Skip to content
PsychedeliaDokholyan Laboratory
Plate 413 of 545Verified

Methergine

Also known asMethylergonovine maleate · Maleic acid, methyl ergonovine · Methylergonovine maleate (USP) · Methylergonovine maleate [USP] · Methylergometrine maleate · Methyl Ergonovine Maleate Salt · Methylergometrine (maleate) · Erezingen

(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid

PubChem CID
5281072
Measurements
12
InChIKey
NOFOWWRHEPHDCY-DAUURJMHSA-N

I · Summary

What is known

Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.

What it is

  • Methylergonovine Maleate is an ergoline alkaloid. It has a role as a geroprotector.

    ChEBI

  • Methylergonovine Maleate is the maleate salt of methylergonovine, a semi-synthetic ergot alkaloid with vasoconstrictive and uterotonic effects. Methylergonovine stimulates serotoninergic and dopaminergic receptors as well as inhibits the release of endothelial-derived relaxation factor. This results in arterial vasoconstriction and increased uterine smooth muscle contractions.

    NCI Thesaurus (NCIt)

  • Methylergonovine is only found in individuals that have used or taken this drug. It is a homolog of ergonovine containing one more CH2 group (Merck Index, 11th ed). Methylergonovine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions through binding and the resultant antagonism of the dopamine D1 receptor. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss.

    Toxin and Toxin Target Database (T3DB)

Recognized use

  • Methylergometrine is a synthetic analogue of ergonovine, an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi like other ergoline alkaloids. Methylergometrine is a blood vessel constrictor and smooth muscle agonist most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. It also causes uterine contractions to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. The drug is currently prepar…

    Toxin and Toxin Target Database (T3DB)

How it acts

    Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.

    In the body

    • Hepatic, with extensive first-pass metabolism. Route of Elimination: Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver. Half Life: 3.39 hours

      Toxin and Toxin Target Database (T3DB)

    History, discovery and cultural use

    — Not in this archive. PubChem, ChEMBL and the Human Protein Atlas publish pharmacology, regulation and toxicology, and none of them publishes a heading for when Methergine was first made, by whom, or how it has been used. That is a gap in the databases this site reads and not a gap in the literature — the history of these compounds is written, at length and under peer review, in the works below. This site does not summarize them; it says where they are. Where a published passage above happens to touch origin or traditional use, it appears inside the entry that carries it.

    Histories of this field

    Scholarship on psychedelics generally, not on Methergine specifically. Whether any of these treats this compound is a question for the book, not for this page.

    • Mescaline: A Global History of the First Psychedelic

      Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.

      Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.

    • Expanding Mindscapes: A Global History of Psychedelicsopen access

      Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.

      Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.

    • Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers

      Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.

      Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.

    • Psychonauts: Drugs and the Making of the Modern Mind

      The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.

      Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.

    • Ancient Psychoactive Substances

      Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.

      Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.

    • History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders

      A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.

      Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.

      Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.

    • Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions

      Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.

      Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.

    Institutional archives

    • Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
    • Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.

    The rest of this dossier

    • Affinity — 12 measurements in this archive, equilibrium constants kept apart from functional readouts.
    • Toxicology — 1 published passage, plus any assay in this archive bearing on toxicity.
    • Legal — no DEA record is held here — which is not a finding that this compound is uncontrolled.
    • Systems — where this compound’s targets are transcribed, by brain region and tissue.

    Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about Methergine is the history note, which says so on its face and carries a reference for every claim in it.

    II · Identity

    Structure and descriptors

    Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.

    2D structural depiction of Methergine
    Depiction served by PubChem for CID 5281072. Not redrawn here, so the picture and the identity come from the same record.
    Formula
    C24H29N3O6R
    Molecular weight
    455.51g/molR
    Exact mass
    455.2056DaR
    cLogP
    1.64R
    TPSA
    143.0ŲR
    H-bond donors
    5R
    H-bond acceptors
    5R
    Rotatable bonds
    6R
    Aromatic rings
    2R
    Heavy atoms
    33R
    Fraction sp³
    0.375R
    Formal charge
    0R

    Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.

    Bemis–Murcko scaffold

    C1=C2c3cccc4[nH]cc(c34)C[C@H]2NCC1

    Shared with 1B-LSD, 1DD-LSD, 1H-LSD, 1P-AL-LAD, 1P-ETH-LAD, 1P-LSD and 23 more. All families

    III · Behavior

    Behavioral summary

    Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.

    Classification

    Duration of acute subjective effects

    —

    No controlled human trial reporting a duration for this compound is cited here. The archive holds no other record of one either. A duration is not inferred from a chemical relative.

    Plasma elimination half-life

    How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.

