AM2201   Click here for help

GtoPdb Ligand ID: 9705

Synonyms: AM-2201
Compound class: Synthetic organic
Comment: AM2201 is a highly potent synthetic cannabinoid [2,4]. Both acute and long-term AM2201 intoxication has serious side-effects and can be lethal [3,5]. AM2201 is the terminally fluorinated analogue of JWH-018.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 22
Molecular weight 359.17
XLogP 6.92
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES FCCCCCn1cc(c2c1cccc2)C(=O)c1cccc2c1cccc2
Isomeric SMILES FCCCCCn1cc(c2c1cccc2)C(=O)c1cccc2c1cccc2
InChI InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2
InChI Key ALQFAGFPQCBPED-UHFFFAOYSA-N
References
1. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M et al.. (2015)
Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135.
ACS Chem Neurosci, 6 (8): 1445-58. [PMID:25921407]
2. Hutter M, Moosmann B, Kneisel S, Auwärter V. (2013)
Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism.
J Mass Spectrom, 48 (7): 885-94. [PMID:23832945]
3. Järbe TUC, Raghav JG. (2017)
Tripping with Synthetic Cannabinoids ("Spice"): Anecdotal and Experimental Observations in Animals and Man.
Curr Top Behav Neurosci, 32: 263-281. [PMID:27753006]
4. Makriyannis A, Deng H. (2001)
Cannabimimetic indole derivatives.
Patent number: WO2001028557. Assignee: University Of Connecticut. Priority date: 18/10/1999. Publication date: 26/04/2001.
5. Tournebize J, Gibaja V, Kahn JP. (2017)
Acute effects of synthetic cannabinoids: Update 2015.
Subst Abus, 38 (3): 344-366. [PMID:27715709]