17274-65-6

Basic information

• Product Name: 5-BROMO-N,N-DIMETHYLTRYPTAMINE
• Synonyms: 5-BROMO-N,N-DIMETHYLTRYPTAMINE;5-Bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole;N,N-Dimethyl-5-bromo-1H-indole-3-ethanamine;2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethan-1-amine
• CAS NO: 17274-65-6
• Molecular Formula: C₁₂H₁₅BrN₂
• Molecular Weight: 267.16
• EINECS: 1592732-453-0
• Mol File: 17274-65-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 382.6 °C at 760 mmHg
• Flash Point: 185.2 °C
• Appearance: /
• Density: 1.397 g/cm³
• Vapor Pressure: 4.67E-06mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 5-BROMO-N,N-DIMETHYLTRYPTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-N,N-DIMETHYLTRYPTAMINE(17274-65-6)
• EPA Substance Registry System: 5-BROMO-N,N-DIMETHYLTRYPTAMINE(17274-65-6)

Safety Data

• Hazardous Substances Data: 17274-65-6(Hazardous Substances Data)

Usage

General Description

5-Bromo-N,N-dimethyltryptamine (5-Bromo-DMT) is a synthetic psychedelic drug that belongs to the tryptamine class. It is a derivative of the naturally occurring compound DMT, but with an added bromine atom. 5-Bromo-DMT is known for its hallucinogenic effects, including altered perception, visual and auditory hallucinations, and changes in mood and cognition. It is not commonly found or used recreationally and is illegal in many countries. Research on 5-Bromo-DMT is limited, but it is believed to act primarily on serotonin receptors in the brain, similar to other psychedelics like LSD and psilocybin. Due to its potential for abuse and lack of therapeutic benefits, it is classified as a controlled substance.

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

• 67-56-1 methanol 
• 3610-42-2 5-bromotryptamine 
• 10075-50-0 5-bromo-1H-indole 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 50-00-0 formaldehyd 
• 81868-12-4 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride 
• 1116-77-4 4,4-diethoxy-N,N-dimethyl-1-butanamine 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 717139-78-1 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide 
• 63843-81-2 2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 
• 38662-17-8 2-(dihydroindol-3-yl)-N,N-dimethylethylamine 
• 29095-44-1 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide 
• 61-50-7 N,N-dimethyltryptamine 
• 120-72-9 indole 

Downstream Products

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

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 articles and documents

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

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

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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.