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Name	Methysergide dimaleate	EINECS	204-950-9
CAS No.	129-49-7	Density	1.28g/cm³
PSA	132.10000	LogP	1.97570
Solubility	DMSO: >10 mg/mL	Melting Point	N/A
Formula	C₂₁H₂₇N₃O₂•C₄H₄O₄	Boiling Point	634.4 °C at 760 mmHg
Molecular Weight	469.538	Flash Point	337.5 °C
Transport Information	UN 2811 6	Appearance	white to off-white
Safety	Poison by ingestion and intravenous routes. Experimental reproductive effects. Human mutation effects reported. When heated to decomposition it emits toxic fumes of NO_x.	Risk Codes	25
Molecular Structure		Hazard Symbols	T
Synonyms	1-(hydroxymethyl)propylamideof1-methyl-(+)-lysergicacidhydrogenmaleate;deseril-retard;ergoline-8-beta-carboxamide,9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dim;maleate(1:1)(salt);methysergidebimaleate;methysergidedimaleate;methysergidehydrogenmaleate;n-((1-hydroxymethyl)propyl)-1-methyl-lysergamidmaleate

Methysergide dimaleate Synthetic route

: 129-49-7
methysergide maleate

: (6aR,9R,10aR)-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 3750.38 Torr; Autoclave;	85%

: 129-49-7
methysergide maleate

: 1615738-02-7
(6aR,9R)-5-bromo-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions

Conditions	Yield
Stage #1: methysergide maleate With sodium hydrogencarbonate In dichloromethane Stage #2: With trimethylsilyl bromide In dimethyl sulfoxide at 20℃; for 0.166667h;	73%
With trimethylsilyl bromide In dimethyl sulfoxide at 20℃; for 0.166667h;

: 67-56-1
methanol

: 129-49-7
methysergide maleate

: (6aR,9R,10aS)-N-((S)-1-hydroxybutan-2-yl)-10a-methoxy-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions

Conditions	Yield
With sulfuric acid at -20℃; for 2h; Inert atmosphere; Irradiation;	12%

: 129-49-7
methysergide maleate

: (6aR,9R,10aR)-5-bromo-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C / 3750.38 Torr / Autoclave 2: trimethylsilyl bromide / dimethyl sulfoxide / 0.17 h / 20 °C View Scheme

: 129-49-7
methysergide maleate

: (6aR,9R,10aR)-5-cyclopropyl-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C / 3750.38 Torr / Autoclave 2: trimethylsilyl bromide / dimethyl sulfoxide / 0.17 h / 20 °C 3: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; water / 90 °C View Scheme

Methysergide dimaleate Chemical Properties

Product Name: Methysergide dimaleate
Synonyms of Methysergide dimaleate (CAS NO.129-49-7): Methysergide ; Methysergide maleate [USAN] ; (+)-N-((1-Hydroxymethyl)propyl)-1-methyl-D-lysergamide bimaleate ; 1-(Hydroxymethyl)propylamide of 1-methyl-(+)-lysergic acid hydrogen maleate ; 1-Methyl-D-lysergic acid butanolamide dimaleate ; 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide maleate (1:1) (salt) ; Deseril ; Deseril-retard ; Desernil bismaleate ; EINECS 204-950-9 ; Ergoline-8-carboxamide, 9,10-didehydro-N-(1- (hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (Z)-2-butenedioate (1:1) (salt) ; Lysergamide, N-((1-hydroxymethyl)propyl)-1-methyl-, maleate ; Methysergide bimaleate ; Methysergide hydrogen maleate ; Methysergide maleate ; NSC 186061 ; Sansert ; UNII-2U7H1466GH ; Ergoline-8-beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, maleate(1:1) (salt) ; Ergoline-8-carboxamide, 9,10-didehydro-N-((1S)-1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (2Z)-2-butenedioate (1:1) (salt) ; Ergoline-8beta-carboxamide, 9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, maleate (1:2) (salt) (8CI)
CAS NO: 129-49-7
Molecular Formula of Methysergide dimaleate (CAS NO.129-49-7): C₂₅H₃₁N₃O₆
Molecular Weight: 469.5301
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 37.71 Å²
Flash Point: 337.5 °C
Enthalpy of Vaporization: 98.56 kJ/mol
Boiling Point: 634.4 °C at 760 mmHg
Vapour Pressure: 5.74E-17 mmHg at 25°C
Molecular Structure:

Methysergide dimaleate Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intravenous	185mg/kg (185mg/kg)	"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
mouse	LD50	oral	581mg/kg (581mg/kg)	"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rabbit	LD50	intravenous	28mg/kg (28mg/kg)	"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rat	LD50	intravenous	125mg/kg (125mg/kg)	"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.
rat	LD50	oral	200mg/kg (200mg/kg)	"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.

Methysergide dimaleate Safety Profile

Hazard Codes: T Toxic
Risk Statements of Methysergide dimaleate (CAS NO.129-49-7): 25
R25: Toxic if swallowed.
Safety Statements: 45
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: KE5410000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion and intravenous routes. Experimental reproductive effects. Human mutation effects reported. When heated to decomposition it emits toxic fumes of NO_x.

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