Eburnamonine

Eburnamonine at a Glance

Eburnamonine is a monoterpenoid indole alkaloid of the eburnamine–vincamine group, the alkaloid family that defines lesser periwinkle (Vinca minor) and its relatives in the dogbane family (Apocynaceae). Its most useful single fact is that it is not only a phytochemical: the levorotatory form, (−)-eburnamonine, is the drug vinburnine, sold in France as Cervoxan and listed among the four eburnamine–vincamine alkaloids approved for clinical use — with vincamine, brovincamine and the semi-synthetic vinpocetine ^{25,28Reference 25Wang H et al. · 2026ReviewThe golden decade of eburnamine-vincamine alkaloid synthesis: 2015 to present — reviewView study →Reference 28Chauveau E et al. · 1998Case reportChauveau E, et al. (1998). [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)] — case report. Gastroentérologie Clinique et Biologique. https://pubmed.ncbi.nlm.nih.gov/9762227/View study →}.

That drug identity is what separates eburnamonine from most plant alkaloids here. It means there is an actual human record to look at rather than only in-vitro assays: small double-blind trials in cerebrovascular patients, oxygen-transport studies in elderly volunteers, and published human pharmacokinetics for the parent drug and its 6-hydroxy metabolite ^{5,7,8,17Reference 5Ferretti PG et al. · 1982Clinical trialEffects of acute and chronic treatment with (-)eburnamonine on the tissue supply of oxygen — clinical trialView study →Reference 7Marolda M et al. · 1978Clinical trialClinical evaluation of (-)eburnamonine in comparison with nicergoline in patients suffering from chronic brain ischemia — clinical trialView study →Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →Reference 17Sado PA et al. · 1988Sado PA, et al. (1988). [Simultaneous determination of vinburnine and 6-hydroxyvinburnine in human plasma by high-performance liquid chromatography]. Journal of Chromatography. https://pubmed.ncbi.nlm.nih.gov/3243809/View study →}. It also means the record can be judged, and the judgement is not flattering. The trials were small, old and mostly conducted before modern standards; a Drugs review of the whole “cerebroactive” class concluded that no therapeutic indication could be derived from the available evidence ^{9Reference 9Spagnoli A et al. · 1983ReviewSpagnoli A, et al. (1983). ‘Cerebroactive’ drugs. Clinical pharmacology and therapeutic role in cerebrovascular disorders — review. Drugs. https://pubmed.ncbi.nlm.nih.gov/6349963/View study →}; and one head-to-head pharmacological comparison found vinburnine simply inactive in the ischaemia models where it was expected to work ^{15Reference 15Barzaghi F et al. · 1986A comparison of some of the pharmacological properties of the new eburnamenine derivative vindeburnol with those of vincamine, vinburnine, dihydroergotoxine mesilate and nicergolineView study →}.

The second thing eburnamonine is known for is quieter but more current: it is the molecule researchers put beside vincamine and vinpocetine when they want a comparator. That is how it appears in the V. minor literature — as the third arm of transport and metabolic-stability assays, where it turned out to be the most metabolically stable of the three ^{10Reference 10Fandy TE et al. · 2016In vitroIn vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonineView study →}.

Eburnamonine and Vinburnine Are the Same Molecule

The names are used interchangeably in the literature and it is easy to read two half-empty files as two compounds.

• Eburnamonine is the natural-product name. It comes from Hunteria eburnea, the West African apocynaceous tree from which it was first isolated in 1960 ^{1Reference 1Bartlett MF · 1960The Alkaloids of Hunteria eburneaView study →}.
• Vinburnine is the International Nonproprietary Name given to the (−)-enantiomer when it was developed as a drug. Older papers also call it l-eburnamonine or, structurally, 16-oxoeburnane ^{2Reference 2Linée P et al. · 1978Cerebral metabolic, hemodynamic and antihypoxic properties of l-eburnamonineView study →}.
• Vincamone is a further synonym, and Cervoxan is the French brand under which vinburnine was prescribed ^{28Reference 28Chauveau E et al. · 1998Case reportChauveau E, et al. (1998). [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)] — case report. Gastroentérologie Clinique et Biologique. https://pubmed.ncbi.nlm.nih.gov/9762227/View study →}.

