Welcome to LookChem.com Sign In|Join Free

CAS

  • or

61-54-1

Post Buying Request

61-54-1 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

61-54-1 Usage

Description

Different sources of media describe the Description of 61-54-1 differently. You can refer to the following data:
1. Tryptamine is a monoamine alkaloid that can be synthesized by decarboxylation of the amino acid tryptophan. Notably, tryptamine can be found in fungi, plants, Amphibia, animals, and microbes. Tryptamine has an indole ring structure and a fused double ring that is composed of a benzene ring and a pyrrole ring, linked to an amino group by 2-carbon side chain. The indole ring is the vital nucleus of many complex natural products that have significance in drug discovery as well as some synthetic and non-synthetic drugs that are based on tryptamine skeleton. The chemical’s distinct structure is an approximation to the neurotransmitter serotonin as well-known drugs and hallucinogens. Tryptamine’s significance as psychedelic drugs, neuromodulator, and neurotransmitter is well understood due to its presence in mammalian brain in small amounts.
2. Tryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants. It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus. Tryptamine is also a product of tryptophan metabolism in mammals. Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.

Applications

Analogs of tryptamine that are typically produced by its synthetic modification play a significant role in individuals due to the introduction of functionalities that are biologically active in its nucleus that may cause changes in the mental and physical status of the human brain. Substitutions on the indole ring at nitrogen and C-2 of its side chain produce numerous neuroactive compounds ranging from anti-migraine drugs to toxic substances, such as rizatriptan, sumatriptan, and zolmitriptan. A small amount of tryptamine is required due to its fatalities and intoxication for several reasons.

Plants Containing Tryptamine

In plants, tryptamine in small amounts acts as a promising phase to the plant hormone indole-3-acetic acid in one biosynthetic pathway. N, N-dimethyltryptamine (DMT) is a tryptamine derivative that is an active constituent for the hallucinogenic effect of brew known as the “vine of the souls.” Indigenous Amazonian tribes have traditionally used the drink for therapeutic purposes for effective treatment of some physical maladies and abuse disorders. Magic mushrooms are the most common fungi that contain tryptamine derivatives.

Pharmacology

Serotonin (5-hydroxytryptamine, 5-HT), which is a natural derivative of tryptamine is a significant signaling hormone that helps in the modulation and regulation of numerous processes within the central nervous system, for instance, cognition, sleep, temperature regulation, memory, and behavior. The mammalian brain contains small traces of tryptamine, which generally act as a modulator or neurotransmitter by releasing serotonin agents. It is also an enhancer of serotonergic activity. Only one minute is required for tryptamine to produce psychotropic phenomena when used recreationally. It has been associated with fatalities and intoxications for multiple reasons including low toxic concentrations.

Chemical Properties

Tryptamine is a biogenic imine derived from the decarboxylation of tryptophan. It is a white to orange crystalline Powder, melting point 118°C (decomposition at 145-146°C). Soluble in ethanol and acetone, almost insoluble in ether, benzene, chloroform and water.

Uses

Tryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.

Definition

ChEBI: Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium.

Preparation

Tryptamine, a monoamine alkaloid containing an indole ring structure is derived by the decarboxylation of amino acid tryptophan.The synthesis of tryptamines is typically conducted following a classic route starting with a Mannich reaction of an indole heterocycle, followed by quaternization of the amine, nucleophilic substitution with highly toxic cyanide and final reduction.

General Description

Tryptamines which are usually found in plants, fungi, animals, etc. are categorized under the monoamine alkaloids class of compounds.

Biochem/physiol Actions

Vasoactive; may have a neuromodulator function; biogenic amine formed from the decarboxylation of tryptophan by L-aromatic amino acid decarboxylase.

Purification Methods

Crystallise tryptamine from *benzene, Et2O (m 114o) or pet ether (m 118o). It has UV: 222n 276, 282 and 291nm (EtOH) and max 226, 275, 281 and 290nm (HCl). [Beilstein 22 II 346, 22 III/IV 4319, 22/10 V 45.]

Check Digit Verification of cas no

The CAS Registry Mumber 61-54-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 61-54:
(4*6)+(3*1)+(2*5)+(1*4)=41
41 % 10 = 1
So 61-54-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

61-54-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11116)  Tryptamine, 98+%   

