17274-65-6

Usage

Uses

Used in Research Applications:
5-Bromo-DMT is used as a research chemical for studying the effects of psychedelic substances on the brain. Its primary action is believed to be on serotonin receptors, similar to other psychedelics like LSD and psilocybin. This makes it a valuable tool for understanding the mechanisms of action of these compounds and their potential therapeutic applications.
Used in Pharmaceutical Development:
Although 5-Bromo-DMT itself has limited therapeutic benefits, its structural similarity to other tryptamines and its interaction with serotonin receptors make it a potential candidate for the development of new pharmaceuticals. Researchers may use it as a starting point for designing drugs with more specific and targeted effects, potentially leading to novel treatments for various mental health conditions.
Used in Forensic Toxicology:
As a controlled substance, 5-Bromo-DMT may be encountered in cases of drug abuse or overdose. Forensic toxicologists use analytical methods to detect and quantify the presence of 5-BROMO-N,N-DIMETHYLTRYPTAMINE in biological samples, such as blood or urine, to aid in investigations and legal proceedings.
Used in Drug Education and Awareness Programs:
Due to its hallucinogenic effects and potential for abuse, 5-Bromo-DMT is often included in drug education and awareness programs. These programs aim to inform the public about the risks associated with the use of psychedelic substances and promote responsible decision-making regarding drug use.
Used in Regulatory and Policy Development:
The classification of 5-Bromo-DMT as a controlled substance and its illegal status in many countries necessitate ongoing monitoring and evaluation of its prevalence, use patterns, and potential harms. This information is crucial for the development and implementation of effective drug policies and regulations aimed at reducing the negative consequences of drug abuse.

InChI:InChI=1/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

Synthetic route

4-(N,N-dimethylamino)butyraldehyde dimethyl acetal (19718-92-4) + 4-bromophenylhydrazine hydrochloride (622-88-8) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With sulfuric acid for 2h; Heating;	93%

2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide (717139-78-1) → 4-amino-2-(2-amino-5-bromo-phenyl)-4-dimethyl-butan-1-ol + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 25 - 27℃; for 12h; Stage #2: With 4 N NAOH In 1,2-dimethoxyethane at 80℃; for 0.5h; Stage #3: With 1,2-diaza-bicyclo[2.2.2]octane In 1,2-dimethoxyethane for 2h;	A n/a B 85%

2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide (717139-78-1) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -15 - 20℃; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane for 2h; Heating / reflux; Stage #3: With manganese(IV) oxide; sodium hydroxide; water more than 3 stages;	85%

methanol (67-56-1) + 5-bromotryptamine (3610-42-2) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With formaldehyd; nitrogen; sodium cyanoborohydride; acetic acid at 0 - 20℃; for 24h;	84%

2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide (199658-93-0) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; hexane; ethyl acetate	75%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Heating / reflux;

formaldehyd (50-00-0) + 5-bromotryptamine (3610-42-2) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With sodium acetate; sodium cyanoborohydride In methanol at 0 - 25℃; for 5h;	70.4%

5-bromo-1H-indole (10075-50-0) + 2-(N,N-dimethylamino)ethanol (108-01-0) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With C37H36Cl2NPRuS2; caesium carbonate at 135℃; for 24h; Inert atmosphere; Sealed tube;	40%

1-hydroxy-N,N-dimethyltryptamine (161202-91-1) → N,N-dimethyltryptamine (61-50-7) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) + 2-bromo-N,N-dimethyltryptamine

Conditions	Yield
With hydrogen bromide for 1h; Ambient temperature;	A 11% B 25% C 2%

2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide (199658-93-0) → N,N-dimethyltryptamine (61-50-7) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane for 3h; Heating;