The stereochemistry matters and is worth stating carefully. The pharmacology below is essentially all for the (−)/l-enantiomer; racemic (±)-eburnamonine is a separate registered entity, and the synthetic literature treats (−)-eburnamonine, (+)-eburnamonine, (+)-epi-eburnamonine and (−)-20-epi-eburnamonine as distinct targets ^{22,25Reference 22Chong KW et al. · 2017Biosynthetic enantiodivergence in the eburnane alkaloids from KopsiaView study →Reference 25Wang H et al. · 2026ReviewThe golden decade of eburnamine-vincamine alkaloid synthesis: 2015 to present — reviewView study →}. Nature is not tidy about it either. Work on the eburnane alkaloids of Kopsia found genuine biosynthetic enantiodivergence: an alkaloid can occur in the same plant with a configuration opposite to the usual one, and the enantiomeric distribution can shift with the geographic origin of the material ^{22Reference 22Chong KW et al. · 2017Biosynthetic enantiodivergence in the eburnane alkaloids from KopsiaView study →}. So “eburnamonine was detected in this plant” does not by itself tell you which enantiomer — or which mixture — was present.

One thing eburnamonine is not. It has nothing to do with vinblastine or vincristine. Those are bisindole alkaloids from Catharanthus roseus (Madagascar periwinkle), a different genus with a completely different clinical story — cytotoxic chemotherapy. Nor is it vinpocetine, which is a semi-synthetic ethyl ester of apovincamine and occurs in no plant at all.

The Benchmark Comparator

The reason eburnamonine keeps appearing in Vinca minor papers is not that anyone is developing it. It is that it makes a useful third arm.

In the study that anchors this role, vincamine, vinpocetine and eburnamonine were run side by side through liver-microsome stability and brain-barrier transporter assays. Two results came out of it. First, eburnamonine’s intrinsic clearance was significantly lower than both vincamine’s and vinpocetine’s — it is the metabolically toughest of the three. Second, all three showed minimal interaction with the efflux transporters P-glycoprotein and BCRP, which is the pharmacological argument for saying the class can reach the brain rather than being pumped back out at the barrier ^{10Reference 10Fandy TE et al. · 2016In vitroIn vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonineView study →}. The authors’ conclusion was explicitly forward-looking: eburnamonine is a reasonable starting point for central-nervous-system neuroprotective and anticancer development.

That is a genuinely informative comparison, but it should be read for what it is — an in-vitro ranking, not a demonstration that eburnamonine works better in people. The one human comparison that exists in this family points the other way: in a rodent-model comparison of five cerebroactive agents, vincamine and dihydroergotoxine gave limited benefit while vinburnine and nicergoline were ineffective ^{15Reference 15Barzaghi F et al. · 1986A comparison of some of the pharmacological properties of the new eburnamenine derivative vindeburnol with those of vincamine, vinburnine, dihydroergotoxine mesilate and nicergolineView study →}.

What It's Used For

The evidence divides into three eras. A 1978–1990 European drug programme produced small double-blind trials and oxygen-transport studies; a 1996–2004 receptor-pharmacology thread found something genuinely distinctive at muscarinic receptors; and a 2016–2025 revival uses it as an in-vitro comparator and, most recently, as an oncology-repurposing candidate.

Evidence by IndicationStrength of support · Beta

Support is an experimental score — weighted by study type (human > animal > in vitro) and volume. A beta, not a validated metric. Every row here is for the isolated molecule, usually as the pharmaceutical (−)-enantiomer; none of it is whole-plant evidence.