  • 61-54-1

  • 10g

  • 251.0CNY

  • Detail
  • Alfa Aesar

  • (A11116)  Tryptamine, 98+%   

  • 61-54-1

  • 50g

  • 1022.0CNY

  • Detail
  • Sigma-Aldrich

  • (76706)  Tryptamine  analytical standard

  • 61-54-1

  • 76706-100MG

  • 616.59CNY

  • Detail
  • Vetec

  • (V900719)  Tryptamine  Vetec reagent grade, 98%

  • 61-54-1

  • V900719-5G

  • 176.67CNY

  • Detail
  • Vetec

  • (V900719)  Tryptamine  Vetec reagent grade, 98%

  • 61-54-1

  • V900719-25G

  • 448.11CNY

  • Detail
  • Aldrich

  • (193747)  Tryptamine  98%

  • 61-54-1

  • 193747-10G

  • 250.38CNY

  • Detail
  • Aldrich

  • (193747)  Tryptamine  98%

  • 61-54-1

  • 193747-50G

  • 1,020.24CNY

  • Detail

61-54-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tryptamine

1.2 Other means of identification

Product number -
Other names Tryptamine

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:61-54-1 SDS

61-54-1Synthetic route

3-(2-nitroethyl)indole
31731-23-4

3-(2-nitroethyl)indole

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr; for 24h;98%
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 7h; Sonication; chemoselective reaction;94%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 15h;86.94%
L-Tryptophan
73-22-3

L-Tryptophan

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h;98%
cyclohexenone In various solvent(s) at 154℃; for 1.5h;92.3%
With L-amino acid decarboxylase from Micrococcus percitreus AJ 1065; NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate In water at 30℃; for 0.5h; Product distribution; study of the inhibition of the enzyme by various amino acids and amines, inhibition of L-dopa in different buffer solutions;
tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate
1042701-07-4

tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
Stage #1: tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate With trifluoroacetic acid In dichloromethane at 0 - 25℃; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In water pH=> 7; Inert atmosphere; Saturated solution;
98%
With trifluoroacetic acid In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;98%
N-tosyl tryptamine
86658-78-8

N-tosyl tryptamine

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With pyrrolidine; samarium diiodide; water In tetrahydrofuran at 20℃; Inert atmosphere;94%
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
38750-13-9

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With hydrogen; palladium In ethanol; ethyl acetate under 22502.3 Torr;94%
indole
120-72-9

indole

L-serin
56-45-1

L-serin

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
Stage #1: indole; L-serin With engineered tryptophan synthase In methanol; aq. phosphate buffer at 75℃; for 12h; pH=8.0; Enzymatic reaction;
Stage #2: With pyridoxal 5'-phosphate; Ruminococcus gnavus L-tryptophan decarboxylase In methanol; aq. phosphate buffer at 37℃; pH=8.0; Enzymatic reaction;
92%
3-[(E)-2-nitroeth-1-enyl]-1H-indole
3156-51-2, 51870-94-1

3-[(E)-2-nitroeth-1-enyl]-1H-indole

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Reflux;89%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere;83.5%
With lithium aluminium tetrahydride; diethyl ether
tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
103549-24-2

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
In various solvent(s) at 150℃; for 1h; microwave irradiation;88%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 1h; Microwave irradiation;88%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 1h; Microwave irradiation;88%
N-benzoyltryptamine
4753-09-7

N-benzoyltryptamine

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With sodium hydroxide In water; ethylene glycol82%
3-indolylacetamide
879-37-8

3-indolylacetamide

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;81%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
N-Acetyltryptamine
1016-47-3

N-Acetyltryptamine

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 80℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);81%
With recombinant Arabidopsis thaliana histone deacetylase 14 In aq. buffer at 30℃; pH=8; Reagent/catalyst; Enzymatic reaction;
4-(4,8-Dimethoxy-naphthalen-1-ylmethyl)-N-[2-(1H-indol-3-yl)-ethyl]-benzenesulfonamide
126402-58-2

4-(4,8-Dimethoxy-naphthalen-1-ylmethyl)-N-[2-(1H-indol-3-yl)-ethyl]-benzenesulfonamide

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With ammonia borane In ethanol Irradiation;78%
indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 12h; Inert atmosphere;75%
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;74%
With lithium aluminium tetrahydride; diethyl ether
3-(2-azidoethyl)-1H-indole
63778-37-0

3-(2-azidoethyl)-1H-indole

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
Stage #1: 3-(2-azidoethyl)-1H-indole With formic acid; tris(2,2'-bipyridyl)ruthenium dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In methanol; N,N-dimethyl-formamide at 25℃; for 24h; Irradiation;
Stage #2: With di-tert-butyl dicarbonate; triethylamine In methanol; N,N-dimethyl-formamide at 25℃; for 12h;
72%
3-((Z)-2-Nitro-vinyl)-1H-indole

3-((Z)-2-Nitro-vinyl)-1H-indole

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With hydrogenchloride; iron In methanol; water for 0.5h; Heating;71%
tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
In diphenylether for 10h; Heating;63%
With Catharanthus roseus tryptophan decarboxylase In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;
2-(2,3-dihydro-2-oxo-3-indolyl)ethylamine
60716-71-4

