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121679-20-7

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121679-20-7 Usage

Uses

Naratriptan related compound B. Naratriptan impurity B.

Biological Activity

pki: 8.9 of naratriptan for human 5-ht1b3,4-dihydro naratriptan is a selective serotonin 5-ht1b agonist.5-ht1b receptors are widely distributed throughout the cns with the highest concentrations found in the basal ganglia, frontal cortex, striatum, and the hippocampus. the function of the 5-ht1b receptor differs depending upon its location.

in vitro

3,4-dihydro naratriptan is an impurity formed during the preparation of naratriptan. naratriptan had high affinity for human recombinant 5ht1b and 5ht1d receptors and could cause contractions of dog isolated basilar and middle cerebral artery. naratriptan also caused small contractions of human isolated coronary arteries [1].

in vivo

in anaesthetized dogs, naratriptan caused selective vasoconstriction of the carotid arterial bed and, in anaesthetized rats, naratriptan selectively inhibited neurogenic plasma protein extravasation in the dura. in various antinociceptive tests, naratriptan had no effect even at high doses. in conscious rats and dogs, naratriptan had high oral bioavailability [1].

references

[1] connor he, feniuk w, beattie dt, north pc, oxford aw, saynor da, humphrey pp. naratriptan: biological profile in animal models relevant to migraine. cephalalgia. 1997 may;17(3):145-52.[2] dulli da. naratriptan: an alternative for migraine. ann pharmacother. 1999 jun;33(6):704-11.

Check Digit Verification of cas no

The CAS Registry Mumber 121679-20-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,6,7 and 9 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 121679-20:
(8*1)+(7*2)+(6*1)+(5*6)+(4*7)+(3*9)+(2*2)+(1*0)=117
117 % 10 = 7
So 121679-20-7 is a valid CAS Registry Number.
InChI:InChI=1/C17H23N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-5,11-12,18-19H,6-10H2,1-2H3

121679-20-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N-methyl-2-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide

1.2 Other means of identification

Product number -
Other names 3,4-Didehydronaratriptan

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:121679-20-7 SDS

121679-20-7Relevant articles and documents

The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan

Zhang, Mingjun,Chen, Miaomiao,Ding, Xin,Kang, Jin,Gao, Yongyue,He, Xingxing,Wang, Ziwen,Lu, Aidang,Wang, Qingmin

, p. 9140 - 9143 (2021/09/14)

The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.

A PROCESS FOR THE SYNTHESIS OF NARATRIPTAN

-

, (2011/04/13)

The present invention relates to a process for preparing naratriptan or a salt thereof, the process comprising: (a) reacting a compound of formula (3) with a compound of the formula HCCR wherein Z is a protecting group, Y is a leaving group and R is a trialkyl silyl group, a trialkylstannyl group or a zinc (II) halide, to obtain the compound of formula (4); (b) converting the compound of formula (4) to a compound of formula (5) wherein Z'' is hydrogen or a benzyl group; (c) converting the compound of formula (5) to naratriptan; and (d) optionally converting naratriptan to a salt thereof. The present invention also provides novel compounds (3) and (4) and processes for their preparation.

PROCESS FOR PREPARATION OF NARATRIPTAN HYDROCHLORIDE

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Page/Page column 27, (2009/10/22)

The present invention relates to an improved process for the preparation of N-methyl-3- (1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride of formula (I) having less than 0.15 % area by HPLC of 3-(1-methyl-4-piperidinyl)-1H-indole-5- ethanesulfonamide (1A) and intermediates thereof.

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