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Canna·wikiAM-2201

Synthetic cannabinoid (SCRA)

Narcotic: named in schedule

AM-2201AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole)

[1-(5-fluoropentyl)-1H-indol-3-yl](naphthalen-1-yl)methanone

Aliases.1-(5-fluoropentyl)-3-(1-naphthoyl)indole

Fluorinated analogue of JWH-018, ≈ 9× more potent. Second wave of the Spice market (2010-2012).

Updated on

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.

Identifiers

Formula
C₂₄H₂₂FNO
Molar mass
359.44 g·mol⁻¹
CAS
335161-24-5
PubChem CID
53393997
First described
2001
Origin
Pharmaceutical research (Makriyannis, UMass)
InChIKey
ALQFAGFPQCBPED-UHFFFAOYSA-N

In plain terms

AM-2201 is an "improved" version of JWH-018 - more potent still and more dangerous. Present in second-generation "Spice" mixtures.

Receptors and activity

  • CB1
    Ki ≈ 1,0 nMAgonist
  • CB2
    Ki ≈ 2,6 nMAgonist
  • Agonist
  • Partial agonist
  • Antagonist
  • Modulator
  • Inverse agonist

Hover over a row for the precise value (Ki, EC50…)

Subjective signature

Hover over an axis to read its definition.

  • Calm
    30
  • Clarity
    20
  • Sleep
    50
  • Appetite
    55
  • High
    95

Editorial estimate, not clinical.

Pharmacology

AM-2201 is the fluorinated (5-fluoropentyl) analogue of JWH-018, synthesised within the SAR programme of the Alexandros Makriyannis group (UMass, 2000s). The terminal fluorine increases lipophilicity and brain penetration: in vivo it is ≈ 9× more potent than JWH-018 (Wiley et al. 2014). It appeared on the illicit European market in 2010-2012 as a replacement for the controlled JWH-018. Severe convulsions and tachycardia are documented (Schneir and Baumbacher 2012, PMID 22463729). Listed in Annex IV in France by the **Decree of 27 July 2012** (NOR AFSP1230815A).

Origin (pharmaceutical research → illicit market)

5-fluoropentyl analogue of JWH-018 - synthesised to increase brain penetration and CB1 potency

Structural classification

Class
Synthetic cannabinoid (SCRA)
Origin
Pharmaceutical research (Makriyannis, UMass)
Status
Narcotic: named in schedule

References

  1. 1.Schneir · Ann Emerg Med 2012PMID 22463729

Structured data

InChIKey
ALQFAGFPQCBPED-UHFFFAOYSA-N
SMILES
C1=CC=C2C(=C1)C=CC=C2C(=O)C3=CN(C4=CC=CC=C43)CCCCCF
Formula
C24H22FNO
Molar mass
359.44 g·mol⁻¹
CAS
335161-24-5
PubChem CID
53393997
Machine-readable entry (JSON)

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