    No half-life is published for this compound in the sources this site reads.

    Primary pharmacological drivers

    IV · Clinical

    Clinical description

    Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.

    No diagnostic chapter is shown for this compound. Either PubChem records no MeSH pharmacological class for it, or the class it records is not one of the substance classes ICD-11 gives a chapter to. Inferring a chapter from the compound’s name or its binding profile would be a diagnosis this archive is in no position to make.

    How much has been written about each domain

    The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.

    Affect0Mood0Perception1Cognition0Thought process0Thought content0Psychomotor activity0Insight and judgment0
    This measures the literature, not the compound. Each spoke counts how many of the 1 records this archive holds for this compound say something under that domain — 1 at the widest ring. A long spoke means the subject has been written about, not that the effect is strong, and a spoke at the center means nothing here discusses it rather than that nothing happens. The terms behind each domain are listed in the method.
    Perception 1
    matched on “hallucinat” · in Toxicology: Toxin and Toxin Target Database (T3DB)

    V · Systems

    Systems physiology

    Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.

    Brain

    cerebral cortex — 18.2 nTPM, from HTR2A, HTR1A, HTR2Ccerebellum — 0.2 nTPM, from HTR2A, HTR1Bhippocampal formation — 6.1 nTPM, from HTR1A, HTR2A, HTR2Camygdala — 3.5 nTPM, from HTR2A, HTR2C, HTR1Ahypothalamus — 12.6 nTPM, from HTR2C, HTR2A, HTR1Athalamus — no resolved target expressed herebasal ganglia — 28.2 nTPM, from HTR2C, HTR2A, HTR1Bmedulla oblongata — no resolved target expressed here

    basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.

    Measured but not drawn — this anatomogram has no outline for them: midbrain 2.2, spinal cord 1.0, retina 0.7, pituitary gland 0.4.

    Body

    heart — 0.7 nTPM, from HTR2A, HTR1Asmooth muscle — 2.4 nTPM, from HTR2A, HTR1Blung — 0.3 nTPM, from HTR2A, HTR1Bliver — 0.1 nTPM, from HTR2Akidney — 0.3 nTPM, from HTR1B, HTR2Astomach — 4.7 nTPM, from HTR1B, HTR2Aduodenum — 0.4 nTPM, from HTR2A, HTR1Bsmall intestine — 0.4 nTPM, from HTR2A, HTR1Bcolon — 0.5 nTPM, from HTR2A, HTR1Badrenal gland — 0.5 nTPM, from HTR1B, HTR2Athyroid gland — 0.1 nTPM, from HTR2A, HTR1Bpancreas — 0.1 nTPM, from HTR1Burinary bladder — 1.0 nTPM, from HTR1B, HTR2Askeletal muscle — 0.3 nTPM, from HTR2Aspleen — no resolved target expressed heresalivary gland — 0.2 nTPM, from HTR1B, HTR2A
    028 nTPM

    Square-root ramp · shared scale across both plates

    Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.

    Brain regions

    Regions where this compound's measured targets are transcribed. Linked from the plate above.

    1. basal ganglia

      28.2 nTPM

    2. cerebral cortex

      18.2 nTPM

    3. hypothalamus

      12.6 nTPM

    4. hippocampal formation

      6.1 nTPM

    5. amygdala

      3.5 nTPM

    6. midbrain

      2.2 nTPM

    7. spinal cord

      1.0 nTPM

    8. retina

      0.7 nTPM

    9. pituitary gland

      0.4 nTPM

    10. cerebellum

      0.2 nTPM

    Peripheral & autonomic

    Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.

    1. stomach 1

      4.7 nTPM

    2. smooth muscle

      2.4 nTPM

    3. urinary bladder

      1.0 nTPM

    4. heart muscle

      0.7 nTPM

    5. colon

      0.5 nTPM

    6. adrenal gland

      0.5 nTPM

    7. duodenum

      0.4 nTPM

    8. small intestine

      0.4 nTPM

    9. lung

      0.3 nTPM

    10. skeletal muscle

      0.3 nTPM

    11. kidney

      0.3 nTPM

    12. salivary gland

      0.2 nTPM

    13. liver

      0.1 nTPM

    14. thyroid gland

      0.1 nTPM

    15. pancreas

      0.1 nTPM

    Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.

    Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.

    VI · Profile

    Affinity rosette

    The strongest measurement at each of 4 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.

