Arachidonyl trifluoromethyl ketone

Names
Preferred IUPAC name

(6Z,9Z,12Z,15Z)-1,1,1-Trifluorohenicosa-6,9,12,15-teraen-2-one

Other names

* Arachidonic acid trifluoromethyl ketone
* Arachidonyltrifluoromethane
* Arach-CF3
* AACOCF3

Identifiers

CAS Number

* 149301-79-1

3D model (JSmol)

* Interactive image

ChemSpider |

* 4444095

PubChem CID

* 5280436

UNII |

* 00XIW1CR0F Y

InChI

* InChI=1S/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-

Key: PLWROONZUDKYKG-DOFZRALJSA-N

SMILES

* CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F

Properties

Chemical formula

| C21H31F3O
Molar mass | 356.473 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Arachidonyl trifluoromethyl ketone (ATK) is an analog of arachidonic acid.[1] that inhibits some isoforms of the enzyme phospholipase A2.[2] Specifically it inhibits the 85 kDa cystolic PLA2 (cPLA2).[2]

It has been studied as a neuroprotective agent after spinal cord injury,[2][3] and in animal models of multiple sclerosis.[4]

## See also

* Spinal stenosis

## References

1. ↑ Street, Ian P.; Lin, Hung Kuei; Laliberte, France; Ghomashchi, Farideh; Wang, Zhaoyin; Perrier, Helene; Tremblay, Nathalie M.; Huang, Zheng et al. (1993). "Slow- and tight-binding inhibitors of the 85-k Da human phospholipase A2". Biochemistry 32 (23): 5935–5940. doi:10.1021/bi00074a003. PMID 8018213.
2. ↑ 2.0 2.1 2.2 Khan, Mushfiquddin; Shunmugavel, Anandakumar; Dhammu, Tajinder S; Matsuda, Fumiyo; Singh, Avtar K; Singh, Inderjit (2015). "Oral administration of cytosolic PLA2 inhibitor arachidonyl trifluoromethyl ketone ameliorates cauda equina compression injury in rats". Journal of Neuroinflammation 12. doi:10.1186/s12974-015-0311-y. PMID 25971887.
3. ↑ Huang, Wenlong; Bhavsar, Amar; Ward, Rachael E; Hall, Jodie C.E.; Priestley, John V.; Michael-Titus, Adina T. (2009). "Arachidonyl trifluoromethyl ketone is neuroprotective after spinal cord injury". Journal of Neurotrauma 26 (8): 1429–1434. doi:10.1089/neu.2008-0835. PMID 19371144.
4. ↑ Vana, Adam C.; Li, Shihe; Ribeiro, Rachel; Tchantchou, Flaubert; Zhang, Yumin (2011). "Arachidonyl trifluoromethyl ketone ameliorates experimental autoimmune encephalomyelitis via blocking peroxynitrite formation in mouse spinal cord white matter". Experimental Neurology 231 (1): 45–55. doi:10.1016/j.expneurol.2011.05.014. PMID 21683698. http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1042&context=usuhs.

* v
* t
* e

Cannabinoids

Phytocannabinoids|

* Alkylamides
* Caryophyllene
* CBC
* CBCV
* CBD
* CBDV
* CBG
* CBGM
* CBGV
* CBL
* CBDL
* CBN
* CBV
* Epigallocatechin gallate
* Gallocatechol
* Perrottetinene
* Serinolamide A
* THC
* THC-C4
* THCA
* THCV
* Yangonin

* Active metabolites: 8,11-DiOH-THC
* 11-COOH-THC
* 11-OH-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
cannabinoids|

| Classical cannabinoids
(dibenzopyrans)|

* 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
* AMG-1
* AMG-3
* AMG-36
* AMG-41
* Dexanabinol (HU-211)
* DMHP
* Dronabinol
* HHC
* HU-210
* HU-243
* JWH-051
* JWH-133
* JWH-139
* JWH-161
* JWH-229
* JWH-359
* 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
* THC-O-acetate
* THC-O-phosphate

|

Non-classical
cannabinoids|

* Cannabicyclohexanol
* CBD-DMH
* CP 47,497
* (C6)-CP 47,497
* (C9)-CP 47,497
* CP 55,244
* CP 55,940
* HU-308
* 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
* SPA-229
* Tinabinol

