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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:15:58 UTC
HMDB IDHMDB0014392
Secondary Accession Numbers
  • HMDB14392
Metabolite Identification
Common NameMethysergide
DescriptionMethysergide, also known as metisergida, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Methysergide is a drug which is used for the treatment of vascular headache. A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches. Methysergide is a very strong basic compound (based on its pKa). Methysergide is a potentially toxic compound.
Structure
Data?1582753174
Synonyms
ValueSource
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamideChEBI
(+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamideChEBI
1-Methyl-D-lysergic acid butanolamideChEBI
1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamideChEBI
1-Methyllysergic acid butanolamideChEBI
1-MethylmethylergonovineChEBI
9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamideChEBI
MethysergidumChEBI
MetisergidaChEBI
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamideChEBI
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8b-carboxamideGenerator
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-carboxamideGenerator
1-Methyl-D-lysergate butanolamideGenerator
1-Methyl-dextro-lysergate (+)-1-hydroxy-2-butylamideGenerator
1-Methyllysergate butanolamideGenerator
Methyllysergic acid butanolamideHMDB
MethysergidHMDB
MetisergideHMDB
N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamideHMDB
1-Methyllysergic acid butanolamide tartrate, (R-(r*,r*))-(8beta)-isomerHMDB
Chemical FormulaC21H27N3O2
Average Molecular Weight353.458
Monoisotopic Molecular Weight353.210327123
IUPAC Name(4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
Traditional Namemethysergide
CAS Registry Number361-37-5
SMILES
[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO
InChI Identifier
InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1
InChI KeyKPJZHOPZRAFDTN-NQUBZZJWSA-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
  • N-alkylindole
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • N-methylpyrrole
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Carboxamide group
  • Amino acid or derivatives
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point195 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 g/LNot Available
LogP1.5Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP10(2.22) g/LALOGPS
logP10(1.82) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)7.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.47 m³·mol⁻¹ChemAxon
Polarizability40.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.81131661259
DarkChem[M-H]-178.37531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methysergide,1TMS,#1CCC(CO[Si](C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C12997.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Methysergide,1TMS,#2CCC(CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C2995.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Methysergide,1TBDMS,#1CCC(CO[Si](C)(C)C(C)(C)C)NC(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C13239.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Methysergide,1TBDMS,#2CCC(CO)N(C(=O)[C@@H]1C=C2C3=CC=CC4=C3C(=CN4C)C[C@H]2N(C)C1)[Si](C)(C)C(C)(C)C3206.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methysergide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4495000000-d0cc0e065ac2a249f1392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methysergide GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3390100000-c2e2183c67e221dc8c1d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methysergide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methysergide 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 - Methysergide 10V, Positive-QTOFsplash10-0udr-1009000000-633c43ec26d6039658e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 20V, Positive-QTOFsplash10-00kr-5095000000-47b5108f6a3ebd9492362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 40V, Positive-QTOFsplash10-0c0c-3390000000-7d1562a443e084f1ea992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 10V, Negative-QTOFsplash10-0udi-0009000000-9ba72bc3d8d89f6a43882016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 20V, Negative-QTOFsplash10-0ff9-2059000000-819b11151769bcbb64452016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 40V, Negative-QTOFsplash10-05g3-6090000000-5d7ac6f788f61ce269292016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 10V, Positive-QTOFsplash10-0udi-0019000000-5a70e47475b13679f8e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 20V, Positive-QTOFsplash10-0udr-0059000000-d42a975e818a2288348e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 40V, Positive-QTOFsplash10-000i-0090000000-22d20459936ae0d0b5182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 10V, Negative-QTOFsplash10-0udi-0009000000-c66b7fea4f08e0ca5b512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 20V, Negative-QTOFsplash10-0udi-1019000000-b7eebee23bde51802f582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methysergide 40V, Negative-QTOFsplash10-0kfx-6193000000-c592c6e25521a17d47402021-09-22Wishart 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 DB00247 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00247 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 IDDB00247
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5022813
KEGG Compound IDC07199
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethysergide
METLIN IDNot Available
PubChem Compound6540428
PDB IDNot Available
ChEBI ID584020
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 G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4
References
  1. Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
References
  1. Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H: Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache? Eur J Neurosci. 1996 May;8(5):959-67. [PubMed:8743744 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Scrogin KE, Johnson AK, Brooks VL: Methysergide delays the decompensatory responses to severe hemorrhage by activating 5-HT(1A) receptors. Am J Physiol Regul Integr Comp Physiol. 2000 Nov;279(5):R1776-86. [PubMed:11049861 ]
  2. Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155 ]
  3. Sugimoto Y, Inoue K, Yamada J: Involvement of 5-HT(2) receptor in imipramine-induced hyperglycemia in mice. Horm Metab Res. 2003 Sep;35(9):511-6. [PubMed:14517765 ]
  4. Skyba DA, Radhakrishnan R, Rohlwing JJ, Wright A, Sluka KA: Joint manipulation reduces hyperalgesia by activation of monoamine receptors but not opioid or GABA receptors in the spinal cord. Pain. 2003 Nov;106(1-2):159-68. [PubMed:14581123 ]
  5. Pranzatelli MR, Balletti J: Characterization of 5-hydroxytryptamine 1A-like binding sites in human ganglioneuroblastoma. Neurosci Lett. 1991 Oct 28;132(1):117-20. [PubMed:1838579 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Castilho VM, Avanzi V, Brandao ML: Antinociception elicited by aversive stimulation of the inferior colliculus. Pharmacol Biochem Behav. 1999 Mar;62(3):425-31. [PubMed:10080233 ]
  2. Geerts IS, Matthys KE, Herman AG, Bult H: Involvement of 5-HT1B receptors in collar-induced hypersensitivity to 5-hydroxytryptamine of the rabbit carotid artery. Br J Pharmacol. 1999 Jul;127(6):1327-36. [PubMed:10455282 ]
  3. Shaw AM, Brown C, Irvine J, Bunton DC, MacDonald A: Role of the 5-HT(2A)receptor and alpha(1)-adrenoceptor in the contractile response of rat pulmonary artery to 5-HT in the presence and absence of nitric oxide. Pulm Pharmacol Ther. 2000;13(6):277-85. [PubMed:11061982 ]
  4. Prins NH, Akkermans LM, Lefebvre RA, Schuurkes JA: Characterization of the receptors involved in the 5-HT-induced excitation of canine antral longitudinal muscle. Br J Pharmacol. 2001 Nov;134(6):1351-9. [PubMed:11704657 ]
  5. Connor JD, Rasheed H, Gilani AH, Cheema M, Rizvi Z, Saeed SA: Second messengers in platelet aggregation evoked by serotonin and A23187, a calcium ionophore. Life Sci. 2001 Oct 26;69(23):2759-64. [PubMed:11720080 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Johnson MP, Lea RA, Curtain RP, MacMillan JC, Griffiths LR: An investigation of the 5-HT2C receptor gene as a migraine candidate gene. Am J Med Genet B Neuropsychiatr Genet. 2003 Feb;117B(1):86-9. [PubMed:12555241 ]