2-(2,3-dihydro-2-oxo-3-indolyl)ethylamine

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;62%
4-chloro-1-hydroxy-1-butanesulfonate sodium
54322-20-2

4-chloro-1-hydroxy-1-butanesulfonate sodium

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With disodium hydrogenphosphate In ethanol at 70℃; for 6h;61%
With disodium hydrogenphosphate In ethanol at 70℃; for 6h;
(3-Indolyl)acetaldehyd-dimethylhydrazon
74321-36-1

(3-Indolyl)acetaldehyd-dimethylhydrazon

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With hydrogen; rhenium; nickel In methanol under 760 Torr; for 12h; Ambient temperature;52%
indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

A

tryptamine
61-54-1

tryptamine

B

1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
168209-33-4

1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 96h;A 38%
B 31%
indole-3-acetonitrile
771-51-7

indole-3-acetonitrile

A

tryptamine
61-54-1

tryptamine

B

3-(2-aminoethyl)-2,3-dihydro-1H-indole
13078-91-6

3-(2-aminoethyl)-2,3-dihydro-1H-indole

Conditions
ConditionsYield
With ammonia; nickel at 100℃; under 66195.7 Torr; Hydrogenation;
3-(2-bromoethyl)-1H-indole
3389-21-7

3-(2-bromoethyl)-1H-indole

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With ammonia; water
4-aminobutyrylaldehyde diethylacetal
6346-09-4

4-aminobutyrylaldehyde diethylacetal

phenylhydrazine
100-63-0

phenylhydrazine

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With zinc(II) chloride
indole-3-glyoxylamide
5548-10-7

indole-3-glyoxylamide

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran Heating;
With lithium aluminium tetrahydride In 1,4-dioxane for 34h; Heating;0.90 g
With lithium aluminium tetrahydride In 1,4-dioxane for 50h; Heating;
N-Methylhomoisoleucyltryptamine

N-Methylhomoisoleucyltryptamine

A

tryptamine
61-54-1

tryptamine

(-)-N-Methylhomoisoleucine

(-)-N-Methylhomoisoleucine

Conditions
ConditionsYield
With hydrogenchloride for 24h; Heating;
(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
96014-22-1

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

A

tryptamine
61-54-1

tryptamine

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
In sodium hydroxide
2-[1-(phenylsulfonyl)-1H-indol-3-yl]ethanamines
808134-47-6

2-[1-(phenylsulfonyl)-1H-indol-3-yl]ethanamines

tryptamine
61-54-1

tryptamine

Conditions
ConditionsYield
With sodium hydroxide for 2h; Heating; Yield given;
(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
212707-60-3

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide

A

tryptamine
61-54-1

tryptamine

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
In sodium hydroxide
tryptamine
61-54-1

tryptamine

phenyl isocyanate
103-71-9

phenyl isocyanate

N-[2-(1H-indol-3-yl)ethyl]-N'-phenylurea
32585-51-6

N-[2-(1H-indol-3-yl)ethyl]-N'-phenylurea

Conditions
ConditionsYield
Stage #1: tryptamine; phenyl isocyanate In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
In dichloromethane at 60℃; for 5h; Inert atmosphere; Sealed reaction vessel;98%
tryptamine
61-54-1

tryptamine

benzyl chloroformate
501-53-1

benzyl chloroformate

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
38750-13-9

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1h;100%
With N-ethyl-N,N-diisopropylamine In chloroform at 0 - 20℃; for 1h;100%
With sodium hydroxide In tetrahydrofuran97%
tryptamine
61-54-1

tryptamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-<2-(indol-3-yl)ethyl>acetamide
52191-26-1

2-chloro-N-<2-(indol-3-yl)ethyl>acetamide

Conditions
ConditionsYield
With potassium carbonate In dichloromethane Ambient temperature;100%
In dichloromethane100%
With triethylamine In tetrahydrofuran at 20℃; for 6h; Cooling with ice; Inert atmosphere;96%
tryptamine
61-54-1

tryptamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-tosyl tryptamine
86658-78-8

N-tosyl tryptamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;100%
With triethylamine In dichloromethane at 0 - 20℃;99%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;99%
tryptamine
61-54-1

tryptamine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

N-(2-(1H-indol-3-yl)ethyl)-4-phenylbutanamide
102181-30-6

N-(2-(1H-indol-3-yl)ethyl)-4-phenylbutanamide

Conditions
ConditionsYield
With Trimethyl borate In acetonitrile at 80℃; for 15h;100%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 15h;70%
at 180℃;
tryptamine
61-54-1

tryptamine

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Nb-formyltryptamine
6502-82-5

