Synthetic cannabinoid (SCRA)
UnscheduledPravadolinePravadoline (WIN 48098)
(4-methoxyphenyl)-[2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]methanone
Aliases.WIN 48098 · WIN 48098-6 · pravadoline maleate · BRL-38227
The founding aminoalkylindole: a 1980s anti-inflammatory that became the ancestor of the synthetic cannabinoids.
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
- C₂₃H₂₆N₂O₃
- Molar mass
- 378.50 g·mol⁻¹
- CAS
- 92623-83-1
- PubChem CID
- 56463
- Origin
- A wholly synthetic molecule, absent from cannabis as from any living organism. It was designed within a pharmaceutical programme and has no significant presence on the consumer product market; its chemical progeny, by contrast, has spread far beyond the laboratory.
- InChIKey
- MEUQWHZOUDZXHH-UHFFFAOYSA-N
In plain terms
Pravadoline is an anti-inflammatory designed in the 1980s that eased pain far more than it should have. In looking for why, researchers discovered that it acted on the cannabis receptors: it is the ancestor of the whole family of indole-cored synthetic cannabinoids.
Receptors and activity
- CB1Agonist
- COXAntagonist
- 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.
- Calm35
- Clarity20
- Sleep30
- Appetite25
- High25
Editorial estimate, not clinical.
Pharmacology
Pravadoline (WIN 48098) is the founding molecule of the aminoalkylindoles, and thereby of the entire lineage of indole-cored synthetic cannabinoids. Designed by the Sterling group in the 1980s as a non-steroidal anti-inflammatory related to indomethacin, it did indeed inhibit prostaglandin synthesis. The anomaly lay in its analgesic effect, obtained at doses ten times lower than the anti-inflammatory dose and insensitive to naloxone: neither cyclooxygenase nor opioid receptors could account for it. Pravadoline proved to be an agonist of cannabinoid receptors, the first of a then unknown chemical class. Optimisation of the series subsequently dissociated the two activities, the effect on prostaglandins fading as CB1 activity strengthened, and led to WIN 55,212-2, a reference agonist still used today, then to the JWH series that fed the fake cannabis market. Clinical development of pravadoline itself was abandoned.
Origin (pharmaceutical research → illicit market)
No biological route. Pravadoline is an aminoalkylindole obtained by synthesis: an indole core bears at position 1 a morpholinoethyl chain, at position 2 a methyl, and at position 3 a ketone function linking a 4-methoxyphenyl ring. It is described here by chemical class only.
Legal framework
France
Pravadoline is not listed by name in Annex IV of the arrêté of 22 February 1990. Its structure, an indole ketone bearing an aminoalkyl chain and a methoxyphenyl head, does not correspond to the naphthoylindole families or to the carboxamide families added by the arrêté of 31 March 2017. In practice it holds the status of a research compound, with no authorised human use and no commercialisation.
European Union
No harmonised control at Union level and no listing under the international conventions of 1961 and 1971. Clinical development of the molecule as an analgesic was abandoned and it never obtained a marketing authorisation in a Member State.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Synthetic cannabinoid (SCRA)
- Origin
- A wholly synthetic molecule, absent from cannabis as from any living organism. It was designed within a pharmaceutical programme and has no significant presence on the consumer product market; its chemical progeny, by contrast, has spread far beyond the laboratory.
- Status
- Unscheduled
References
Structured data
- InChIKey
- MEUQWHZOUDZXHH-UHFFFAOYSA-N
- SMILES
- CC1=C(C2=CC=CC=C2N1CCN3CCOCC3)C(=O)C4=CC=C(C=C4)OC
- Formula
- C23H26N2O3
- Molar mass
- 378.50 g·mol⁻¹
- CAS
- 92623-83-1
- PubChem CID
- 56463
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.