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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:38 UTC
HMDB IDHMDB0014497
Secondary Accession Numbers
  • HMDB14497
Metabolite Identification
Common NameMethylergonovine
DescriptionMethylergonovine, also known as ergotyl or methylergobasin, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Its specific binding and activation pattern on these receptors leads to a highly, if not completely, specific contraction of smooth uterus muscle via 5-HT2A serotonin receptors, while blood vessels are affected to a lesser extent compared to other ergot alkaloids. Due to its oxytocic properties, it has a medical use in obstetrics. It is available as tablets or injection (IM or IV) or in liquid form to be taken orally. Methylergonovine is a drug which is used for the prevention and control of excessive bleeding following vaginal childbirth. It is also contraindicated in HIV positive patients taking protease inhibitors, delavirdine and efavirenz (which is also an agonist at the 5HT2A-mGlu2 receptor protomer and increases the chances of a patient experiencing hallucinations during methylergometrine therapy). Methylergometrine (also called methylergonovine, methylergobasin, and D-lysergic acid 1-butanolamide) is a synthetic analogue of ergometrine, a psychedelic alkaloid found in ergot, and many species of morning glory. Methylergonovine is a very strong basic compound (based on its pKa). Methylergonovine is a potentially toxic compound. It can also increase constriction of blood vessels caused by sympathomimetic drugs and other ergot alkaloids. Methylergometrine likely interacts with drugs that inhibit the liver enzyme CYP3A4, such as azole antifungals, macrolide antibiotics and many HIV drugs. Methylergometrine maleate is marketed under the trade name Methergine.
Structure
Data?1582753186
Synonyms
ValueSource
ErgotylKegg
MethylergobasinHMDB
MethylergobasineHMDB
MethylergobrevinHMDB
MethylergometrinHMDB
MethylergometrineHMDB
MethylergonovinHMDB
Methylergonovine maleateHMDB
Novartis brand OF methylergonovine maleateHMDB
MétherginHMDB
MetherginHMDB
MethergineHMDB
Methylergometrine maleateHMDB
MethylergonovineMeSH
Chemical FormulaC20H25N3O2
Average Molecular Weight339.4314
Monoisotopic Molecular Weight339.194677059
IUPAC Name(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional Namemethylergonovine
CAS Registry Number113-42-8
SMILES
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO
InChI Identifier
InChI=1S/C20H25N3O2/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/t13-,14+,18-/m1/s1
InChI KeyUNBRKDKAWYKMIV-QWQRMKEZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergamides
Alternative Parents
Substituents
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline-3-carboxamide
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 g/LNot Available
LogP1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.74ALOGPS
logP1.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)7.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area68.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.58 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.08131661259
DarkChem[M-H]-177.97431661259
DeepCCS[M-2H]-217.15830932474
DeepCCS[M+Na]+192.19930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methylergonovine[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO4696.4Standard polar33892256
Methylergonovine[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO3426.4Standard non polar33892256
Methylergonovine[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO3503.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylergonovine,1TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C13071.4Semi standard non polar33892256
Methylergonovine,1TMS,isomer #2CC[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C13088.2Semi standard non polar33892256
Methylergonovine,1TMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C3020.8Semi standard non polar33892256
Methylergonovine,2TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C3039.4Semi standard non polar33892256
Methylergonovine,2TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C3286.9Standard non polar33892256
Methylergonovine,2TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C4010.4Standard polar33892256
Methylergonovine,2TMS,isomer #2CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C13016.9Semi standard non polar33892256
Methylergonovine,2TMS,isomer #2CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C13243.2Standard non polar33892256
Methylergonovine,2TMS,isomer #2CC[C@@H](CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C13951.0Standard polar33892256
Methylergonovine,2TMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C2995.8Semi standard non polar33892256
Methylergonovine,2TMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C3245.0Standard non polar33892256
Methylergonovine,2TMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C4002.6Standard polar33892256
Methylergonovine,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C3036.6Semi standard non polar33892256
Methylergonovine,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C3272.9Standard non polar33892256
Methylergonovine,3TMS,isomer #1CC[C@@H](CO[Si](C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C3762.7Standard polar33892256
Methylergonovine,1TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C13303.9Semi standard non polar33892256
Methylergonovine,1TBDMS,isomer #2CC[C@@H](CO)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C13290.6Semi standard non polar33892256
Methylergonovine,1TBDMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3251.7Semi standard non polar33892256
Methylergonovine,2TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3460.5Semi standard non polar33892256
Methylergonovine,2TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3753.4Standard non polar33892256
Methylergonovine,2TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=C[NH]4)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C4096.3Standard polar33892256
Methylergonovine,2TBDMS,isomer #2CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C13432.3Semi standard non polar33892256
Methylergonovine,2TBDMS,isomer #2CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C13672.9Standard non polar33892256
Methylergonovine,2TBDMS,isomer #2CC[C@@H](CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C14060.2Standard polar33892256
Methylergonovine,2TBDMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3407.6Semi standard non polar33892256
Methylergonovine,2TBDMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3700.6Standard non polar33892256
Methylergonovine,2TBDMS,isomer #3CC[C@@H](CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C4078.6Standard polar33892256
Methylergonovine,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3610.0Semi standard non polar33892256
Methylergonovine,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3915.1Standard non polar33892256
Methylergonovine,3TBDMS,isomer #1CC[C@@H](CO[Si](C)(C)C(C)(C)C)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4[Si](C)(C)C(C)(C)C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3914.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylergonovine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3914000000-d6349f005e32538214212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylergonovine GC-MS (1 TMS) - 70eV, Positivesplash10-01ba-4095000000-07cac91c483c45e0b4fc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylergonovine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 10V, Positive-QTOFsplash10-006x-1019000000-5743eb114639a8b4cd682016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 20V, Positive-QTOFsplash10-0uk9-4093000000-2f215482a3bef9973b4f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 40V, Positive-QTOFsplash10-00di-3940000000-bf7ef321bb426974d49b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 10V, Negative-QTOFsplash10-000i-0019000000-25ad156f1bdbadfdb37f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 20V, Negative-QTOFsplash10-05g0-2169000000-04eae81fd7d7bb4dbf722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 40V, Negative-QTOFsplash10-05fu-8290000000-0f17abb269c859d8cdac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 10V, Positive-QTOFsplash10-0006-0019000000-011f8e744770762714122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 20V, Positive-QTOFsplash10-006x-1069000000-38039c479f71c2219d4d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 40V, Positive-QTOFsplash10-00di-0190000000-68a0ea065cbe0f2aeef02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 10V, Negative-QTOFsplash10-000i-0009000000-7d83f1b1716bd17dabc82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 20V, Negative-QTOFsplash10-000i-0009000000-4856ff7ce1f702c342f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylergonovine 40V, Negative-QTOFsplash10-0avl-5290000000-bb401d09f7282c1260d22021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00353 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00353 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00353
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7933
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylergometrine
METLIN IDNot Available
PubChem Compound8226
PDB IDNot Available
ChEBI ID775307
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [PubMed:12583687 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Reyes FD, Mozzachiodi R, Baxter DA, Byrne JH: Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20. [PubMed:15930499 ]
  4. Nargeot R, Baxter DA, Patterson GW, Byrne JH: Dopaminergic synapses mediate neuronal changes in an analogue of operant conditioning. J Neurophysiol. 1999 Apr;81(4):1983-7. [PubMed:10200235 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]