01Cerebral antihypoxia (oxygen delivery)Shaky40%Animal hypoxia/ischaemia models + small human 2,3-DPG and P50 studies ^{2,3,4,5,6,35,36Reference 2Linée P et al. · 1978Cerebral metabolic, hemodynamic and antihypoxic properties of l-eburnamonineView study →Reference 3Villa RF et al. · 1978Effect of (-)eburnamonine, papaverine and UDP-glucose on cerebral energy state during and after experimental hypoxia and ischaemia in beagle dogView study →Reference 4Linée P et al. · 1981Experimental approach of activity and mechanism(s) of action of drugs used in cerebral metabolic insufficiencyView study →Reference 5Ferretti PG et al. · 1982Clinical trialEffects of acute and chronic treatment with (-)eburnamonine on the tissue supply of oxygen — clinical trialView study →Reference 6Louajri A et al. · 1999AnimalRed blood cell metabolism and hemoglobin oxygen affinityView study →Reference 35Acciavatti A et al. · 1990In vitroAcciavatti A, et al. (1990). [The effects of vinburnine on the blood rheology parameters and on the oxyhemoglobin dissociation curve and 2,3-diphosphoglycerate. In vitro research]. Recenti Progressi in Medicina. https://pubmed.ncbi.nlm.nih.gov/2287807/View study →Reference 36Domini L et al. · 1990AnimalDomini L, et al. (1990). [The effects of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research]. Recenti Progressi in Medicina. https://pubmed.ncbi.nlm.nih.gov/2287808/View study →}

02Cerebrovascular / cognitive symptoms (elderly)Shaky32%Two small 1978–86 double-blind trials + a head-injury study, against a negative class review and a negative comparison ^{7,8,9,15,30Reference 7Marolda M et al. · 1978Clinical trialClinical evaluation of (-)eburnamonine in comparison with nicergoline in patients suffering from chronic brain ischemia — clinical trialView study →Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →Reference 9Spagnoli A et al. · 1983ReviewSpagnoli A, et al. (1983). ‘Cerebroactive’ drugs. Clinical pharmacology and therapeutic role in cerebrovascular disorders — review. Drugs. https://pubmed.ncbi.nlm.nih.gov/6349963/View study →Reference 15Barzaghi F et al. · 1986A comparison of some of the pharmacological properties of the new eburnamenine derivative vindeburnol with those of vincamine, vinburnine, dihydroergotoxine mesilate and nicergolineView study →Reference 30Facciolla D et al. · 1983Clinical trialClinical and electrophysiologic changes produced by (-)eburnamonine in acute and post-acute stages of head injuries — clinical trialView study →}

03Muscarinic allosteric modulationShaky28%Well-characterised in-vitro allosteric pharmacology at M1–M4, micromolar, no in-vivo translation ^{12,13Reference 12Proska J et al. · 1996Positive allosteric action of eburnamonine on cardiac muscarinic acetylcholine receptorsView study →Reference 13Maksay G et al. · 2004Vinburnine decelerates [3H]N-methylscopolamine binding to recombinant human muscarinic M1-M4 acetylcholine receptorsView study →}

04Learning and memory (animal models)Shaky20%One rodent amnesia/seizure study, mechanistically consistent with the muscarinic data ^{14Reference 14Drago F et al. · 1990Effects of vinburnine on experimental models of learning and memory impairmentsView study →}

05Oncology repurposing (preclinical)Shaky18%Two 2025 preclinical papers (melanoma immunotherapy, nasopharyngeal radiosensitisation) ^{31,32Reference 31Zhu S et al. · 2025Vinburnine potentiates anti-PD1 immunotherapy in melanoma through IL-24 secretion via P38/MAPK/ATF3 signalingView study →Reference 32Chen J et al. · 2025Vinburnine sensitizes radiotherapy efficacy in nasopharyngeal carcinoma by triggering pyroptosis and immune responses via activation of the EDAR-NFκB pathwayView study →}

Mechanisms

Two of these are the page’s real content. The 2,3-DPG/P50 shift is the only mechanism with corroborating human measurements, and the inverted muscarinic allostery relative to vincamine is the one place where eburnamonine is pharmacologically distinct from the alkaloid it is usually treated as a shadow of.

