AM-694
A synthetic cannabinoid agonist diverted from laboratory use, with no link to hemp.
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.
C₂₀H₁₉FINO
CAS 335161-03-0
- Family
- Synthetic CB receptor agonistResearch ligand or medicine
- Molar mass
- 435.30 g/mol
Updated on
In plain terms
AM-694 is a laboratory molecule, with no link whatsoever to hemp. Created to serve as a radioactive tracer in brain research, it was later found in products in Ireland in 2010. It is not a consumer product: it acts on the same receptors as cannabis, with an affinity that varies greatly between assays.
Receptors and activity
Target network
- Activates
The lower the cited value, the closer the target sits to AM-694: 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-694.
CB1CB1 found in 7 regions of the body
- Basal gangliadenseMost dense in basal ganglia outflow nuclei1
- CerebellumdenseVery dense in the cerebellum1
- HippocampusdenseVery high concentrations in the hippocampus2
- AmygdaladenseHigh concentrations in the amygdala2
- CortexpresentPresent throughout the neocortex2
- Adipose tissuepresentExpressed in adipose tissue3
- GutpresentColonic epithelium, smooth muscle and plexus4
Map sources
- Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
- 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)
- Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
- Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)
Cited values
- CB1AgonistKi = 281 nM43 out of 100
Lee et al. 2020, Molecules (new tab) · competition with [3H]SR141716A (antagonist radioligand), ChemiScreen CB1 membrane preparation; pKi 6.553
- CB2Agonistno measured value cited
CB2 Ki between 1 and 10 nM according to the review by Debruyne and Le Boisselier (2015)
Pharmacology
AM-694 belongs to the benzoylindoles, one of the families of synthetic cannabinoid agonists. It was designed as an imaging probe for the CB1 receptor: the iodine in the ortho position makes it radiolabellable and the 5-fluoropentyl chain permits labelling with fluorine 18. The published affinities place it among the most potent CB1 ligands of its series, but they are taken from the primary literature, and an independent measurement carried out with an antagonist radioligand gives a far lower value (pKi 6.553, Ki of about 281 nM): the exact order of magnitude remains debated. For AM-694 precisely, no published measurement of functional efficacy has been found and controlled human data are lacking: the literature documents only clinical and forensic cases.
Key sources.
- Grigoryev A, Kavanagh P, Melnik A. GC-MS detection of the urinary metabolites of AM-694, Drug Testing and Analysis, 2013 (new tab)PMID 22522907
- Bertol E, Vaiano F, Di Milia MG, Mari F. In vivo detection of AM-694 and its metabolites, Forensic Science International, 2015 (new tab)PMID 26295909
- Hutter M et al. Major in vivo metabolites of nine synthetic cannabinoid agonists including AM-694, Current Pharmaceutical Biotechnology, 2018 (new tab)PMID 29745330
- Apirakkan O, Gavrilović I, Cowan DA, Abbate V. In vitro phase I metabolic profile of AM-694, Chemical Research in Toxicology, 2020 (new tab)PMID 32301604
- Debruyne D, Le Boisselier R. Emerging drugs of abuse: current perspectives on synthetic cannabinoids, Substance Abuse and Rehabilitation, 2015 (table of CB1 and CB2 affinities) (new tab)PMID 26543389
- Lee W et al., Molecules, 2020: QSAR of the CB1 affinity of synthetic cannabinoids; measured pKi of AM-694: 6.553 (competition with [3H]SR141716A, ChemiScreen CB1 membranes) (new tab)PMID 33371501
- de Oliveira MC et al. Toxicity of Synthetic Cannabinoids in K2/Spice: A Systematic Review, Brain Sciences, 2023 (new tab)PMID 37508922
- Giorgetti A, Busardò FP, Tittarelli R, Auwärter V, Giorgetti R. Post-mortem toxicology of synthetic cannabinoid agonists, Frontiers in Psychiatry, 2020 (new tab)PMID 32523555
- Makriyannis A, Deng H. Cannabimimetic indole derivatives, patent WO 01/28557, University of Connecticut, 2001 (new tab)
- Willis PG, Katoch-Rouse R, Horti AG. Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand. J Labelled Comp Radiopharm, 2003 (new tab)DOI 10.1002/jlcr.720
- Order of 19 May 2015 amending the order of 22 February 1990 setting the list of substances classified as narcotics (Légifrance) (new tab)
- ANSM, consolidated list of substances classified as narcotics (Annex IV) (new tab)
- Consolidated Framework Decision 2004/757/JHA, annex of substances subject to control in the Union (EUR-Lex) (new tab)
- INCB, Green List of psychotropic substances under international control (new tab)
History
- Source
- An entirely synthetic molecule, absent from hemp and from any other plant. It comes from academic medicinal chemistry (a patent from Makriyannis's team, published in 2001), then was reported in products in Ireland in 2010 (Grigoryev et al., 2013).
