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139264-17-8 Usage

References

https://www.drugbank.ca/drugs/DB00315
Rothner, A. D., et al. "Zolmitriptan oral tablet in migraine treatment: high placebo responses in adolescents." Headache the Journal of Head & Face Pain 46.1(2006):101.
Hedlund, C, et al. "Zolmitriptan nasal spray in the acute treatment of cluster headache: a meta-analysis of two studies. " Neurology49.9(2009):1315–1323.

Uses

adrenergic agonist, nasal decongestant

Brand name

Zomig (AstraZeneca); Zomig (IPR).

Uses

A Serotonin 5HTID-receptor agonist

Description

Zolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. It is mainly used in the acute treatment of migraine attacks with or without aura and cluster headaches. Zolmitriptan takes effect through binding to human 5-HT1Band 5-HT1Dreceptors, leading to cranial blood vessel constriction and the release of sensory neuropeptides through nerve endings in the trigeminal system. 

Chemical Properties

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-/m1/s1

139264-17-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1727009)  Zolmitriptan  United States Pharmacopeia (USP) Reference Standard 139264-17-8 1727009-200MG 4,794.66CNY Detail
TCI America (Z0024)  Zolmitriptan  >98.0%(HPLC)(T) 139264-17-8 1g 1,260.00CNY Detail
TCI America (Z0024)  Zolmitriptan  >98.0%(HPLC)(T) 139264-17-8 200mg 390.00CNY Detail

139264-17-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name zolmitriptan

1.2 Other means of identification

Product number -
Other names (S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]-2-oxazolidinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:139264-17-8 SDS

139264-17-8Synthetic route

(S)-3-(2-dimethylaminoethyl)-5-[2-oxo-1,3-oxazolidin-4-ylmethyl]-1H-indol-2-carboxylic acid
659738-69-9

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

zolmitriptan
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
ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride
868622-23-5

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

zolmitriptan
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%
formaldehyd
50-00-0

formaldehyd

(S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine
139264-15-6

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

zolmitriptan
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%
ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate
191864-24-1

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

zolmitriptan
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
4,4-diethoxy-N,N-dimethyl-1-butanamine
1116-77-4

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

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

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

zolmitriptan
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
4,4-diethoxy-N,N-dimethyl-1-butanamine
1116-77-4

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

(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one
152305-23-2

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

zolmitriptan
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;
4,4-diethoxy-N,N-dimethyl-1-butanamine
1116-77-4

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

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one
187975-62-8

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

zolmitriptan
139264-17-8

zolmitriptan

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

Zolmitriptan hydrochloride

zolmitriptan
139264-17-8

zolmitriptan

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 10 - 25℃; for 1.5h; Product distribution / selectivity;
4-(N,N-dimethylamino)butyraldehyde dimethyl acetal
19718-92-4

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

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one
187975-62-8

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

zolmitriptan
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;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

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

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

zolmitriptan
139264-17-8

zolmitriptan

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at -15 - 20℃; pH=9 - 11;
(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one
152305-23-2

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

zolmitriptan
139264-17-8

zolmitriptan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite / water / -10 - 30 °C
2.1: hydrogenchloride; tin(ll) chloride / water / 4 h / -10 - 5 °C
2.2: pH 8 - 9
3.1: water / 25 - 30 °C / pH 9
3.2: 85 - 90 °C / pH 2
3.3: pH 8 - 9
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite / water / -5 - 10 °C
1.2: -15 - 10 °C
2.1: hydrogenchloride / isopropyl alcohol / 75 - 90 °C
3.1: hydrogenchloride / water / Reflux
View Scheme
sodium stearyl fumorate

sodium stearyl fumorate

zolmitriptan
139264-17-8

zolmitriptan

zolmitriptan
139264-17-8

zolmitriptan

Zolmitriptan N-oxide

Zolmitriptan N-oxide

Conditions
ConditionsYield
With sodium tungstate (VI) dihydrate; methanesulfonic acid; dihydrogen peroxide In methanol; water at 50 - 55℃;90%
zolmitriptan
139264-17-8

zolmitriptan

2-(S)-amino-3-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]propan-1-ol
139264-69-0

2-(S)-amino-3-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]propan-1-ol

Conditions
ConditionsYield
With sodium hydroxide In water83%
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

zolmitriptan
139264-17-8

zolmitriptan

C17H20F3N3O2

C17H20F3N3O2

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 60℃; Inert atmosphere; Sealed tube;45%
zolmitriptan
139264-17-8

zolmitriptan

(S)-2-{2-bromo-5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}dimethylethylamine

(S)-2-{2-bromo-5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}dimethylethylamine

Conditions
ConditionsYield
With trimethylsilyl bromide; dimethyl sulfoxide for 0.833333h; Ambient temperature;35%
zolmitriptan
139264-17-8

zolmitriptan

Zolmitriptan hydrochloride
139264-19-0

Zolmitriptan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 10℃; for 0.75h; Product distribution / selectivity; NaCl;
With hydrogenchloride In water Product distribution / selectivity; NaCl;
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

zolmitriptan
139264-17-8

zolmitriptan

4-(S)-[3-(2-chloroethyl)-1H-indol-5-ylmethyl]oxazolidin-2-one
1456510-16-9

4-(S)-[3-(2-chloroethyl)-1H-indol-5-ylmethyl]oxazolidin-2-one

Conditions
ConditionsYield
In toluene for 8h; Reflux;5 g
oxalic acid
144-62-7

oxalic acid

zolmitriptan
139264-17-8

zolmitriptan

(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium hydrogen oxalate

(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium hydrogen oxalate

Conditions
ConditionsYield
In methanol; water
(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

zolmitriptan
139264-17-8

zolmitriptan

[(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium (S,R)-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonate]

[(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium (S,R)-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonate]

Conditions
ConditionsYield
In methanol
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

zolmitriptan
139264-17-8

zolmitriptan

(S)-4-((1-(4-chlorobenzyl)-3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one

(S)-4-((1-(4-chlorobenzyl)-3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 0 - 23℃; Inert atmosphere;

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