Pharmacokinetics

Because vinburnine was a marketed drug, some human pharmacokinetics exist — but they are formulation studies rather than a modern ADME package. A validated HPLC assay measured vinburnine and its metabolite 6-hydroxyvinburnine in human plasma down to 5 ng/mL, establishing 6-hydroxylation as the principal identified human metabolic route ^{17Reference 17Sado PA et al. · 1988Sado PA, et al. (1988). [Simultaneous determination of vinburnine and 6-hydroxyvinburnine in human plasma by high-performance liquid chromatography]. Journal of Chromatography. https://pubmed.ncbi.nlm.nih.gov/3243809/View study →}. That is corroborated from an unexpected direction: microbial biotransformation of (−)-eburnamonine by Mucor circinelloides and Streptomyces violens produced (6R)- and (6S)-6-hydroxyeburnamonine plus (18S)-18-hydroxyeburnamonine, and the parent and all three hydroxylated metabolites protected mice against potassium-cyanide intoxication — so the major metabolite is not pharmacologically inert ^{20Reference 20Adachi T et al. · 1993Microbial hydroxylation of (-)-eburnamonine by Mucor circinelloides and Streptomyces violensView study →}.

The clinical problem was absorption. Successive bioavailability studies in man tested microgranule versus capsule formulations ^{19Reference 19Sado PA et al. · 1985Sado PA, et al. (1985). [Relative bioavailability of vinburnine in man (microgranules/gels)]. Journal de Pharmacie de Belgique. https://pubmed.ncbi.nlm.nih.gov/4087124/View study →}, an oral liquid form, and combination with ascorbic acid ^{18Reference 18Sado PA et al. · 1989Sado PA, et al. (1989). [The oral liquid form of vinburnine: biopharmaceutics]. Journal de Pharmacie de Belgique. https://pubmed.ncbi.nlm.nih.gov/2724048/View study →}, and the recurring finding is “very important, and well known interindividual variations” in exposure; the drops formulation increased absorption rate over capsules ^{18Reference 18Sado PA et al. · 1989Sado PA, et al. (1989). [The oral liquid form of vinburnine: biopharmaceutics]. Journal de Pharmacie de Belgique. https://pubmed.ncbi.nlm.nih.gov/2724048/View study →}. Formulation chemists went as far as complexing vinburnine with β- and γ-cyclodextrins to improve its behaviour in solution and in the solid state ^{26Reference 26Giordano F et al. · 1988Complexation behavior of vinburnine with beta and gamma cyclodextrins in aqueous solution and in the solid stateView study →} — the signature of a poorly soluble, formulation-limited molecule.

In vitro, the picture is more favourable: vinburnine’s intrinsic clearance is significantly lower than vincamine’s or vinpocetine’s, and it shows minimal interaction with P-glycoprotein or BCRP, so it is not actively pumped out of the brain ^{10Reference 10Fandy TE et al. · 2016In vitroIn vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonineView study →}. No published human half-life, oral bioavailability percentage, Cmax or volume of distribution was located — a real hole, and one that matters, because a molecule with erratic absorption and no stated bioavailability figure cannot be argued from in-vitro potency alone.