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

Naphthoylindoles|

* AM-1220
* AM-1221
* AM-1235
* AM-2201
* AM-2232
* CHM-081
* EAM-2201
* FUB-JWH-018
* JWH-007
* JWH-015
* JWH-018
* JWH-019
* JWH-073
* JWH-081
* JWH-098
* JWH-116
* JWH-122
* JWH-149
* JWH-164
* JWH-182
* JWH-193
* JWH-198
* JWH-200
* JWH-210
* JWH-398
* JWH-424
* MAM-1220
* MAM-2201
* NE-CHMIMO

Naphthoylindazoles|

* THJ-018
* THJ-2201

Pyrrolobenzoxazines|

* WIN 55,212-2

Naphthylmethylindoles|

* JWH-175
* JWH-176
* JWH-184
* JWH-185
* JWH-192
* JWH-194
* JWH-195
* JWH-196
* JWH-197
* JWH-199

Phenylacetylindoles|

* Cannabipiperidiethanone
* JWH-167
* JWH-203
* JWH-249
* JWH-250
* JWH-251
* JWH-302
* RCS-8

Indole-3-carboxamides|

* 5F-ADBICA
* 5F-MDMB-PICA
* 5F-NNE1
* 5F-PCN
* 5F-SDB-006
* AB-FUBICA
* AB-PICA
* ADBICA
* ADB-FUBICA
* APICA
* CUMYL-BICA
* 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

Tetramethylcyclo-
propanoylindoles|

* 5Br-UR-144
* 5Cl-UR-144
* A-796,260
* A-834,735
* FUB-144
* UR-144
* XLR-11
* XLR-12

Indazole-3-
carboxamides|

* 4F-MDMB-BINACA
* 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-CHMINACA
* ADB-FUBINACA
* ADB-PINACA
* Adamantyl-THPINACA
* ADSB-FUB-187
* AMB-CHMINACA
* AMB-FUBINACA
* APINACA (AKB48)
* APP-FUBINACA
* CUMYL-4CN-BINACA
* CUMYL-PINACA
* CUMYL-THPINACA
* EMB-FUBINACA
* FUB-APINACA
* MDMB-4en-PINACA
* MDMB-FUBINACA
* MDMB-CHMINACA
* MN-18
* PX-2
* PX-3

Tetramethylcyclo-
propanoylindazoles|

* FAB-144

Naphthoylpyrroles|

* JWH-030
* JWH-147
* JWH-307
* JWH-369
* JWH-370

Eicosanoids|

* AM-883
* AM-1346
* ACEA
* ACPA
* Methanandamide (AM-356)
* O-585
* O-689
* O-1812
* O-1860
* O-1861

Pyrazolecarboxamides|

* 5F-AB-FUPPYCA
* AB-CHFUPYCA

Others|

* 2F-QMPSB
* 4-HTMPIPO
* 5F-PY-PICA
* 5F-PY-PINACA
* 5F-3-pyridinoylindole
* A-836,339
* A-955,840
* Abnormal cannabidiol
* AB-001
* BzODZ-EPyr
* AM-1248
* AM-1714
* AZ-11713908
* AZD-1940
* BAY 38-7271
* BAY 59-3074
* BIM-018
* CB-13
* CB-86
* CBS-0550
* CUMYL-4CN-B7AICA
* 5F-CUMYL-P7AICA
* CUMYL-PEGACLONE
* FUBIMINA
* 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
* SER-601
* Tedalinab
* URB-447
* VSN-16
* WIN 56,098

Allosteric CBR ligands|

* Org 27569
* Org 27759
* Org 29647
* RTI-371
* Pregnenolone

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

* v
* t
* e

Cannabinoid receptor modulators

Receptor
(ligands)</small>|

| CB1|

* Agonists (abridged; see here for more): 2-AG
* 2-AGE (noladin ether)
* 11-Hydroxy-THC
* α-Amyrin · β-Amyrin
* AB-CHMINACA
* AM-1172
* AM-1220
* AM-1221
* AM-1235
* AM-2201
* AM-2232
* Anandamide
* Arvanil
* 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

* Antagonists: AM-251
* AM-6545
* Cannabidiol
* Cannabigerol
* Drinabant
* Falcarinol (carotatoxin)
* Hemopressin
* Ibipinabant
* LY-320,135
* MK-9470
* NESS-0327
* O-2050
* Otenabant
* PF-514273
* PipISB
* Rimonabant
* Rosonabant
* Surinabant
* Taranabant
* THCV
* TM-38837
* VCHSR
* Virodhamine

