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361-37-5 molecular structure
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(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

ChemBase ID: 132
Molecular Formular: C21H27N3O2
Molecular Mass: 353.45798
Monoisotopic Mass: 353.21032712
SMILES and InChIs

SMILES:
O=C(N[C@@H](CC)CO)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)cn(c3ccc1)C)C
Canonical SMILES:
CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
InChI:
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
InChIKey:
KPJZHOPZRAFDTN-ZRGWGRIASA-N

Cite this record

CBID:132 http://www.chembase.cn/molecule-132.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
IUPAC Traditional name
methysergide
Brand Name
Deseril
Desernil
Desernyl
Deseryl
Sansert
Synonyms
Methyllysergic acid butanolamide
Methysergid
Methysergidum [INN-Latin]
Metisergide [DCIT]
Metisergido [INN-Spanish]
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide
Methysergide
CAS Number
361-37-5
PubChem SID
160963595
PubChem CID
9681
ATC CODE
N02CA04
CHEMBL
1065
Chemspider ID
9300
DrugBank ID
DB00247
IUPHAR ligand ID
134
KEGG ID
D02357
Unique Ingredient Identifier
XZA9HY6Z98
Wikipedia Title
Methysergide
Medline Plus
a603022

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.006512  H Acceptors
H Donor LogD (pH = 5.5) -0.5095057 
LogD (pH = 7.4) 1.2321609  Log P 1.8168944 
Molar Refractivity 104.4726 cm3 Polarizability 41.054924 Å3
Polar Surface Area 57.5 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.22  LOG S -3.2 
Solubility (Water) 2.24e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Hydrophobicity(logP)
1.5 expand Show data source
Pregnancy Category
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DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00247 external link
Item Information
Drug Groups approved
Description An ergot derivative that is a congener of lysergic acid diethylamide. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome. [PubChem]
Indication For the treatment of vascular headache
Pharmacology Methysergide has been shown, in vitro and in vivo, to inhibit or block the effects of serotonin, a substance which may be involved in the mechanism of vascular headaches. Serotonin has been variously described as a central neurohumoral agent or chemical mediator, as a "headache substance" acting directly or indirectly to lower pain threshold, as an intrinsic "motor hormone" of the gastrointestinal tract, and as a "hormone" involved in connective tissue reparative processes.
Toxicity Few cases of acute methysergide intoxication have been reported. The possible symptom complex is therefore not fully known. The following symptoms are based on these few case reports. Euphoria, hyperactivity, tachycardia, dilated pupils, and dizziness have been reported in a child with a dose of 20-24 mg of methysergide. In adults, peripheral vasospasm, with diminished or absent pulses, coldness, mottling and cyanosis, has been observed at a dose of 200 mg. Ischemic tissue damage has not been reported in acute overdosage with methysergide.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Rapid
External Links
Wikipedia
RxList

REFERENCES

REFERENCES

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PATENTS

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