Semi-synthetic cannabinoid
Narcotic: generic clauseSP-111SP-111 (Δ9-THC morpholinylbutyrate)
[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] 4-morpholin-4-ylbutanoate
Aliases.SP-111 · SP-111A · THC morpholinylbutyrate · morpholinylbutyrate de tétrahydrocannabinol
A water-soluble THC prodrug from the 1970s, with slow conversion and irregular pharmacokinetics.
Updated on
Level of detail
Identifiers
- Formula
- C₂₉H₄₃NO₄
- Molar mass
- 469.70 g·mol⁻¹
- CAS
- 55602-38-5
- PubChem CID
- 6453212
- Origin
- A semi-synthetic compound, absent from cannabis. It is obtained by esterification of the phenol of Δ9-THC with a butanoic acid bearing a morpholine ring, whose basic nitrogen allows the formation of water-soluble salts. It never left the field of research.
- InChIKey
- HAQNKTBQOIAWDB-DNQXCXABSA-N
In plain terms
SP-111 is THC made soluble in water, developed in the 1970s so that it could be injected in the laboratory. Once in the body it turns back slowly into THC, too slowly and too irregularly to have been genuinely useful.
Receptors and activity
- CB1Partial agonist
- CB2Partial agonist
- 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.
- Calm40
- Clarity15
- Sleep55
- Appetite60
- High55
Editorial estimate, not clinical.
Pharmacology
SP-111 is a water-soluble prodrug of Δ9-THC, obtained by esterification of the phenol with a butanoic acid bearing a morpholine ring. It answers a practical obstacle that long held back cannabinoid research: THC is almost insoluble in water, which rules out simple injectable formulations and requires oily or detergent vehicles whose own effects blur the interpretation of experiments. The basic nitrogen of the morpholine allows soluble salts to be formed and lifts that constraint. Segal published in 1978 in Brain Research a study of its effects on neuronal activity in the rat brain. The compound did not, however, live up to its promise: conversion to THC is slow and variable, which gives poorly predictable pharmacokinetics and a potency lower than that of the parent molecule. Those limits explain why it remained a historical landmark of cannabinoid prodrug chemistry rather than a lastingly adopted tool.
Route of preparation (chemical process)
No plant route. SP-111 is an ester of Δ9-THC: the phenol function at position 1 of the benzo[c]chromene skeleton is esterified by 4-(morpholin-4-yl)butanoic acid. The tertiary nitrogen of the morpholine ring, which can be protonated, is the element that confers water solubility in salt form. It is described here by chemical class only.
Legal framework
France
A narcotic. Annex IV of the arrêté of 22 February 1990 classifies as narcotics the tetrahydrocannabinols, their esters, their ethers and their salts, as well as the salts of those derivatives: SP-111, an ester of Δ9-THC, falls directly under that heading, as do its water-soluble salts.
European Union
Tetrahydrocannabinol and its esters fall under the national control ensured by Member States pursuant to the convention of 1971. SP-111 has never been the subject of a marketing authorisation application or of a specific European measure.
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- Semi-synthetic cannabinoid
- Origin
- A semi-synthetic compound, absent from cannabis. It is obtained by esterification of the phenol of Δ9-THC with a butanoic acid bearing a morpholine ring, whose basic nitrogen allows the formation of water-soluble salts. It never left the field of research.
- Status
- Narcotic: generic clause
References
Structured data
- InChIKey
- HAQNKTBQOIAWDB-DNQXCXABSA-N
- SMILES
- CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCCN4CCOCC4
- Formula
- C29H43NO4
- Molar mass
- 469.70 g·mol⁻¹
- CAS
- 55602-38-5
- PubChem CID
- 6453212
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.