding affinity, but it makes the ¹⁸F radiolabelled derivative of AM-694 useful for mapping the distribution of CB₁ receptors in the body.^[1]

Metabolism

Pathways of metabolism include hydrolytic defluorination, carboxylation, and monohydroxylation of the N-alkyl chain.^[3]^[4]

References

^ ^a ^b Willis PG, Katoch-Rouse R, Horti AG (August 2003). "Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand". Journal of Labelled Compounds and Radiopharmaceuticals. 46 (9): 799–804. doi:10.1002/jlcr.720.
^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^ Grigoryev A, Kavanagh P, Melnik A (February 2013). "The detection of the urinary metabolites of 1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone (AM-694), a high affinity cannabimimetic, by gas chromatography - mass spectrometry". Drug Testing and Analysis. 5 (2): 110–5. doi:10.1002/dta.1336. PMID 22522907.
^ Apirakkan O, Gavrilović I, Cowan DA, Abbate V (July 2020). "In Vitro Phase I Metabolic Profiling of the Synthetic Cannabinoids AM-694, 5F-NNEI, FUB-APINACA, MFUBINAC, and AMB-FUBINACA". Chemical Research in Toxicology. 33 (7): 1653–1664. doi:10.1021/acs.chemrestox.9b00466. PMID 32301604. S2CID 215803607.

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-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
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

Synthetic
cannabinoid
receptor
agonists /
neocannabinoids

Classical cannabinoids (dibenzopyrans)	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 CP 42,096 Delta-3-THC Delta-4-THC Delta-7-THC Delta-10-THC Dexanabinol (HU-211) DMHP Dronabinol HU-210 HU-243 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
Non-classical cannabinoids	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
Hydrocarbons	JWH-171 JWH-176 JWH-220
Indazole carboxamides	AB-PINACA AB-FUBINACA
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 AB-CHMINACA AB-FUBINACA AB-FUBINACA 2-fluorobenzyl isomer AB-PINACA ADB-BINACA ADB-CHMINACA ADB-HEXINACA ADB-FUBINACA ADB-PINACA ADB-4en-PINACA ADB-5'Br-PINACA Adamantyl-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA CUMYL-4CN-BINACA CUMYL-CBMINACA CUMYL-CHSINACA CUMYL-FUBINACA CUMYL-NBMINACA CUMYL-PINACA CUMYL-THPINACA CUMYL-TSINACA EMB-FUBINACA FUB-APINACA MDMB-4en-PINACA MDMB-5Br-INACA MDMB-FUBINACA MDMB-CHMINACA 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
Pyrrolobenzoxazines	WIN 55,212-2
Quinolinyl esters	PB-22 5F-PB-22
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
Tetramethylcyclo- propylindoles	UR-144 XLR-11
Others	2F-QMPSB 4-HTMPIPO 4CN-CUMYL-BUT7AICA 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole 5F-ADB-P7AICA 5F-CUMYL-P7AICA 5F-CUMYL-PEGACLONE A-836,339 A-955,840 A-PONASA Abnormal cannabidiol AB-001 ADB-FUBHQUCA ADB-FUBIATA ADB-P7AICA AM-1248 AM-1714 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-7 MDA-19 MEPIRAPIM NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 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 WIN 56,098