{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"VONVJOGSLHAKOX-UHFFFAOYSA-N","prefName":"4-nonylphenylboronic acid","symbol":"4-NPBA","iupacName":"acide (4-nonylphényl)boronique","aliases":["4-nonylphenylboronic acid","acide para-nonylphénylboronique","4-NPBA"],"cas":"256383-45-6","pubchemCid":"4589192","chebiId":null,"smiles":"B(C1=CC=C(C=C1)CCCCCCCCC)(O)O","molecularFormula":"C15H25BO2","molecularWeight":248.17,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/4589192"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":"Acide arylboronique à chaîne alkyle longue. La molécule est d'une simplicité inhabituelle pour un inhibiteur enzymatique puissant : un benzène, une chaîne nonyle linéaire en position para, et une fonction acide boronique. La chaîne assure la reconnaissance par le canal lipophile de l'enzyme, qui accueille normalement la chaîne arachidonique du substrat, tandis que le bore agit sur la sérine catalytique. Ce mode d'action par mimétisme de l'état de transition distingue la classe des inhibiteurs covalents irréversibles comme le MAFP ou des carbamates comme l'URB597."},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"An entirely chemical route, described here by class only. The molecule combines a benzene ring bearing a linear nonyl chain at the para position with a boronic acid function. The boron atom, electron-deficient, is the functional element: it forms with the catalytic serine of hydrolases a tetrahedral adduct that mimics the transition state of the enzymatic reaction.","originNote":"A wholly synthetic compound. Arylboronic acids are very widely used organic chemistry reagents, notably for cross-couplings, and this one was available as a catalogue product before being recognised as an enzyme inhibitor. It has no natural occurrence and no human use.","discovered":"Identifié en 2008 par Minkkilä et collaborateurs, à l'université de Kuopio en Finlande, au terme d'une démarche inhabituelle : plutôt que de concevoir une molécule, l'équipe a évalué une série d'acides boroniques disponibles dans le commerce sur l'inhibition des deux hydrolases des endocannabinoïdes. Le composé s'est révélé le plus puissant de la série et a ouvert la voie des acides boroniques comme inhibiteurs de l'amidohydrolase."},"pharmacology":{"summaryFr":"4-nonylphenylboronic acid owes its entry into endocannabinoid pharmacology to a screening approach rather than to design work. Minkkilä and colleagues assessed in 2008 a series of commercial boronic acids, phenylic, heteroarylic, alkylic and alkenylic, for inhibition of the two enzymes that degrade the endocannabinoids. The general result was that these compounds preferentially inhibit fatty acid amide hydrolase, with effective concentrations ranging from the nanomolar to the low micromolar, and that eight of them also touch monoacylglycerol lipase in the micromolar range. The most potent proved to be the phenylboronic acid bearing a nonyl chain at the para position, with a median inhibitory concentration of 9.1 nanomolar at the amide hydrolase against 7.9 micromolar at monoacylglycerol lipase, that is a selectivity of about 870 times. The mechanism rests on a general property of boron. Electron-deficient, it accepts the lone pair of the catalytic serine and forms a tetrahedral adduct that reproduces the geometry of the transition state of the hydrolysis reaction, which constitutes a reversible but very tight inhibition, distinct from the irreversible covalent mechanism of the carbamates and ureas. That work founded the boronic acids as a class of amide hydrolase inhibitors and was extended by later work on boronic acids directed at other lipases, notably endothelial lipase.","receptorSummaryFr":"A potent and selective inhibitor of fatty acid amide hydrolase. Minkkilä and colleagues measured a median inhibitory concentration of 9.1 nanomolar at that enzyme, against 7.9 micromolar at monoacylglycerol lipase, that is a selectivity of about 870 times in favour of the former. That value made it the most potent compound of the series of commercial boronic acids assessed, and established it as a lead structure for this class of inhibitors. The compound has no described direct action on cannabinoid receptors; its expected effect passes through the elevation of anandamide concentrations.","binding":[{"target":"FAAH","efficacy":"antagonist","relativeActivity":90,"reported":"IC50 = 9,1 nM (Minkkilä et coll. 2008)","confidence":"medium"},{"target":"MAGL","efficacy":"antagonist","relativeActivity":25,"reported":"IC50 = 7,9 µM ; sélectivité d'environ 870 fois pour la FAAH","confidence":"medium"}],"references":[{"label":"Minkkilä et coll. 2008 : découverte des acides boroniques comme inhibiteurs puissants de la FAAH","pmid":"18983140","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/18983140/"}]},"pharmacokinetics":"Aucune donnée de pharmacocinétique n'est publiée, ni chez l'animal ni chez l'humain. Le composé a été caractérisé exclusivement in vitro sur préparations enzymatiques. Aucune dose humaine n'est caractérisée et rien n'autorise à en extrapoler une.","metabolism":"Aucune étude de métabolisme n'est publiée. Les acides boroniques sont en général sujets à oxydation du bore et à formation d'esters boroniques réversibles avec les diols biologiques, ce qui influencerait leur devenir dans un organisme, mais cette description reste une attente de classe et non un résultat mesuré pour ce composé.","detection":"La molécule ne figure dans aucun panel de dépistage et n'a pas d'intérêt médicolégal. Sa quantification relève des méthodes analytiques de laboratoire, par chromatographie liquide couplée à la spectrométrie de masse.","subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":20},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":10},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":15},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":10},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":10}],"doseRanges":null,"humanDataCharacterised":false},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":true,"bannerTextFr":"Aucune dose humaine caractérisée : données animales / in vitro uniquement. Profil d'effet, marge de sécurité et toxicité aiguë non documentés en clinique humaine.","toxicologyFr":"Aucune donnée de toxicologie humaine n'est disponible et aucune dose humaine n'est caractérisée. Le composé n'a jamais été administré à l'humain. Il convient de noter que la chaîne nonylphényle est un motif structurel apparenté à celui des nonylphénols, substances par ailleurs surveillées pour leurs propriétés de perturbation endocrinienne ; cette parenté structurale ne constitue pas une donnée toxicologique sur la molécule elle-même, mais elle justifie de ne pas présumer son innocuité."},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"Unscheduled","frScheduleStatus":"unscheduled","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":"Non inscrit aux conventions de contrôle","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Réactif de chimie ; non contrôlé","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Non inscrit ; usage de laboratoire uniquement","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Minkkilä et coll. 2008 : découverte des acides boroniques comme inhibiteurs puissants de la FAAH","pmid":"18983140","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/18983140/"}],"meta":{"slug":"4-npba","url":"https://en.phytogrammes.com/wiki/4-npba","lastVerified":"2026-05-01","dataUpdatedAt":"2026-08-16","confidence":"medium","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}