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EAM-2201

Synthetic cannabinoid, CB1 agonist with sub-nanomolar affinity, narcotic in France by generic clause.

Level of detail

C₂₆H₂₆FNO

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.

Data sheet

Names

IUPAC name
(4-ethylnaphthalen-1-yl)-[1-(5-fluoropentyl)indol-3-yl]methanone
Other names
4'-Ethyl-AM-2201 · (4-ETHYLNAPHTHYL)-AM-2201 · 5-fluoro-JWH-210 · JWH-210 N-(5-FLUOROPENTYL)

Identifiers

Formula
C₂₆H₂₆FNO
Molar mass
387.50 g/mol
CAS
1364933-60-7
InChIKey
NSCXPXDWLZORPX-UHFFFAOYSA-N

Class

Family
Synthetic cannabinoid (SCRA)

Legal status

France
Narcotic: generic clause
International
Unscheduled
See the legal framework

Updated on

Receptors and activity

  1. CB1Agonist95 out of 100

    Ki 0,41 ± 0,04 nM (Marusich et coll., 2018) ; CE50 46,8 nM en [35S]GTPγS

  2. CB2Agonist95 out of 100

    Ki 0,38 ± 0,05 nM (Marusich et coll., 2018) ; efficacité maximale de 40,2 % en [35S]GTPγS, contre 55,1 % pour le CP55,940

Bar length shows the relative strength of the interaction, as an indication.

Subjective signature

Calm
5 out of 100
Relaxation of body and mind; reduced mental noise without marked drowsiness.
Clarity
5 out of 100
Sustained attention and clear thinking; functional lucidity, not euphoria.
High
8 out of 100
Euphoria and sensory intensity; altered perception of time and space.
Appetite
8 out of 100
Stimulation of hunger and of taste appreciation (the “munchies” effect).
Sleep
8 out of 100
Sedative effect: aids sleep onset and the continuity of deep sleep.
Editorial estimate, not clinical.

Pharmacology

EAM-2201 is a synthetic cannabinoid of the naphthoylindole family, the 5-fluorinated analogue of JWH-210. In the study by Marusich et al. (2018), its affinity is 0.41 nM at CB1 and 0.38 nM at CB2, and its maximal stimulation of CB1 exceeds that of CP55,940 (270.3% against 163.3% above basal); Costain et al. (2016) rank it among the full CB1 agonists. In mice, it substitutes for THC in a discrimination task with an ED50 of 0.04 µmol/kg, the most potent of the batch tested, although its dose-response curve is not monotonic. Human data are limited to forensic observations: a death from diabetic ketoacidosis in which eleven synthetic cannabinoids, including EAM-2201, were detected in blood (Hess et al., 2015), and a fatal case of intoxication by a mixture combining EAM-2201 with two other synthetic cannabinoids and α-PVP (Yamagishi et al., 2018). No therapeutic use is documented in the sources consulted, and no controlled clinical trial has been published in them.

Key sources.

History

Source
Synthetic molecule: no natural occurrence is reported in the sources consulted. It has been found in illicit products, notably in Japan, where Uchiyama et al. (2013) list it among twelve newly distributed cannabimimetic compounds.

Origin (pharmaceutical research → illicit market)

No biosynthetic pathway is reported: EAM-2201 is not reported from any hemp chemotype or living organism. It belongs to chemical synthesis alone, within the naphthoylindole class.

References

  1. Marusich et coll., Neuropharmacology, 2018 : affinités CB1 et CB2, activation de la [35S]GTPγS et substitution au THC pour l'EAM-2201 (tableau 1) (new tab)PMID 29113898
  2. Costain et coll., Eur J Pharmacol, 2016 : caractérisation pharmacologique des cannabinoïdes de synthèse émergents dans des cellules HEK293T (new tab)PMID 27260125
  3. Cannaert et coll., Analytical Chemistry, 2016 : activité des cannabinoïdes de synthèse et de leurs métabolites dans un test de bioactivité, dont l'EAM-2201 (new tab)PMID 27779402
  4. Kim et coll., J Pharm Biomed Anal, 2016 : métabolisme in vitro de l'EAM-2201 sur microsomes hépatiques humains et CYP recombinants (new tab)PMID 26641707
  5. Kong et coll., Molecules, 2018 : inhibition in vitro des CYP et des UGT par l'EAM-2201 sur microsomes hépatiques humains (new tab)PMID 29659506
  6. Yamagishi et coll., Legal Medicine, 2018 : cas mortel associant EAM-2201, AB-PINACA, AB-FUBINACA et α-PVP, avec dosages sanguins et tissulaires (new tab)PMID 30268690
  7. Hess et coll., Forensic Science International, 2015 : décès par cétoacidose diabétique et cannabinoïdes de synthèse (new tab)PMID 26363623
  8. Uchiyama et coll., Forensic Science International, 2013 : douze cannabimimétiques détectés dans des produits illicites au Japon, dont l'EAM-2201 (new tab)PMID 23063179
  9. Kakehashi et coll., Forensic Science International, 2020 : concentrations sanguines et urinaires de cannabinoïdes de synthèse chez des conducteurs impliqués dans des accidents (new tab)PMID 31902661
  10. ANSM, Liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, famille des indol-3-yl méthanones (new tab)
  11. INCB, Liste verte 2026 des substances sous contrôle international (tableaux de la convention de 1971) (new tab)
  12. PubChem, CID 71308187 (EAM-2201) : formule, masse moléculaire moyenne et InChIKey (new tab)

Structured data

SMILES
CCC1=CC=C(C2=CC=CC=C12)C(=O)C3=CN(C4=CC=CC=C43)CCCCCF
InChIKey
NSCXPXDWLZORPX-UHFFFAOYSA-N

Machine-readable entry (JSON)

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