Clinical Trials

The clinical footprint is entirely historical: a handful of small double-blind European studies conducted between 1978 and 1986 in chronic brain ischaemia, cerebrovascular disorders and head injury ^{7,8,30Reference 7Marolda M et al. · 1978Clinical trialClinical evaluation of (-)eburnamonine in comparison with nicergoline in patients suffering from chronic brain ischemia — clinical trialView study →Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →Reference 30Facciolla D et al. · 1983Clinical trialClinical and electrophysiologic changes produced by (-)eburnamonine in acute and post-acute stages of head injuries — clinical trialView study →}, plus oxygen-transport studies in elderly volunteers ^{5,36Reference 5Ferretti PG et al. · 1982Clinical trialEffects of acute and chronic treatment with (-)eburnamonine on the tissue supply of oxygen — clinical trialView study →Reference 36Domini L et al. · 1990AnimalDomini L, et al. (1990). [The effects of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research]. Recenti Progressi in Medicina. https://pubmed.ncbi.nlm.nih.gov/2287808/View study →}. There are no registered modern trials, no meta-analyses and no dementia-specific randomised evidence for eburnamonine or vinburnine, and the contemporaneous class review found the positive results indistinguishable from random symptom fluctuation ^{9Reference 9Spagnoli A et al. · 1983ReviewSpagnoli A, et al. (1983). ‘Cerebroactive’ drugs. Clinical pharmacology and therapeutic role in cerebrovascular disorders — review. Drugs. https://pubmed.ncbi.nlm.nih.gov/6349963/View study →}.

Last checked: July 2026.

Isolate vs. Plant Studies

Every finding here is isolate data, and almost all of it is the pharmaceutical (−)-enantiomer at pharmaceutical doses — 60–180 mg/day orally, or 40–100 mg by infusion ^{5,7,8,36Reference 5Ferretti PG et al. · 1982Clinical trialEffects of acute and chronic treatment with (-)eburnamonine on the tissue supply of oxygen — clinical trialView study →Reference 7Marolda M et al. · 1978Clinical trialClinical evaluation of (-)eburnamonine in comparison with nicergoline in patients suffering from chronic brain ischemia — clinical trialView study →Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →Reference 36Domini L et al. · 1990AnimalDomini L, et al. (1990). [The effects of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research]. Recenti Progressi in Medicina. https://pubmed.ncbi.nlm.nih.gov/2287808/View study →}. In one sense that is a strength: nothing here is an extract assay where eburnamonine is one of a dozen co-occurring alkaloids, and the human trials tested the pure compound at a stated dose.

The weakness is on the other side of the bridge. No study has tested Vinca minor herb, tea, tincture or extract for any of these effects, and eburnamonine’s contribution to whatever V. minor preparations do is unknown. The one quantitative study of V. minor macerates found four indole alkaloids — vincamine, 1,2-dehydroaspidospermidine, vincaminoreine and eburnamonine — with vincamine the most abundant at 2.459 mg/100 g dry weight in leaves, and eburnamonine detected but not the headline compound ^{21Reference 21Neculai AM et al. · 2023Determination of active ingredients, mineral composition and antioxidant properties of hydroalcoholic macerates of Vinca minor L. plant from the Dobrogea areaView study →}. At that order of magnitude, an ordinary herbal preparation delivers a fraction of a milligram of total alkaloid — several orders below the 60 mg drug dose. Whatever lesser periwinkle does traditionally, this molecule at that exposure is not a plausible explanation for it.

The same caution applies in reverse to the class. Findings for vincamine, apovincamine and vinpocetine are frequently written up as “eburnamine alkaloid” properties ^{11Reference 11Vas A · 2005ReviewEburnamine derivatives and the brain — reviewView study →}, but the muscarinic work shows the direction of an effect can invert between two structurally close members of this family ^{12Reference 12Proska J et al. · 1996Positive allosteric action of eburnamonine on cardiac muscarinic acetylcholine receptorsView study →}. Class-level transfer is not safe here.

Prevalence in Nature

Eburnamonine occurs across the Apocynaceae, always as a minor alkaloid rather than a dominant one, and the botanical record is more about which genera than how much.

