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139264-17-8

Basic Information
CAS No.: 139264-17-8
Name: Zolmitriptan
Article Data: 17
Molecular Structure:
Molecular Structure of 139264-17-8 (Zolmitriptan)
Formula: C16H21N3O2
Molecular Weight: 287.362
Synonyms: Zomig Nasal Spray;311C90;Zomig (TN);Zolmitriptan (JAN/USAN);2-Oxazolidinone,4-[[3-[2-(dimethylamino)- ethyl]-1H-indol-5-yl]methyl]-,(4S)-;(4S)-4-[[3-(2-dimethylaminoethyl)-1H-indol-5-yl]methyl]oxazolidin-2-one;Zomig;Zolmitriptan [USAN];4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone;2-Oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-, (S)-;Zomig ZMT;Zolmitriptan [GMP];Zolmitrptan;
EINECS: 629-919-0
Density: 1.217 g/cm3
Melting Point: 136-141 °C
Boiling Point: 563.3 °C at 760 mmHg
Flash Point: 294.5 °C
Appearance: White or kind of white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 57.36000
LogP: 2.25170
Synthetic route
659738-69-9

(S)-3-(2-dimethylaminoethyl)-5-[2-oxo-1,3-oxazolidin-4-ylmethyl]-1H-indol-2-carboxylic acid

139264-17-8

zolmitriptan

Conditions
ConditionsYield
copper(II) oxide In quinoline at 200℃; for 0.333333h;90%
With hydrogenchloride In water at 15 - 18℃; Reflux; Industrial scale;1.75 kg
868622-23-5

ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride

139264-17-8

zolmitriptan

Conditions
ConditionsYield
Stage #1: ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride With water; sodium carbonate for 2 - 2.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 15 - 18℃; for 3h; Heating / reflux;
Stage #3: With sodium hydroxide In water at 15 - 20℃; pH=9.75 - 10; Product distribution / selectivity;
77%
50-00-0

formaldehyd

139264-15-6

(S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine

139264-17-8

zolmitriptan

Conditions
ConditionsYield
Stage #1: formaldehyd; (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine With sodium cyanoborohydride; acetic acid In methanol; water at 5 - 20℃; for 2h;
Stage #2: With potassium carbonate In methanol; water pH=10 - 11; Product distribution / selectivity;
74%
With sodium cyanoborohydride; acetic acid In methanol Ambient temperature;31%
191864-24-1

ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate

139264-17-8

zolmitriptan

Conditions
ConditionsYield
Stage #1: ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate With water; sodium carbonate for 2 - 2.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water for 4h; Heating / reflux;
Stage #3: With sodium hydroxide In water at 15 - 20℃; pH=9.75 - 10; Product distribution / selectivity;
45%
Multi-step reaction with 2 steps
1: sodium carbonate / water / Reflux; Industrial scale
2: hydrogenchloride / water / 15 - 18 °C / Reflux; Industrial scale
View Scheme
1116-77-4

4,4-diethoxy-N,N-dimethyl-1-butanamine

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride

139264-17-8

zolmitriptan

Conditions
ConditionsYield
In water at 90℃; for 3h; Fischer Indole Synthesis; Heating / reflux;
With hydrogenchloride In water Reflux;62 g
With hydrogenchloride In water Reflux; Large scale;8.2 kg
1116-77-4

4,4-diethoxy-N,N-dimethyl-1-butanamine

152305-23-2

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one

139264-17-8

zolmitriptan

Conditions
ConditionsYield
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With sodium metabisulfite; sodium hydroxide In water at 2 - 60℃; for 1.25h; Heating / reflux;
Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine With hydrogenchloride; sodium hydroxide more than 3 stages;
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0℃; for 1.5h;
Stage #2: With sodium sulfite In water at 0 - 60℃;
Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: With sodium sulfite In water at 10℃; for 0.25h;
Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine With hydrogenchloride Product distribution / selectivity; more than 3 stages;
1116-77-4

4,4-diethoxy-N,N-dimethyl-1-butanamine

187975-62-8

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one

139264-17-8

zolmitriptan

Conditions
ConditionsYield
at 90 - 98℃; for 2.5h; Product distribution / selectivity; Heating / reflux;
139264-19-0

Zolmitriptan hydrochloride

139264-17-8

zolmitriptan

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 10 - 25℃; for 1.5h; Product distribution / selectivity;
19718-92-4

4-(N,N-dimethylamino)butyraldehyde dimethyl acetal

187975-62-8

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one

139264-17-8

zolmitriptan

Conditions
ConditionsYield
Stage #1: 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal; (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride In water at 25 - 90℃; for 5 - 6h; pH=2 - 9;
Stage #2: With sodium carbonate In water pH=~ 8 - 9;
Stage #1: 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal; (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one In water at 25 - 30℃; pH=9;
Stage #2: With hydrogenchloride In water at 85 - 90℃; pH=2;
Stage #3: With sodium carbonate In water pH=8 - 9;
32315-10-9

bis(trichloromethyl) carbonate

(S)-2-amino-3-{[3-N,N-dimethylamino-ethyl]-1H-indol-5-yl}-1-propanol dihydrochloride

139264-17-8

zolmitriptan

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at -15 - 20℃; pH=9 - 11;
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139264-69-0
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Chemistry

Molecular Structure of Zolmitriptan (CAS NO.139264-17-8):

IUPAC Name: (4R)-4-[[3-(2-dimethylaminoethyl)-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one
Molecular formula: C16H21N3O2
Molecular Weight: 287.36
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 37.71Å2
Index of Refraction: 1.619
Molar Refractivity: 82.89 cm3
Molar Volume: 236.1 cm3
Surface Tension: 53 dyne/cm
Density: 1.217 g/cm3
Flash Point: 294.5 °C
Enthalpy of Vaporization: 84.66 kJ/mol
Boiling Point: 563.3 °C at 760 mmHg
Vapour Pressure: 1.03E-12 mmHg at 25°C
Melting point: 136-141°C
Appearance: White Crystalline Powder
InChI
InChI=1/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
Smiles
c12c([nH]cc1CCN(C)C)ccc(c2)C[C@@H]1NC(=O)OC1
Product Categories: Antimigraine; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Zolmitriptan

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
women TDLo oral 6mg/kg/43W-I (6mg/kg) BEHAVIORAL: HEADACHE Lancet. Vol. 353, Pg. 378, 1999.
 

Safety Profile

Hazard Codes:  Xi
The Risk Statements information of  Zolmitriptan:
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information of  Zolmitriptan:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

Specification

  Zolmitriptan , with CAS number of 139264-17-8, can be called (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone ; (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone ; 2-Oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-, (S)- ; 4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone . The usage of Zolmitriptan is as an serotonin 5HTID-receptor agonist.

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