5-bromotryptamine (3610-42-2) + methyl iodide (74-88-4) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Stage #1: 5-bromotryptamine With vinylsulfonylmethyl polystyrene In N,N-dimethyl-formamide Stage #2: methyl iodide In N,N-dimethyl-formamide Stage #3: With N-ethyl-N,N-diisopropylamine In dichloromethane Hoffman elimination; Further stages.;

indole (120-72-9) + (+-)-indolin-3-ol → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent 2: 70 percent / LiAlH4 3: 92 percent / triethylsilane, CF3COOH 4: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 5: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

N,N-dimethyltryptamine (61-50-7) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / triethylsilane, CF3COOH 2: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 3: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide (29095-44-1) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / LiAlH4 2: 92 percent / triethylsilane, CF3COOH 3: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 4: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

2-(dihydroindol-3-yl)-N,N-dimethylethylamine (38662-17-8, 79867-87-1) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 2: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

5-bromo-1H-indole (10075-50-0) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / 0 °C 2: H2O / 0.5 h 3: LiAlH4 / dioxane / 3 h / Heating View Scheme

2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride (63843-81-2) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 0.5 h 2: LiAlH4 / dioxane / 3 h / Heating View Scheme

4,4-diethoxy-N,N-dimethyl-1-butanamine (1116-77-4) + 4-bromophenylhydrazine hydrochloride (622-88-8) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
Stage #1: 4,4-diethoxy-N,N-dimethyl-1-butanamine; 4-bromophenylhydrazine hydrochloride With acetic acid In water for 4h; Fischer Indole Synthesis; Reflux; Stage #2: With sodium hydrogencarbonate In water pH=8 - 9;

formaldehyd (50-00-0) + 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (81868-12-4) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6)

Conditions	Yield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water at 20℃;

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → N,N-dimethyltryptamine (61-50-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 18h;	100%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-3-fluoro-2-oxoindole (1294480-65-1)

Conditions	Yield
With aluminum (III) chloride; Selectfluor In methanol; acetonitrile at 0 - 20℃; for 0.5h;	95%

1-(methylsulfonyl)-pyrrolidine (51599-68-9) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → almotriptan (154323-57-6)

Conditions	Yield
With nickel dichloride; lithium tert-butoxide; nixantphos In tetrahydrofuran at 0 - 80℃; for 13h; Reagent/catalyst; Inert atmosphere;	92%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) + methyl iodide (74-88-4) → 5-bromo-N,N,N-trimethyltryptamine

Conditions	Yield
In chloroform at 0 - 20℃;	88%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine (17380-42-6)

Conditions	Yield
With 1,1'-bis(diphenylphosphino)ferrocene; zink cyanide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In DMF (N,N-dimethyl-formamide) at 110℃; for 21h;	84%

dicyanozinc (557-21-1) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine (17380-42-6)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In DMF (N,N-dimethyl-formamide); chloroform at 110℃; for 21h; Product distribution / selectivity;	84%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc In hexanes; N,N-dimethyl-formamide at 20 - 60℃; for 0.75h;	37.6%

methanolic ammonia + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) + benzoyl chloride (98-88-4) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (208464-42-0)

Conditions	Yield
With dmap In dichloromethane; triethylamine	84%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) + benzoyl chloride (98-88-4) → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (208464-42-0)

Conditions	Yield
With triethylamine; dmap In dichloromethane at 20℃; for 20h;	84%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxaldehyde (152673-51-3)

Conditions	Yield
With tert.-butyl lithium In DMF (N,N-dimethyl-formamide); hexane at -75 - -30℃; for 1.33333h;	81.8%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → [2-(1-benzyl-5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine

Conditions	Yield
With sodium hydride; benzyl chloride In DMF (N,N-dimethyl-formamide)	76.6%

Benzyl propargyl ether (4039-82-1) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → {2-[5-(3-benzyloxy-prop-1-ynyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine (717139-86-1)

Conditions	Yield
With piperidine; tri-tert-butyl phosphine; copper(I) iodide; dichloro bis(acetonitrile) palladium(II) In hexane at 50℃; for 20h;	75%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 5-amino-3-(2-dimethylaminoethyl)-1H-indol (99505-03-0)