• Hunteria eburnea — the type source. Eburnamine, isoeburnamine, eburnamenine and eburnamonine were isolated from this West African tree in 1960, and the compound takes its name from the species ^{1Reference 1Bartlett MF · 1960The Alkaloids of Hunteria eburneaView study →}. The related Hunteria zeylanica yields hydroxylated relatives — 14β-hydroperoxy-eburnamine and 18α-hydroxy-eburnamine were described from Hainan material ^{23Reference 23Liu Q et al. · 2016Two new indole alkaloids from Hunteria zeylanicaView study →}.
• Vinca minor — HPLC analysis of hydroalcoholic macerates of leaf and stem from Romanian material identified eburnamonine as one of four indole alkaloids present, alongside vincamine (2.459 ± 0.035 mg/100 g dry weight in leaves), 1,2-dehydroaspidospermidine and vincaminoreine ^{21Reference 21Neculai AM et al. · 2023Determination of active ingredients, mineral composition and antioxidant properties of hydroalcoholic macerates of Vinca minor L. plant from the Dobrogea areaView study →}. This is the occurrence that puts it here, and it is a qualitative detection, not a quantified one.
• Kopsia — the eburnane alkaloids of this Southeast Asian genus are the best-studied natural source for stereochemistry. 19-Hydroxy-(−)-eburnamonine was isolated from Kopsia arborea twigs ^{24Reference 24Cheenpracha S et al. · 2014Monoterpene indole alkaloids from the twigs of Kopsia arboreaView study →}, and a systematic absolute-configuration study of Malaysian Kopsia material established the enantiodivergence described above: an alkaloid may occur with the configuration opposite to the common one in the same plant, and geographic provenance can shift the enantiomeric distribution ^{22Reference 22Chong KW et al. · 2017Biosynthetic enantiodivergence in the eburnane alkaloids from KopsiaView study →}.

No percentage-of-dry-weight figure for eburnamonine in any species was located, in Vinca minor or elsewhere. Commercially, V. minor is farmed for vincamine, not for eburnamonine; eburnamonine is a companion alkaloid in that extraction stream rather than a target of it.

Discovery & Synthesis

First isolation, 1960. Bartlett and Taylor isolated eburnamonine from Hunteria eburnea Pichon and published its structure alongside those of eburnamine, isoeburnamine and eburnamenine, together with a synthesis of the racemate — establishing the whole eburnamine skeleton in a single paper ^{1Reference 1Bartlett MF · 1960The Alkaloids of Hunteria eburneaView study →}. Eburnamine and isoeburnamine are diastereoisomeric pentacyclic indoles that can be oxidised to eburnamonine, an N-acylindole; the etymology runs directly from the species name.

First total synthesis, 1965. Wenkert reported a synthesis of dl-eburnamonine as part of a general programme on indole-alkaloid synthesis ^{27Reference 27Wenkert E et al. · 1965General methods of synthesis of indole alkaloidsView study →}. Because its rigid pentacyclic skeleton carries a quaternary stereocentre, eburnamonine has since become a standing benchmark target for asymmetric methodology — used to showcase enantioselective imine hydrogenation/lactamisation cascades, photocatalytic radical cascades, iridium-catalysed reductive annulation, alkene cyanoamidation, and nickel-catalysed enantioconvergent substitution, among others ^{25Reference 25Wang H et al. · 2026ReviewThe golden decade of eburnamine-vincamine alkaloid synthesis: 2015 to present — reviewView study →}. A 2026 Natural Product Reports review covering 2015 onward frames this as “the golden decade” of eburnamine–vincamine synthesis and confirms the clinical status of the four approved members of the group ^{25Reference 25Wang H et al. · 2026ReviewThe golden decade of eburnamine-vincamine alkaloid synthesis: 2015 to present — reviewView study →}.