    5-HT2A — Ki 8.96 pX5-HT1A — Ki 8.82 pX5-HT2C — Ki 7.69 pX5-HT1B — Ki 6.60 pX5-HT2A5-HT1A5-HT2C5-HT1B579
    Fig. Radius is pX = −log₁₀(value in M), that is 9 − log₁₀(value in nM), computed from the normalized measurement. Hatched wedges are equilibrium binding constants (Ki, Kd); dashed outlines are functional readouts (IC₅₀, EC₅₀, AC₅₀, potency), which answer a different question and are not pooled with them. Rings mark whole pX units from 5 to 10, labeled every second ring in the gutter at the top. Where a target carries several measurements, the strongest is drawn.

    VII · Toxicology

    Toxicological profile

    What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.

    Measured in this archive

    Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.

    No hERG, cytochrome, cytotoxicity or transport measurement exists for Methergine in this archive.

    As published

    Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.

    Toxicity Summary

    • Ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. (A2914, A2915, A2916)

      Toxin and Toxin Target Database (T3DB)

    Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.

    VIII · Evidence

    Every measurement

    One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.

    Equilibrium binding constants 11

    Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.

    TargetClassTypeValue (nM)pXOrganismAssay
    5-HT2ASerotonin receptorsKi1.108.96HUMANPDSP
    5-HT2ASerotonin receptorsKi1.418.85PIGPDSP
    5-HT1ASerotonin receptorsKi1.508.82HUMANPDSP
    5-HT1ASerotonin receptorsKi1.988.70HUMANPDSP
    5-HT1ASerotonin receptorsKi4.008.40PIGPDSP
    5-HT2CSerotonin receptorsKi20.407.69PIGPDSP
    5-HT2CSerotonin receptorsKi24.507.61PIGPDSP
    5-HT2CSerotonin receptorsKi25.107.60PIGPDSP
    5-HT2CSerotonin receptorsKi43.707.36HUMANPDSP
    5-HT2CSerotonin receptorsKi46.807.33PIGPDSP
    5-HT1BSerotonin receptorsKi2516.60RATPDSP

    Functional readouts 1

    IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.

    TargetClassTypeValue (nM)pXOrganismAssay
    Caspase-6UnclassifiedAC507,0405.15Homo sapiensCHEMBL3214833
    P
    PubChem
    C
    ChEMBL
    R
    Computed here with RDKit
    D
    Derived here from the stored measurement

    IX · Trials

    Registered clinical trials

    Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.

    4T

    Registered studies

    0T

    Open or ongoing

    4T

    With a phase recorded

    By phase

    A study may carry two phase codes at once, so these count studies bearing each phase and do not sum to the total.

    • Phase 11
    • Phase 42
    • Not applicable1

    By status

    The registry’s own status for each record. Withdrawn and terminated studies are counted here rather than hidden — a stopped trial is part of what is known.

    • Completed4

    Every matched study

    Newest first by start date. Each identifier opens the registry record it came from; the title is the sponsor’s own, quoted.

    • NCT03584854Completed · Phase 4

      Second-Line Uterotonics in Postpartum Hemorrhage: A Randomized Clinical Trial

      Enrollment
      100Tactual
      Started
      2019-03-01
      Sponsor
      Brigham and Women's Hospital

      Conditions Postpartum Hemorrhage · Uterine Atony

      Matched “Methylergonovine maleate” in the study’s intervention “Methylergonovine Maleate”

    • NCT03390010Completed · Phase 1

      Misoprostol Versus Active Management of Labour in CS

      Enrollment
      300Tactual
      Started
      2017-12-28
      Sponsor
      Aljazeera Hospital

      Conditions Cesarean Section

      Matched “Methergine” in the study’s intervention “Misoprostol + syntocinon and using extra uterotonic drugs when needed ; methergine”

    • NCT02408965Completed · Phase 4

      Uterotonic Prophylaxis Trial

      Enrollment
      284Tactual
      Started
      2015-03
      Sponsor
      University of California, San Francisco

      Conditions Hemorrhage

      Matched “Methergine” in the study’s intervention “Methergine”

    • NCT00858832Completed · Not applicable

      Reduction of Endometritis After Cesarean Section With the Routine Use of Methergine

      Enrollment
      44Tactual
      Started
      2008-12
      Sponsor
      University of South Florida

      Conditions Endometritis

      Matched “Methergine” in the study’s intervention “Methergine”

    Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.

    Searched as Methergine · Methylergonovine maleate · Maleic acid, methyl ergonovine. Run this search at the registry — it returns the unfiltered result, including studies this page rejected as belonging to a different molecule.

    A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether Methergine worked.

    XI · Literature

    Sources behind this dossier

    The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.

    No reference is recorded against any value for this compound. Its measurements come from ChEMBL assay records that carry an assay identifier but no publication, so there is no paper to cite here — an absence in the upstream record, not a judgment about the evidence. The assay identifiers in Every measurement resolve to the records the values were read from.