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Synthetic

(+/-)-AM-2233

A synthetic cannabinoid, a full CB1 agonist: a laboratory tracer diverted into a smoking product.

Narcotic: named in schedule
Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

C₂₂H₂₃IN₂O

CAS 444912-75-8

Family
Synthetic CB receptor agonistNew psychoactive substance
Molar mass
458.30 g/mol

Updated on

In plain terms

AM-2233 is a synthetic cannabinoid, made in a laboratory and with no connection to the hemp plant. It was designed as a brain imaging tool in animals, before being found in illegal smoking products sold as cannabis substitutes. It binds to the same receptors as THC with a very high affinity, and no human data make it possible to describe its real effects or risks.

Receptors and activity

Target network

CB1AgonistKi = 6.6 nM · human[3H]CP55,940 displacement, membranes of HEK-293 cells expressing hCB1
  • Activates
  • Binds or modulates

The lower the cited value, the closer the target sits to (+/-)-AM-2233: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of (+/-)-AM-2233.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1AgonistKi = 6.6 nM · human70 out of 100

    Marusich et al. 2018, Neuropharmacology (new tab) · [3H]CP55,940 displacement, membranes of HEK-293 cells expressing hCB1

  2. CB2Binding (function not established)Ki = 0.5 nM · human89 out of 100

    Marusich et al. 2018, Neuropharmacology (new tab) · [3H]CP55,940 displacement, membranes of HEK-293 cells expressing hCB2

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

AM-2233 belongs to the aminoalkylindoles: an indole nucleus bearing a 2-iodobenzoyl group and a (1-methylpiperidin-2-yl)methyl chain. It binds with high affinity to the CB1 receptor, with an inhibition constant of 6.63 nM at the human receptor and 0.2 nM on mouse hippocampal membranes, most of this affinity residing in the (R) enantiomer. The decisive difference from THC lies in efficacy: THC is only a partial agonist of CB1, whereas AM-2233 behaves as a full agonist in a signalling assay. In rodents, it reproduces the discriminative effects of THC with about twice the potency, and this substitution is reversed by rimonabant, confirming mediation by CB1. At CB2 the picture is different: affinity is very high, at 0.48 nM, but the molecule hardly activates the G protein (efficacy of 21 %). No activity is documented at TRPV1, GPR55, PPARγ or 5-HT1A, no metabolism study was found, and human data are entirely lacking.

Key sources.

History

Source
An entirely synthetic molecule, absent from hemp as from any living organism. It comes from medicinal chemistry work at the Center for Drug Discovery of Northeastern University in Boston, which sought cannabinergic ligands easy to label with radioactive iodine for brain imaging (Deng 2005). It was later identified as a component of illegal products in Japan (Uchiyama 2012), where azepane isomers of AM-2233 were also analysed in designer drugs (Nakajima 2013), and it is among the most potent compounds recently found in the United States (Marusich 2018).

Origin

Laboratory synthesis

No biological pathway: the molecule is produced by no living organism and results from no enzymatic reaction. It is obtained by chemical synthesis, described here only by its chemical class, the aminoalkylindoles.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › New psychoactive substance

Class

aminoalkylindole

Verification

Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.

Wikipedia (English)

AM-2233 (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Deng et al., Journal of Medicinal Chemistry, 2005: potent radioiodinatable cannabinergic indole analogues for brain imaging of the CB1 receptor (AM2233) (new tab)PMID 16190764
  2. Marusich et al., Neuropharmacology, 2018: characterisation of eight synthetic agonists including AM-2233 (binding and activation of hCB1 and hCB2, THC discrimination) (new tab)PMID 29113898
  3. Shen et al., European Journal of Pharmacology, 2006: the F200A mutation of the human CB1 receptor converts AM2233 from an agonist into an inverse agonist (EC50 of 0.93 nM at the wild-type receptor) (new tab)PMID 16438957
  4. Luk et al., British Journal of Pharmacology, 2004: a potent, highly efficacious, slowly desensitising CB1 agonist; AM2233 is a full agonist there (new tab)PMID 15148260
  5. Dhawan et al., Synapse, 2006: in vivo receptor occupancy with R-[125/131I]AM2233 in the mouse (new tab)PMID 16715483
  6. Järbe et al., Behavioural Pharmacology, 2011: cannabinergic aminoalkylindoles (AM678=JWH018, AM2233…) in THC discrimination in the rat (new tab)PMID 21836461
  7. Uchiyama et al., Forensic Toxicology, 2012: identification of two novel-type synthetic cannabinoids (APICA, APINACA) and detection of five synthetic cannabinoids, including AM-2233, in illegal products (new tab)DOI 10.1007/s11419-012-0136-7
  8. Nakajima et al., Forensic Toxicology, 2013: analysis of the azepane isomers of AM-2233 and AM-1220 obtained as designer drugs in the Tokyo area (new tab)DOI 10.1007/s11419-012-0169-y
  9. Berg et al., Drug Testing and Analysis, 2016: urinary determination of synthetic cannabinoids and metabolites including AM-2233 by UHPSFC-MS/MS and UHPLC-MS/MS (new tab)PMID 26304456
  10. Williams et al., Journal of Analytical Toxicology, 2019: validated method for detecting 19 synthetic cannabinoids, including AM-2233, in oral fluid (new tab)PMID 30060217
  11. ANSM, consolidated list of substances classified as narcotics, updated 16 February 2026, annex IV: AM-2233 (indol-3-yl methanone family) (new tab)
  12. INCB, Green List of psychotropic substances under international control, 35th edition, 2024 (Schedule II: AM-2233 absent) (new tab)
  13. PubChem, Compound Summary CID 10226340, AM-2233 (new tab)

Identifiers

Names

IUPAC name
(2-iodophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone
Other names
AM-2233 · AM2233 · (±)-AM-2233

Identifiers

Formula
C₂₂H₂₃IN₂O
CAS
444912-75-8
PubChem CID
10226340(new tab)
InChIKey
KSLCYQTUSSEGPT-UHFFFAOYSA-N
SMILES
CN1CCCCC1CN2C=C(C3=CC=CC=C32)C(=O)C4=CC=CC=C4I

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.