Synthetic cannabinoid (SCRA)
Narcotic: named in scheduleAM-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
- CB1Ki ≈ 1,0 nMAgonist
- CB2Ki ≈ 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.
- Calm30
- Clarity20
- Sleep50
- Appetite55
- High95
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).
Key sources.
Origin (pharmaceutical research → illicit market)
5-fluoropentyl analogue of JWH-018 - synthesised to increase brain penetration and CB1 potency
Legal framework
International
Non listé
European Union
Décision Conseil 2014/688/UE
France
Annexe IV : listé
Arrêté 27 juil 2012, NOR AFSP1230815A
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Synthetic cannabinoid (SCRA)
- Origin
- Pharmaceutical research (Makriyannis, UMass)
- Status
- Narcotic: named in schedule
References
- 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
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.