PX-3

PX-3
Systematic (IUPAC) name

N-(2-amino-1-benzyl-2-oxo-ethyl)-1-(cyclohexylmethyl)indazole-3-carboxamide
Clinical data
Legal status	CA: Schedule II
Identifiers
CAS Number	1185887-14-2
PubChem	CID 70969676
UNII	3877T06H05^Y
Chemical data
Formula	C₂₄H₂₈N₄O₂
Molar mass	404.5 g/mol
SMILES O=C(N[C@H](C(N)=O)CC1=CC=CC=C1)C2=NN(CC3CCCCC3)C4=C2C=CC=C4
InChI InChI=1S/C24H28N4O2/c25-23(29)20(15-17-9-3-1-4-10-17)26-24(30)22-19-13-7-8-14-21(19)28(27-22)16-18-11-5-2-6-12-18/h1,3-4,7-10,13-14,18,20H,2,5-6,11-12,15-16H2,(H2,25,29)(H,26,30)/t20-/m0/s1 Key:DMHWDSGURMXMGE-FQEVSTJZSA-N

PX-3 (also known as APP-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB₁ receptor with a binding affinity of Ki = 47.6 nM and was originally developed by Pfizer in 2009 as an analgesic medication.^[1]^[2]^[3]

The acronym 'APP' signifies the 'amino', 'phenyl' and 'propanone' elements of the structure. Three related compounds, PX-1 (5F-APP-PICA, SRF-30), PX-2 (5F-APP-PINACA, FU-PX) and APP-FUBINACA were reported by the EMCDDA in late 2014.^[4]^[5]

Legality

Sweden's public health agency suggested to classify APP-CHMINACA as hazardous substance on June 1, 2015.^[6]

References

↑ "APP-CHMINACA". Cayman Chemical. Retrieved 24 June 2015.
↑ "Patent WO/2009/106980 - Indazole derivatives".
↑ "EWS Forum - In Belgien wurde die neue psychoaktive Substanz N-(2-amino-1-benzyl-2-oxo-ethyl)-1-(cyclohexylmethyl)indazole-3-carboxamide (APP-CHMINACA) identifiziert.". Retrieved 24 June 2015.
↑ "EWS Forum - In Schweden wurde die neue psychoaktive Substanz N-(1-amino-1-oxo-3-phenylpropan-2-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (5F-APP-PICA) identifiziert.". Retrieved 24 June 2015.
↑ "EWS Forum - In Schweden wurden folgende drei neue psychoaktive Substanzen identifiziert.". Retrieved 24 June 2015.
↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten. Retrieved 29 June 2015.

Cannabinoids

Phytocannabinoids

Active metabolites: 8,11-DiOH-THC
11-COOH-THC
11-OH-THC

Endocannabinoids

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 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-910 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1871 SPA-229 Tinabinol 2-Isopropyl-5-methyl-1- (2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

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

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-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-2201 NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135 UR-12 (MN-25)

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	5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-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-PINACA CUMYL-THPINACA EMB-FUBINACA FUB-APINACA 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 AB-CHMFUPPYCA

Others	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 BAY 38-7271 BAY 59-3074 BIM-018 CB-13 CB-86 CBS-0550 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 PF-03550096 PSB-SB-1202 PTI-1 PTI-2 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)

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: Cannabinoidergics (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics

Cannabinoidergics

Receptor
(ligands)

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 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 Magnolol MDA-19 Nabitan NADA 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

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

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: Cannabinoids (cannabinoids by structure)

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PX-3

Legality

See also

References