AB-PICA

Last updated
AB-PICA
AB-PICA structure.png
Legal status
Legal status
Identifiers
  • N-[(1S)-1-(aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indole-3-carboxamide
CAS Number
UNII
Chemical and physical data
Formula C19H27N3O2
Molar mass 329.444 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(N)=O)C(C)C)C1=CN(CCCCC)C2=CC=CC=C21
  • InChI=1S/C19H27N3O2/c1-4-5-8-11-22-12-15(14-9-6-7-10-16(14)22)19(24)21-17(13(2)3)18(20)23/h6-7,9-10,12-13,17H,4-5,8,11H2,1-3H3,(H2,20,23)(H,21,24)/t17-/m0/s1
  • Key:GOLDNQQANLFVSP-KRWDZBQOSA-N

AB-PICA is a potent agonist for the CB1 receptor (EC50 = 12 nM) and CB2 receptor (EC50 = 12 nM). [1]

See also

Related Research Articles

<span class="mw-page-title-main">APINACA</span> Chemical compound

APINACA (AKB48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors. It is a full agonist at CB1 with an EC50 of 142 nM and Ki of 3.24 nM (compared to the Ki of Δ9-THC at 28.35 nM and JWH-018 at 9.62 nM), while at CB2 it acts as a partial agonist with an EC50 of 141 nM and Ki of 1.68 nM (compared to the Ki of Δ9-THC at 37.82 nM and JWH-018 at 8.55 nM). Its pharmacological characterization has also been reported in a discontinued patent application. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in March 2012 as an ingredient in synthetic cannabis smoking blends, along with a related compound APICA. Structurally, it closely resembles cannabinoid compounds from a University of Connecticut patent, but with a simple pentyl chain on the indazole 1-position, and APINACA falls within the claims of this patent despite not being disclosed as an example.

<span class="mw-page-title-main">APICA (synthetic cannabinoid drug)</span> Chemical compound

APICA is an indole based drug that acts as a potent agonist for the cannabinoid receptors.

<span class="mw-page-title-main">AB-FUBINACA</span> Chemical compound

AB-FUBINACA (AMB-FUBINACA) is a psychoactive drug that acts as a potent agonist for the cannabinoid receptors, with Ki values of 0.9 nM at CB1 and 23.2 nM at CB2 and EC50 values of 1.8 nM at CB1 and 3.2 nM at CB2. It was originally developed by Pfizer in 2009 as an analgesic medication but was never pursued for human use. In 2012, it was discovered as an ingredient in synthetic cannabinoid blends in Japan, along with a related compound AB-PINACA, which had not previously been reported.

<span class="mw-page-title-main">AB-PINACA</span> Chemical compound

AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.

<span class="mw-page-title-main">ADBICA</span> Group of stereoisomers

ADBICA (also known as ADB-PICA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. ADBICA had not previously been reported in the scientific literature prior to its sale as a component of synthetic cannabis blends. ADBICA features a carboxamide group at the 3-indole position, like SDB-001 and STS-135. The stereochemistry of the tert-butyl side-chain in the product is unresolved, though in a large series of indazole derivatives structurally similar to ADBICA that are disclosed in Pfizer patent WO 2009/106980, activity resides exclusively in the (S) enantiomers. ADBICA is a potent agonist of the CB1 receptor and CB2 receptor with an EC50 value of 0.69 nM and 1.8 nM respectively.

<span class="mw-page-title-main">ADB-FUBINACA</span> Chemical compound

ADB-FUBINACA (ADMB-FUBINACA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.

<span class="mw-page-title-main">ADB-PINACA</span> Chemical compound

ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.52 nM and 0.88 nM respectively. Like MDMB-FUBINACA, this compound contains an amino acid residue of tert-leucine.

<span class="mw-page-title-main">5F-ADB</span> Chemical compound

5F-ADB (also known as MDMB-5F-PINACA 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. 5F-ADB is a potent agonist of the CB1 receptor, 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.

<span class="mw-page-title-main">PX-3</span> Chemical compound

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.

<span class="mw-page-title-main">5F-AB-PINACA</span> Chemical compound

5F-AB-PINACA is an indazole-based synthetic cannabinoid that is derived from a series of compounds originally developed by Pfizer in 2009 as an analgesic medication, and has been sold online as a designer drug.

<span class="mw-page-title-main">5F-APINACA</span> Chemical compound

5F-APINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding pentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.

<span class="mw-page-title-main">MDMB-FUBINACA</span> Chemical compound

MDMB-FUBINACA (also known as MDMB(N)-Bz-F and FUB-MDMB) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with Ki values of 1.14 nM at CB1 and 0.1228 nM at CB2 and EC50 values of 0.2668 nM at CB1 and 0.1411 nM at CB2, and has been sold online as a designer drug. Its benzyl analogue (instead of 4-fluorobenzyl) has been reported to be a potent agonist for the CB1 receptor (Ki = 0.14 nM, EC50 = 2.42 nM). The structure of MDMB-FUBINACA contains the amino acid, 3-methylvaline or tert-leucine methyl ester.

<span class="mw-page-title-main">PX-1</span> Chemical compound

PX-1 is an indole-based synthetic cannabinoid that has been sold online as a designer drug.

<span class="mw-page-title-main">PX-2</span> Chemical compound

PX-2 is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. It contains a phenylalanine amino acid amide as part of its structure.

<span class="mw-page-title-main">APP-FUBINACA</span> Chemical compound

APP-FUBINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Pharmacological testing showed APP-FUBINACA to have only moderate affinity for the CB1 receptor, with a Ki of 708 nM, while its EC50 was not tested. It contains a phenylalanine amino acid residue in its structure.

<span class="mw-page-title-main">5F-ADB-PINACA</span> Chemical compound

5F-ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.24 nM and 2.1 nM respectively.

<span class="mw-page-title-main">AB-FUBICA</span> Chemical compound

AB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 21 nM at CB1 and 15 nM at CB2.

<span class="mw-page-title-main">ADB-FUBICA</span> Chemical compound

ADB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 2.6 nM at CB1 and 3.0 nM at CB2.

<span class="mw-page-title-main">5F-ADBICA</span> Chemical compound

5F-ADBICA (also known as 5F-ADB-PICA) is an indole-based synthetic cannabinoid that is a potent agonist at CB1 receptors and CB2 receptors with EC50 values of 0.77 nM and 1.2 nM respectively.

<span class="mw-page-title-main">FUB-APINACA</span> Chemical compound

FUB-APINACA (also known as A-FUBINACA according to the EMCCDA framework for naming synthetic cannabinoids and FUB-AKB48) is an indazole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is an analog of APINACA and 5F-APINACA where the pentyl chain has been replaced with fluorobenzyl.

References

  1. Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID   26134475.