Origin
Laboratory synthesis
No biological pathway: AM-694 has no plant or enzymatic precursor. It is obtained by chemical synthesis, with no equivalent whatsoever in hemp.
Legal framework
- European Union
No control measure at Union level. AM-694 does not appear in the annex to Framework Decision 2004/757/JHA, which lists the substances subject to control throughout the Union, unlike synthetic cannabinoids such as MDMB-CHMICA or CUMYL-4CN-BINACA. It is, however, monitored by the European early warning system since it was reported by Ireland in 2010, and France classifies it at national level. At international level, it is absent from the INCB Green List: it is listed in no schedule of the 1971 Convention, whereas its relatives AM-2201 and JWH-018 do appear there.
- France
Classified as a narcotic in France, and named explicitly. The decree of 19 May 2015, amending the decree of 22 February 1990, entered into annex IV « AM-694 or 1-(5-fluoropentyl)-3-(2-iodobenzoyl) indole »; the ANSM consolidated list reproduces it. The generic definition of the indol-3-yl methanone family, appearing in the same annex, covers it as well. This is therefore not a mere attachment by a generic clause: the name appears in full. Production, possession, transfer and use fall under the narcotics regime.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Classification
Family, origin and source verification
- Family
Synthetic CB receptor agonist › Research ligand or medicine
- Class
benzoylindole
- Verification
Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.
- Wikipedia (English)
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
- Grigoryev A, Kavanagh P, Melnik A. GC-MS detection of the urinary metabolites of AM-694, Drug Testing and Analysis, 2013 (new tab)PMID 22522907
- Bertol E, Vaiano F, Di Milia MG, Mari F. In vivo detection of AM-694 and its metabolites, Forensic Science International, 2015 (new tab)PMID 26295909
- Hutter M et al. Major in vivo metabolites of nine synthetic cannabinoid agonists including AM-694, Current Pharmaceutical Biotechnology, 2018 (new tab)PMID 29745330
- Apirakkan O, Gavrilović I, Cowan DA, Abbate V. In vitro phase I metabolic profile of AM-694, Chemical Research in Toxicology, 2020 (new tab)PMID 32301604
- Debruyne D, Le Boisselier R. Emerging drugs of abuse: current perspectives on synthetic cannabinoids, Substance Abuse and Rehabilitation, 2015 (table of CB1 and CB2 affinities) (new tab)PMID 26543389
- Lee W et al., Molecules, 2020: QSAR of the CB1 affinity of synthetic cannabinoids; measured pKi of AM-694: 6.553 (competition with [3H]SR141716A, ChemiScreen CB1 membranes) (new tab)PMID 33371501
- de Oliveira MC et al. Toxicity of Synthetic Cannabinoids in K2/Spice: A Systematic Review, Brain Sciences, 2023 (new tab)PMID 37508922
- Giorgetti A, Busardò FP, Tittarelli R, Auwärter V, Giorgetti R. Post-mortem toxicology of synthetic cannabinoid agonists, Frontiers in Psychiatry, 2020 (new tab)PMID 32523555
- Makriyannis A, Deng H. Cannabimimetic indole derivatives, patent WO 01/28557, University of Connecticut, 2001 (new tab)
- Willis PG, Katoch-Rouse R, Horti AG. Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand. J Labelled Comp Radiopharm, 2003 (new tab)DOI 10.1002/jlcr.720
- Order of 19 May 2015 amending the order of 22 February 1990 setting the list of substances classified as narcotics (Légifrance) (new tab)
- ANSM, consolidated list of substances classified as narcotics (Annex IV) (new tab)
- Consolidated Framework Decision 2004/757/JHA, annex of substances subject to control in the Union (EUR-Lex) (new tab)
- INCB, Green List of psychotropic substances under international control (new tab)
Identifiers
Names
- IUPAC name
- [1-(5-fluoropentyl)indol-3-yl]-(2-iodophenyl)methanone
- Other names
- AM694 · 1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole
Identifiers
- Formula
- C₂₀H₁₉FINO
- CAS
- 335161-03-0
- PubChem CID
- 9889172(new tab)
- InChIKey
- LFFIIZFINPPEMC-UHFFFAOYSA-N
- SMILES
- C1=
CC= C2C(= C1) C(= CN2CCCCCF) C(= O) C3= CC= CC= C3I
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.