* Antibodies: Brizantin (Бризантин)
* Dietressa (Диетресса)

* Unknown/unsorted: MAFP

|

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-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: 4-O-Methylhonokiol
* AM-630
* BML-190
* Cannabidiol
* Honokiol
* JTE-907
* SR-144,528
* WIN 54,461
* WIN 56,098

NAGly
(GPR18)|

* Agonists: Abnormal cannabidiol
* ACPA
* AM251
* Anandamide
* Cannabidiol
* NADGly
* THC (dronabinol)
* O-1602

* Antagonists: CID-85469571
* O-1918

GPR55|

* Agonists: 2-AGE (noladin ether)
* 2-ALPI
* Abnormal cannabidiol
* AM-251
* CID1011163
* CID1252842
* CID1792579
* CP 55,940
* GSK-494581A
* Lysophosphatidylinositol
* ML-184
* ML-185
* ML-186
* O-1602
* Oleoylethanolamide
* Palmitoylethanolamide
* THC (dronabinol)

* Antagonists: Cannabidiol
* CID-16020046
* ML-191
* ML-192
* ML-193
* O-1918
* PSB-SB-487
* PSB-SB-1202
* PSB-SB-1203
* Tetrahydromagnolol

GPR119|

* Agonists: 2-Oleoylglycerol
* Anandamide
* APD668
* AR-231,453
* AS-1269574
* MBX-2982
* N-Oleoyldopamine
* Oleoylethanolamide
* Olvanil
* PSN-375,963
* PSN-632,408

Unsorted|

* Agonists: Revosimeline

Transporter
(modulators)|

| eCBTs|

* Inhibitors: 5'-DMH-CBD
* AM-404
* AM-1172
* Arachidonoyl serotonin
* Arvanil
* Cannabidiol
* Guineensine
* LY-2183240
* O-2093
* OMDM-2
* Paracetamol (acetaminophen)
* SB-FI-26
* UCM-707
* URB-597
* VDM-11
* WOBE490
* WOBE491
* WOBE492

|

Enzyme
(modulators)|

| FAAH|

* Inhibitors: 4-Nonylphenylboronic acid
* AACOCF3
* AM-404
* Arachidonoyl serotonin
* BIA 10-2474
* Biochanin A
* Genistein
* IDFP
* JNJ-1661010
* JNJ-42165279
* JZL-195
* Kaempferol
* LY-2183240
* MAFP
* Palmitoylisopropylamide
* Paracetamol (acetaminophen)
* PF-3845
* PF-04457845
* PF-750
* SA-47
* SA-57
* TAK 21d
* TC-F 2
* UCM710
* URB-597

* Activators: PDP-EA

|

MAGL|

* Inhibitors: ABX-1431
* IDFP
* JJKK 048
* JW 642
* JZL-184
* JZL-195
* JZP-361
* KML 29
* MAFP
* MJN110
* NAM
* Pristimerin
* URB-602

ABHD6|

* Inhibitors: JZP-169
* JZP-430
* KT182
* KT185
* KT195
* KT203
* LEI-106
* ML294
* ML295
* ML296
* UCM710
* WWL-70

ABHD12|

* Inhibitors: Betulinic acid
* Maslinic acid
* MAFP
* Oleanolic acid
* Orlistat (tetrahydrolipstatin)
* Ursolic acid

Others|

* Precursors: Phosphatidylethanolamine
* NAPE
* Diacylglycerol

* Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
* ARN-272 (FAAH-like anandamide transporter inhibitor)

See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Arachidonyl trifluoromethyl ketone. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Arachidonyl_trifluoromethyl_ketone&oldid=4176835"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[CBR]: Cannabinoid receptor
*[CB1]: Cannabinoid receptor type 1
*[CB2]: Cannabinoid receptor type 2
*[NAGly]: N-Arachidonyl glycine receptor
*[GPR18]: G protein-coupled receptor 18
*[GPR55]: G protein-coupled receptor 55
*[GPR119]: G protein-coupled receptor 119
*[eCBTs]: Endocannabinoid transporter
*[FAAH]: Fatty acid amide hydrolase
*[ABHD6]: alpha/beta-Hydrolase domain containing 6
*[ABHD12]: alpha/beta-Hydrolase domain containing 12