BMS-F

Chemical compound

BMS-F

Identifiers

IUPAC name

* (S)-2-{[7-Methoxy-2-methyl-1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester

CAS Number|

* 354569-07-6 Y

PubChem CID|

* 10227614

Chemical and physical data
Formula| C27H33N3O5
Molar mass| 479.577 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CC1=C(C2=C(N1CCN3CCOCC3)C(=CC=C2)OC)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)OC

InChI

* InChI=1S/C27H33N3O5/c1-19-24(26(31)28-22(27(32)34-3)18-20-8-5-4-6-9-20)21-10-7-11-23(33-2)25(21)30(19)13-12-29-14-16-35-17-15-29/h4-11,22H,12-18H2,1-3H3,(H,28,31)/t22-/m0/s1

* Key:HQUJODHGYIPBGV-QFIPXVFZSA-N

BMS-F is a chemical from the aminoalkylindole family invented by Bristol-Myers Squibb around 1999,[1] that acts as a potent and selective agonist for the cannabinoid receptor CB2, with a Ki of 8 nM at CB2 and 500x selectivity over the related CB1 receptor. It has antiinflammatory effects and inhibits release of TNF-α.[2][3]

## See also

[edit]

* A-796,260
* APP-FUBINACA
* JWH-200
* MDMB-FUBINACA
* MN-25
* Pravadoline
* S-777,469
* WIN 55,212-2

## References

[edit]

1. ^ WO application 0158869, Leftheris K, Zhao R, Chen BC, Kiener P, Wu H, Pandit CR, Wrobleski S, Chen P, Hynes J, Longphre M, Norris DJ, Spergel S, Tokarski J, "Cannabinoid Receptor Modulators, Their Processes of Preparation, and use of Cannabinoid Receptor Modulators for Treating Respiratory and Non-Respiratory Diseases", published 16 August 2001, assigned to Bristol-Myers Squibb
2. ^ Hynes Jr J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–2402. doi:10.1016/s0960-894x(02)00466-3. PMID 12161142.
3. ^ Howlett AC, Thomas BF, Huffman JW (October 2021). "The Spicy Story of Cannabimimetic Indoles". Molecules. 26 (20): 6190. doi:10.3390/molecules26206190. PMC 8538531. PMID 34684770.

* 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-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|

* 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)

Synthetic
cannabinoid
receptor
agonists /
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
* 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

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
* 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-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-PY-PICA
* 5F-PY-PINACA
* 5F-3-pyridinoylindole
* 5F-ADB-P7AICA
* 5F-CUMYL-P7AICA
* 5F-CUMYL-PEGACLONE
* A-836,339
* A-955,840
* A-PBITMO
* 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
* NMDMSB
* 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 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

Endocannabinoid
enhancers
(inactivation inhibitors)|

* 4-Nonylphenylboronic acid
* AM-404
* Arachidonoyl serotonin
* 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
* Oleoylethanolamide (OEA)
* Olvanil
* Palmitoylethanolamide (PEA)
* PF-04457845
* PF-622
* PF-750
* PF-3845
* PHOP
* URB-447
* URB-597
* URB-602
* URB-754
* VDM-11

Anticannabinoids
(antagonists/inverse
agonists/antibodies)|

* AM-251
* AM-281
* AM-630
* AM-1387
* AM-4113
* AM-6527
* AM-6545
* BML-190
* Brizantin (Бризантин)
* CAY-10508
* CB-25
* CB-52
* CB-86
* Dietressa (Диетресса)
* Drinabant (AVE1625)
* Hemopressin
* Ibipinabant (SLV319)
* JTE-907
* LH-21
* LY-320,135
* MDA-77
* MJ-15
* MK-9470
* NESS-0327
* NIDA-41020
* O-606
* O-1184
* O-1248
* O-1918
* O-2050
* O-2654
* Otenabant (CP-945,598)
* PF-514273
* PipISB
* PSB-SB-487
* Rimonabant (SR141716)
* Rosonabant (E-6776)
* SR-144,528
* Surinabant (SR147778)
* Taranabant (MK-0364)
* TM-38837
* VCHSR

* See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
* List of: AM cannabinoids
* JWH cannabinoids
* Designer drugs § Synthetic cannabimimetics

*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[CBR]: Cannabinoid receptor