PX-1

Last updated
PX-1
PX-1.svg
Legal status
Legal status
Identifiers
  • (S)-N-(1-amino-1-oxo-3-phenylpropan-2-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C23H26FN3O2
Molar mass 395.478 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(N)=O)CC1=CC=CC=C1)C2=CN(CCCCCF)C3=C2C=CC=C3
  • InChI=1S/C23H26FN3O2/c24-13-7-2-8-14-27-16-19(18-11-5-6-12-21(18)27)23(29)26-20(22(25)28)15-17-9-3-1-4-10-17/h1,3-6,9-12,16,20H,2,7-8,13-15H2,(H2,25,28)(H,26,29)/t20-/m0/s1
  • Key:DDVANTXQCRMRFF-FQEVSTJZSA-N

PX-1 (also known as 5F-APP-PICA and SRF-30) is an indole-based synthetic cannabinoid that has been sold online as a designer drug. [1] [2] [3]

Contents

Legality

Sweden's public health agency suggested classifying PX-1 as hazardous substance on November 10, 2014. [4]

PX-1 is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015. [5]

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, with a Ki of 304.5nM and an EC50 of 585nM at CB1. 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 (WO 2003/035005), 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">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">AB-CHMINACA</span> Chemical compound

AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent. Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.

<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">ADB-CHMINACA</span> Chemical compound

ADB-CHMINACA (also known as MAB-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of Ki = 0.289 nM and was originally developed by Pfizer in 2009 as an analgesic medication. It was identified in cannabinoid blends in Japan in early 2015.

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

5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-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. It was first identified in Japan in early 2014. Although only very little pharmacological information about 5F-AMB itself exists, its 4-cyanobutyl analogue (instead of 5-fluoropentyl) has been reported to be a potent agonist for the CB1 receptor (KI = 0.7 nM).

<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">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-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-PICA</span> Chemical compound

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

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

AMB-FUBINACA (also known as FUB-AMB and MMB-FUBINACA) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with Ki values of 10.04 nM at CB1 and 0.786 nM at CB2 and EC50 values of 0.5433 nM at CB1 and 0.1278 nM at CB2, and has been sold online as a designer drug. It was originally developed by Pfizer which described the compound in a patent in 2009, but was later abandoned and never tested on humans. AMB-FUBINACA was the most common synthetic cannabinoid identified in drug seizures by the Drug Enforcement Administration in 2017 and the first half of 2018.

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

AMB-CHMINACA or MMB-CHMINACA (also known as MA-CHMINACA) is an indazole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug.

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

FUB-APINACA (also known as AFUBINACA 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.

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

MDMB-FUBICA is an indole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug.

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

Adamantyl-THPINACA is an indazole-based synthetic cannabinoid, which was first reported to Europol in Slovenia in January 2015. It is known as both the 1-adamantyl and 2-adamantyl isomers, which can be distinguished by GC-EI-MS. It is banned in Sweden and Russia. Both the 1-adamantyl and 2-adamantyl isomers are specifically listed as illegal drugs in Japan. Given the known metabolic liberation of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of Adamantyl-THPINACA may also release amantadine.

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

5F-EMB-PINACA is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family that has been sold online as a designer drug.

References

  1. "PX 1". Cayman Chemical. Retrieved 15 July 2015.
  2. Presley BC, Logan BK, Jansen-Varnum SA (December 2019). "Phase I metabolism of synthetic cannabinoid receptor agonist PX-1 (5F-APP-PICA) via incubation with human liver microsomes and UHPLC-HRMS". Biomedical Chromatography. 34 (3): e4786. doi:10.1002/bmc.4786. PMID   31863591. S2CID   209435138.
  3. Dahm, Patrick; Thomas, Andreas; Rothschild, Markus A.; Thevis, Mario; Mercer-Chalmers-Bender, Katja (December 2021). "Phase I-metabolism studies of the synthetic cannabinoids PX-1 and PX-2 using three different in vitro models". Forensic Toxicology. 40 (2): 244–262. doi:10.1007/s11419-021-00606-6. ISSN   1860-8973. PMC   9715525 . PMID   36454402. S2CID   245540105.
  4. "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as dangerous to health] (in Swedish). Folkhälsomyndigheten. Retrieved 16 July 2015.
  5. "Misuse of Drugs Act". Singapore Government. 30 April 2015. Retrieved 24 July 2015.