Conditions	Yield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 21h; Heating / reflux; Stage #3: With hydrogenchloride; sodium hydroxide; water more than 3 stages;	74.1%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → C12H15BrN2O (1310827-05-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 0.166667h; Inert atmosphere;	73%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → C17H24N2OS (208464-59-9)

Conditions	Yield
	34%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 3-[2-(N,N-Dimethylamino)ethyl]-5-(4-hydroxytetrahydropyran-4-yl)-1H-indole

Conditions	Yield
	30%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 5-(1-Aza-1-methyl-4-hydroxycyclohex-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions	Yield
With tert.-butyl lithium; potassium hydride In tetrahydrofuran	20%

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → 3-(2-dimethylamino-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one

Conditions	Yield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tert.-butyl lithium In diethyl ether; pentane at -78 - -30℃; for 1.25h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; pentane at -30 - -25℃; for 0.5h; Stage #3: In diethyl ether; chloroform; water; pentane at 20℃; for 1.5h;	15.3%

Upstream product

• 19718-92-4 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 199658-93-0 2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide 
• 161202-91-1 1-hydroxy-N,N-dimethyltryptamine 
• 3610-42-2 5-bromotryptamine 
• 74-88-4 methyl iodide 
• 120-72-9 indole 
• 61-50-7 N,N-dimethyltryptamine 
• 29095-44-1 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide 
• 717139-78-1 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide 
• 1116-77-4 4,4-diethoxy-N,N-dimethyl-1-butanamine 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 61-50-7 N,N-dimethyltryptamine 
• 99505-03-0 5-amino-3-(2-dimethylaminoethyl)-1H-indol 
• 17380-42-6 N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine 
• 717139-86-1 {2-[5-(3-benzyloxy-prop-1-ynyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine 
• 208464-42-0 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole 
• 185259-85-2 GR 46611 
• 154323-57-6 almotriptan 
• 208465-05-8 5-(1-aza-1-tert-butoxycarbonylcyclohex-3-en-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole 
• 208465-06-9 C₂₄H₂₆N₂O₂ 
• 208464-82-8 C₂₄H₂₆N₂O₂ 

Related news

Simple syntheses of lespedamine and 5-BROMO-N,N-DIMETHYLTRYPTAMINE (cas 17274-65-6) based on 1-hydroxyindole chemistry09/25/2019

Various types of 1-hydroxyindoles were prepared for the first time. Through methylation or acid catalyzed nucleophilic bromination ofN,N -dimethyl-1-hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.detailed

Relevant academic research and scientific papers

SIMPLE SYNTHESES OF LESPEDAMINE AND 5-BROMO-N,N-DIMETHYLTRYPTAMINE BASED ON 1-HYDROXYINDOLE CHEMISTRY

Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1-hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Indole derivatives and its application on the medicament

The invention provides indole derivatives or stereisomers, tautomers, nitrogen oxides, solvate, metabolic products, pharmaceutically acceptable salts or prodrugs thereof for treating the alzheimer disease. The invention further discloses a pharmaceutical composition containing the compounds and a method of using the compounds or the pharmaceutical composition thereof to treat the alzheimer disease.

Marine AChE inhibitors isolated from Geodia barretti: Natural compounds and their synthetic analogs

Barettin, 8,9-dihydrobarettin, bromoconicamin and a novel brominated marine indole were isolated from the boreal sponge Geodia barretti collected off the Norwegian coast. The compounds were evaluated as inhibitors of electric eel acetylcholinesterase. Barettin and 8,9-dihydrobarettin displayed significant inhibition of the enzyme, with inhibition constants (Ki) of 29 and 19 μM respectively towards acetylcholinesterase via a reversible noncompetitive mechanism. These activities are comparable to those of several other natural acetylcholinesterase inhibitors of marine origin. Bromoconicamin was less potent against acetylcholinesterase, and the novel compound was inactive. Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure-activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands for the acetylcholinesterase active site. The four natural compounds were also analysed for their butyrylcholinesterase inhibitory activity in addition and shown to display comparable activities. The study illustrates how both barettin and 8,9-dihydrobarettin display additional bioactivities which may help to explain their biological role in the producing organism. The findings also provide new insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.

Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus

A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC50 = 0.4 and 50 = 40.6 and >25 μM, respectively).

ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN

An enantioselective process for preparing zolmitriptan, (S)-4-{[3-[2-(dimethylamine)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone), by asymmetric hydrogenation of (Z)-2-(acetylamino)-3-{[3-N,N-(dimethylamine)ethyl)-1H-indol-5-yl]-2-propenoic acid methyl ester in the presence of hydrogen and an enantioselective chiral phosphine transition metal catalyst.

Method to Use Compositions Having Antidepressant Anxiolytic and Other Neurological Activity and Compositions of Matter

The sponges were collected from a variety of locations in the Florida Keys and separated based on morphology and color. The samples were identified as three species, two of which are well known: V. rigida (Esper, 1794) (order Verongida, family Aplysinidae) and S. aurea (Hyatt, 1875) (order Dictyoceratida, family Thorectidae), and a third S. cerebriformis (Duchassaing and Michelotti, 1864), is less common and separated based on subtle differences of morphology and coloration, from the other two species. Several compounds were isolated and were evaluated in established animal models predictive of neurological related drug function, namely, the rodent FST and the chick anxiety-depression model.

SYNTHESIS METHODS AND INTERMEDIATES FOR THE MANUFACTURE OF RIZATRIPTAN

The invention relates to a process for the manufacture of an 1,2,4-triazol-1-yl compound of the formula [A], or a salt thereof, wherein each of R3 and R4 is hydrogen or lower alkyl, said process comprising reacting a hydrazine compound of the formula [B] wherein R is hydrogen or acyl, R2 is hydrogen or a protecting group, are hydrogen or lower alkyl, and R6 is hydrogen or COOR7, or a salt thereof, with a 1,2,4-triazolyl forming reagent. In addition, novel intermediates for the synthesis of the anti-migraine agent Rizatriptan and methods for their synthesis are presented.

SYNTHESIS OF AMINES AND INTERMEDIATES FOR THE SYNTHESIS THEREOF

The invention relates in a first embodiment to a method for the manufacture of esters of the formula (I), or especially of amides of the formula (II), wherein the symbols have the meanings given in the specification, as well as other intermediates and compounds useful in the synthesis of tryptamines and other substances mentioned in the title. The synthesis methods and intermediates are useful in the synthesis of pharmaceuticals.

5-CYCLO INDOLE COMPOUNDS AS 5-HT1D RECEPTOR LIGANDS

Described herein are compounds selective for a 5-HT1D-like receptor, which have general formula (I), wherein A is selected from a six-membered, non-aromatic, optionally substituted carbocycle and a six-membered, non-aromatic, optionally substituted heterocycle having one or two heteroatoms selected from O, S, SO, SO2 and NR; R is selected from H and OH; n is 0 or 1 as permitted by chemical structure; R is selected from CRRCH2NRR or a group of formula (II), (III) or (IV); R is selected from H and benzoyl; R is selected from H, loweralkyl, benzyl, loweralkylcarbonyl, loweralkylaminocarbonyl; loweralkylaminothiocarbonyl, loweralkanoyl, loweralkylaminoimide and loweralkoxy-substituted loweralkylene; R and R are independently selected from H, loweralkoxy and hydroxy; R and R are independently selected from H and loweralkyl or R and R form an alkylene bridge which, together with the nitrogen atom to which they are attached, creates an optionally substituted 3- to 6-membered ring; ----- denotes a single or double bond; and R, R and R are independently selected from H and loweralkyl. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT1D-like receptor is implicated, such as migraine.