Serinolamide A

Cannabinomimetic lipid from a marine cyanobacterium, moderate affinity for CB1.

C₂₃H₄₅NO₃

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: (E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]-N-methyloctadec-4-enamide
Other names: (4E)-N-[(2R)-1-Hydroxy-3-methoxy-2-propanyl]-N-methyl-4-octadecenamide

Identifiers

Formula: C₂₃H₄₅NO₃
Molar mass: 383.60 g/mol
PubChem CID: 56597771(new tab)
ChEBI: CHEBI:69065(new tab)
InChIKey: CJAVPRNATZCNLN-NBRGKURFSA-N

Class

Family: ECS modulator (research)

Legal status

Status: Unscheduled

See the legal framework

Updated on 13 October 2026

Receptors and activity

CB1Agonist40 out of 100
Ki 1,3 µM (Gutiérrez et coll., 2011), effet agoniste modéré rapporté par les auteurs
CB2Modulator5 out of 100
IC50 supérieure à 10 µM (Gutiérrez et coll., 2011) ; aucune constante d'affinité publiée

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

Subjective signature

Calm: 15 out of 100; Relaxation of body and mind; reduced mental noise without marked drowsiness.
Clarity: 8 out of 100; Sustained attention and clear thinking; functional lucidity, not euphoria.
High: 5 out of 100; Euphoria and sensory intensity; altered perception of time and space.
Appetite: 5 out of 100; Stimulation of hunger and of taste appreciation (the “munchies” effect).
Sleep: 10 out of 100; Sedative effect: aids sleep onset and the continuity of deep sleep.

Editorial estimate, not clinical.

Pharmacology

Serinolamide A is a fatty acid amide isolated in 2011 from the marine cyanobacterium Lyngbya majuscula, collected in Papua New Guinea, by Gutiérrez et al. Its structure, which recalls that of anandamide, led its authors to present it as a cannabinomimetic lipid. It displaces a radioligand from the human CB1 receptor with a Ki of 1.3 µM, a moderate affinity that the authors consider selective for this receptor, and it does not displace half of the radioligand from CB2 at 10 µM. No human or pharmacokinetic data has been published, and a total synthesis was described in 2019.

Key sources.

History

Source: Marine cyanobacterium Lyngbya majuscula, collected off New Ireland (Papua New Guinea) in 2005. Serinolamides have also been described from a cyanobacterium of the genus Okeania collected in the Red Sea (Petitbois et al., 2017).

Origin (research tool)

No biosynthetic pathway has been demonstrated experimentally. The authors of the isolation put forward a hypothesis: the fatty chain would derive from a polyketide synthase (PKS) pathway, the serinol unit from serine, and the methyl groups would be introduced by S-adenosylmethionine (SAM)-dependent methyltransferases. A total synthesis published in 2019 prepares the molecule in the laboratory by a convergent approach (Ghotekar et al., 2019).

Legal framework

European Union: No harmonised European Union control measure for serinolamide A has been identified in the sources consulted: the EU level sets no harmonised measure for this molecule, and control falls under national law.
France: Serinolamide A is not named on the French narcotics list (ANSM consolidated list, updated 16 February 2026). Its structure does not meet the generic family definitions of this list: it has no indole, indazole, pyrrole, naphthyl, cyclohexylphenol or thiazole core, nor the benzo[c]chromene nucleus, covered by a clause of the ANSM decision of 22 May 2024. It is also not on the INCB Green List 2026 (1971 Convention).

Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.

References

Structured data

SMILES: CCCCCCCCCCCCC/C=C/CCC(=O)N(C)[C@H](CO)COC
InChIKey: CJAVPRNATZCNLN-NBRGKURFSA-N

Machine-readable entry (JSON)

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