Manufacture and derivatives. Semi-synthesis from the far more abundant vincamine is the practical route into this skeleton — 15-methylene-eburnamonine, for instance, is made from (+)-vincamine ^{34Reference 34Woods JR et al. · 2013Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity and mechanistic studyView study →} — and derivatisation of (−)-eburnamonine itself (α-methylenation of its hindered carbonyl) has produced cytotoxic analogues ^{33Reference 33Riofski MV et al. · 2011Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonineView study →}. As with the rest of the group, the pharmaceutical supply chain has historically started from Vinca minor alkaloid extraction rather than from total synthesis.

Patents: not yet researched.

Toxicity & Safety

Eburnamonine carries a moderate flag. This is not a food-level phytochemical: as vinburnine it was a prescription cerebral vasoactive drug given at 60–180 mg/day, with dose-dependent gastrointestinal effects in trial and two distinct classes of published adverse reaction. Nothing here suggests acute danger, but the safety file is thin, old, and drawn from a drug that fell out of use.

Safety at a Glance

⚠️ Moderate toxicityDrug interactions

• No serious toxicity signal in the trial record. The 1978 comparison against nicergoline reported no adverse effects, and animal work has not flagged organ toxicity at the doses studied ^{7Reference 7Marolda M et al. · 1978Clinical trialClinical evaluation of (-)eburnamonine in comparison with nicergoline in patients suffering from chronic brain ischemia — clinical trialView study →}.
• Dose-dependent gastrointestinal effects. The higher regimen (3 × 60 mg/day) produced more gastrointestinal side effects than 1 × 60 mg/day in the placebo-controlled trial ^{8Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →}.
• Lymphocytic colitis has been attributed to vinburnine. A case report and a subsequent drug-induced-enterocolitis review name it among the drugs associated with microscopic colitis ^{28,29Reference 28Chauveau E et al. · 1998Case reportChauveau E, et al. (1998). [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)] — case report. Gastroentérologie Clinique et Biologique. https://pubmed.ncbi.nlm.nih.gov/9762227/View study →Reference 29Tysk C · 2000ReviewTysk C (2000). [Drug-induced enterocolitis. Important differential diagnosis in the investigation of diarrhea and intestinal hemorrhage] — review. Läkartidningen. https://pubmed.ncbi.nlm.nih.gov/10881520/View study →}.
• Cutaneous drug reaction. A bullous fixed drug eruption induced by vinburnine has been reported ^{37Reference 37Schena D et al. · 1992Case reportBullous fixed drug eruption induced by vinburnine — case reportView study →}.
• Vasoactive and cardiac-adjacent. It is a cerebral vasoactive agent with M2-preferring muscarinic allosteric activity, so caution is reasonable with antihypertensives, other vasodilators and cardiac medication — though no formal interaction study exists ^{12,13Reference 12Proska J et al. · 1996Positive allosteric action of eburnamonine on cardiac muscarinic acetylcholine receptorsView study →Reference 13Maksay G et al. · 2004Vinburnine decelerates [3H]N-methylscopolamine binding to recombinant human muscarinic M1-M4 acetylcholine receptorsView study →}.

Full Safety and Interactions Detail

Gastrointestinal. The clearest dose-related effect. In the two-dose placebo-controlled study, therapeutic improvement was greater at 3 × 60 mg/day than at 1 × 60 mg/day, but so were gastrointestinal side effects ^{8Reference 8Jansen W et al. · 1986Clinical trialExperimental clinical studies on the effect of eburnamonine in cerebrovascular disorders — clinical trialView study →}. More seriously, lymphocytic colitis was attributed to vinburnine (Cervoxan) in a French case report ^{28Reference 28Chauveau E et al. · 1998Case reportChauveau E, et al. (1998). [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)] — case report. Gastroentérologie Clinique et Biologique. https://pubmed.ncbi.nlm.nih.gov/9762227/View study →}, and vinburnine subsequently appears in a review of drug-induced enterocolitis as an agent associated with microscopic colitis presenting with diarrhoea ^{29Reference 29Tysk C · 2000ReviewTysk C (2000). [Drug-induced enterocolitis. Important differential diagnosis in the investigation of diarrhea and intestinal hemorrhage] — review. Läkartidningen. https://pubmed.ncbi.nlm.nih.gov/10881520/View study →}. Microscopic colitis is a recognised drug-attributable syndrome and is easy to miss; anyone with unexplained watery diarrhoea on an alkaloid of this class should have it considered.

