ECS modulator (research)
UnscheduledAA-5-HTN-arachidonoylserotonin
Aliases.AA-5-HT · N-arachidonoyl serotonin · arachidonoyl sérotonine · AA-5HT
A mixed FAAH and TRPV1 blocker, a reference tool at the intersection of the cannabinoid and vanilloid systems.
Updated on
Level of detail
Identifiers
- Formula
- C₃₀H₄₂N₂O₂
- Molar mass
- 462.70 g·mol⁻¹
- CAS
- 187947-37-1
- PubChem CID
- 10027372
- Origin
- A synthetic compound, designed in the laboratory by formal conjugation of arachidonic acid and serotonin. It is used as a pharmacological tool and as a lead structure for the design of dual-mechanism analgesics, with no authorised human use and no circulation as a consumer product.
- InChIKey
- QJDNHGXNNRLIGA-DOFZRALJSA-N
In plain terms
N-arachidonoylserotonin is a laboratory molecule that acts in two ways at once: it prevents the destruction of anandamide, the cannabinoid produced by the body, and it blocks a channel involved in the sensation of burning. That dual action makes it a research tool for pain.
Receptors and activity
- FAAHAntagonist
- TRPV1CI50 de 37 à 40 nM contre 100 nM de capsaïcine (TRPV1 recombinant de rat et humain, Maione 2007)Antagonist
- CB1Modulator
- 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.
- Calm60
- Clarity30
- Sleep35
- Appetite20
- High25
Editorial estimate, not clinical.
Pharmacology
N-arachidonoylserotonin is a mixed blocker of the endocannabinoid and endovanilloid systems, widely used as a pharmacological tool. It inhibits FAAH, the hydrolase that degrades anandamide, and antagonises the TRPV1 channel. Maione and colleagues (2007) established that second aspect on HEK-293 cells expressing recombinant rat or human TRPV1, with an IC50 of 37 to 40 nM against 100 nM capsaicin, and showed marked analgesic activity in several pain models in rats and mice, from the formalin test to chronic constriction of the sciatic nerve. Dissection of the mechanism is instructive: the effect is partly lifted by AM251, a CB1 antagonist, which confirms passage through the elevation of anandamide and indirect activation of CB1; it is also reproduced by TRPV1 antagonists given alone, and lifted by them, which confirms the vanilloid component. That dual activity explains its efficacy on acute pain as on chronic peripheral pain. Anxiolytic-type effects and an action on contextual fear memory have also been reported.
Origin (research tool)
No plant biosynthetic route. The molecule joins by an amide bond the twenty-carbon polyunsaturated chain of arachidonic acid and the indole core of serotonin. It belongs to the N-acylserotonin class, described here by chemical class only.
Legal framework
France
A research compound, not listed in Annex IV of the arrêté of 22 February 1990 and not covered by the generic clauses targeting synthetic cannabinoids, which concern indole, indazole or related skeletons bearing alkyl chains. No human use is authorised and the molecule does not circulate as a consumer product.
European Union
No harmonised control at Union level and no listing under the international conventions of 1961 and 1971. The compound holds the status of a laboratory reagent.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- ECS modulator (research)
- Origin
- A synthetic compound, designed in the laboratory by formal conjugation of arachidonic acid and serotonin. It is used as a pharmacological tool and as a lead structure for the design of dual-mechanism analgesics, with no authorised human use and no circulation as a consumer product.
- Status
- Unscheduled
References
Structured data
- InChIKey
- QJDNHGXNNRLIGA-DOFZRALJSA-N
- SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCC1=CNC2=C1C=C(C=C2)O
- Formula
- C30H42N2O2
- Molar mass
- 462.70 g·mol⁻¹
- CAS
- 187947-37-1
- PubChem CID
- 10027372
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.