69937-13-9

Usage

Chemical Properties

Yellow Solid

Upstream product

• 858231-11-5 3-(2-chloro-ethyl)-5-nitro-indole 
• 124-40-3 dimethyl amine 
• 122110-09-2 5-nitroindole-3-N,N-dimethylglyoxamide 
• 6146-52-7 5-nitroindole 
• 6953-35-1 2-(5-nitro-1H-indol-3-yl)-2-oxoacetyl chloride 
• 166171-97-7 3-(2-bromoethyl)-5-nitro-1H-indole 

Downstream Products

• 99505-03-0 5-amino-3-(2-dimethylaminoethyl)-1H-indol 

Relevant academic research and scientific papers

5-arylindole derivatives

Compounds of formula (I), wherein R 1 is (a), (b), (c) or (d); n is 0, 1 or 2; A, B, C and D are each independently nitrogen or carbon; R 2, R 3, R 4 and R 5 are each independently hydrogen, C 1 to C 6 alkyl, aryl, C 1 to C 3 alkyl-aryl, halogen (e.g. fluorine, chlorine, bromine or iodine), cyano, nitro, --(CH 2) m NR 14 R 15, --(CH 2) m OR 9, --SR 9, --SO 2 NR 14 R 15, --(CH 2) m NR 14 SO 2 R 15 --(CH 2) m NR 14 CO 2 R 9, --(CH 2) m NR 14 COR 9, --(CH 2) m NR 14 CONHR 9, --CONR 14 R 15, or --CO 2 R 9 ; R 2 and R 3, R 3 and R 4, or R 4 and R 5 may be taken together to form a five- to seven-membered alkyl ring, a six-membered aryl ring, a five- to seven-membered heteroalkyl ring having 1 heteroatom of N, O, or S, or a five- to six-membered heteroaryl ring having H 1 or 2 heteroatoms of N, O, or S and the pharmaceutically acceptable salts thereof. These compounds are useful in treating migraine and other disorders. These compounds are useful psychotherapeutics and are potent serotonin (5-HT 1) agonists and benzodiazepine agonists and antagonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain and chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission. The compounds can also be used as centrally acting antihypertensives and vosodilators. STR1

INDOLE DERIVATIVES

Compounds of the formula STR1 wherein Z is STR2 R 1 is STR3 X is O, NH, or S; A, B, D, E, and F are each independently C, N, O, or S; wherein the remaining variables are defined in the specification, and the pharmaceutically acceptable salts thereof. Thes

ANTIMIGRAINE CYCLOBUTENEDIONE DERIVATIVES OF TRYPTAMINES

A series of serotonergic 5-cyclobutenedionylamino-substituted tryptamine derivatives of Formula I is disclosed for use in the alleviation of vascular headaches. STR1 The formula I substituents, as further defined in the specification, are: R 1 is hydrogen, halogen, and alkyl; R 2 and R 3 can be hydrogen or alkyl; R 4 is hydrogen, alkyl, acyl or alkylsulfonyl; m is 0 to 3 and n is 1 to 5; and X is amino, alkoxy, hydrogen, alkyl, aryl or alkylaryl.

A simple synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine]

A short (three step) synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N,N-dimethyltryptamine, 4] from commercially available starting materials is presented. Reaction of 5-nitroindole with oxalyl chloride followed by dimethylamine afforded N,N-dimethyl 5-nitroindole-3-glyoxamide (1), which was reduced by diborane to 5-nitro-3-(2-dimethylaminoethyl)indole (3). Catalytic reduction of (3) afforded the title compound in 19% overall yield from 5-nitroindole.