Skin. A bullous fixed drug eruption induced by vinburnine has been documented ^{37Reference 37Schena D et al. · 1992Case reportBullous fixed drug eruption induced by vinburnine — case reportView study →}. Fixed drug eruption is idiosyncratic and recurs at the same site on re-exposure.

Cardiovascular and interaction scope. Eburnamonine is a positive allosteric modulator of muscarinic receptors with its highest potency at the cardiac M2 subtype (EC50 4.1 µM) ^{13Reference 13Maksay G et al. · 2004Vinburnine decelerates [3H]N-methylscopolamine binding to recombinant human muscarinic M1-M4 acetylcholine receptorsView study →}, and the effect was originally characterised on cardiac muscarinic receptors ^{12Reference 12Proska J et al. · 1996Positive allosteric action of eburnamonine on cardiac muscarinic acetylcholine receptorsView study →}. Whether that translates into any cardiac effect at achievable plasma concentrations is unknown, but it is the most concrete theoretical interaction concern here. As a cerebral vasoactive agent it plausibly stacks with antihypertensives and other vasodilators. No CYP-isoform inhibition or induction data, no transporter-inhibition data beyond the P-gp/BCRP substrate assay, and no formal drug-interaction study were located — do not read that silence as safety ^{10Reference 10Fandy TE et al. · 2016In vitroIn vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonineView study →}.

Populations and scope. No paediatric, renal-impairment or hepatic-impairment data were identified. No reproductive or developmental toxicity dataset exists for eburnamonine. It is worth stating explicitly that the FDA’s developmental-toxicity warning applies to vinpocetine — a different, semi-synthetic molecule — and has not been shown for eburnamonine; the absence of a finding here reflects the absence of a study, not a clean result. Pregnancy and lactation decisions belong to the herb or product page where intake is actually decided.

Dosage

There is no established dose for eburnamonine as a plant constituent, and no supplement standardised to it. The figures below are the historic pharmaceutical doses of vinburnine recorded in the European studies, given so the human data here can be read in proportion.

For scale: Vinca minor leaf macerate contained vincamine — the plant’s most abundant alkaloid — at 2.459 mg/100 g dry weight, with eburnamonine present at a lower, unquantified level ^{21Reference 21Neculai AM et al. · 2023Determination of active ingredients, mineral composition and antioxidant properties of hydroalcoholic macerates of Vinca minor L. plant from the Dobrogea areaView study →}. A herbal preparation therefore delivers on the order of micrograms to a fraction of a milligram of this molecule, against a drug dose of 60 mg or more. These are doses studied in research and prescribed historically; they are not a personal recommendation, and vinburnine is no longer a current therapy.

References

1. Bartlett MF, Taylor WI (1960). The Alkaloids of Hunteria eburnea. I. The Structures of Eburnamine, Isoburnamine, Eburnamenine and Eburnamonine and a Synthesis of rac-Eburnamonine. Journal of the American Chemical Society 82(22):5941–5946. https://doi.org/10.1021/ja01507a036
2. Linée P, et al. (1978). Cerebral metabolic, hemodynamic and antihypoxic properties of l-eburnamonine. European Neurology. https://pubmed.ncbi.nlm.nih.gov/753626/
3. Villa RF, et al. (1978). Effect of (-)eburnamonine, papaverine and UDP-glucose on cerebral energy state during and after experimental hypoxia and ischaemia in beagle dog. European Neurology. https://pubmed.ncbi.nlm.nih.gov/753643/
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