Nb-formyltryptamine

Conditions
ConditionsYield
for 24h; Reflux;100%
for 6h; Reflux;100%
With triethylamine In methanol at 100℃; for 16h; Inert atmosphere;97%
tryptamine
61-54-1

tryptamine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl 2-(1H-indole-3-yl)ethylcarbamate
67909-99-3

ethyl 2-(1H-indole-3-yl)ethylcarbamate

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane Ambient temperature;100%
With triethylamine In dichloromethane at 0℃; Inert atmosphere;99.4%
With sodium hydroxide In chloroform for 3h;95%
tryptamine
61-54-1

tryptamine

benzaldehyde
100-52-7

benzaldehyde

N-benzylidene-2-(1H-indol-3-yl)ethylamine
16979-93-4

N-benzylidene-2-(1H-indol-3-yl)ethylamine

Conditions
ConditionsYield
In toluene at 20℃; for 12h;100%
In methanol at 25℃; for 16h;70%
With molecular sives 4A In dichloromethane Ambient temperature;
tryptamine
61-54-1

tryptamine

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

(E)-3-[2-(1H-Indol-3-yl)-ethylamino]-acrylic acid methyl ester
194150-88-4

(E)-3-[2-(1H-Indol-3-yl)-ethylamino]-acrylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 5h; Ambient temperature;100%
tryptamine
61-54-1

tryptamine

ethyl acrylate
140-88-5

ethyl acrylate

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester
14487-98-0

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester

Conditions
ConditionsYield
In ethanol for 1h; Reflux;100%
In ethanol at 0℃; for 24h;83%
In tetrahydrofuran at 20℃; for 12h;83%
In ethanol at 0 - 20℃;80%
In ethanol
tryptamine
61-54-1

tryptamine

methyl chloroformate
79-22-1

methyl chloroformate

methyl 2-(1-H-indol-3-yl)ethylcarbamate
58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 0℃;100%
With triethylamine100%
With sodium hydroxide In ethyl acetate at 25℃; for 0.5h;95%
tryptamine
61-54-1

tryptamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
103549-24-2

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane for 1h;100%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.05h;100%
With amberlyst-15 In ethanol at 20℃; for 2h; chemoselective reaction;100%
tryptamine
61-54-1

tryptamine

3,6-diiodopyridazine
20698-04-8

3,6-diiodopyridazine

[2-(1H-indol-3-yl)-ethyl]-(6-iodo-pyridazin-3-yl)-amine
500733-95-9

[2-(1H-indol-3-yl)-ethyl]-(6-iodo-pyridazin-3-yl)-amine

Conditions
ConditionsYield
In iso-butanol for 96h; Heating;100%
tryptamine
61-54-1

tryptamine

3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine
2946-89-6

3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine

N-nitro-N'-[2-(1H-indol-3-yl)ethy]guanidine

N-nitro-N'-[2-(1H-indol-3-yl)ethy]guanidine

Conditions
ConditionsYield
In methanol at 20℃;100%
tryptamine
61-54-1

tryptamine

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

N-(2-(1H-indol-3-yl)ethyl)-2-nitrobenzenesulfonamide
311781-49-4

N-(2-(1H-indol-3-yl)ethyl)-2-nitrobenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;97%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere;97%
tryptamine
61-54-1

tryptamine

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

N-(2-(1H-indol-3-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide
372109-22-3

N-(2-(1H-indol-3-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 22℃; for 16h;
tryptamine
61-54-1

tryptamine

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
101385-93-7

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

spiro

spiro

Conditions
ConditionsYield
Stage #1: tryptamine; 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With acetic acid at 100℃; for 4.5h;
Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃;
100%
tryptamine
61-54-1

tryptamine

3,4,5-trifluoronitrobenzene
66684-58-0

3,4,5-trifluoronitrobenzene

C16H13F2N3O2
1132682-52-0

C16H13F2N3O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 120℃; for 18h;100%
tryptamine
61-54-1

tryptamine

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indol-1-yl)benzonitrile
1171311-06-0

3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indol-1-yl)benzonitrile

Conditions
ConditionsYield
With trifluoroacetic acid In 1,1-dichloroethane Reflux;100%
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; Pictet-Spengler Synthesis;18%
tryptamine
61-54-1

tryptamine

2,3-dichlorobenzylaldehyde
6334-18-5

2,3-dichlorobenzylaldehyde

C17H14Cl2N2
331852-79-0

C17H14Cl2N2

Conditions
ConditionsYield
With trifluoroacetic acid In 1,1-dichloroethane Reflux;100%
tryptamine
61-54-1

tryptamine

Boc-Trp-OH
13139-14-5

Boc-Trp-OH

(S)-Nα-tert-butoxycarbonyl-N-[2-(3-indolyl)ethyl]tryptophanamide
1244546-21-1

(S)-Nα-tert-butoxycarbonyl-N-[2-(3-indolyl)ethyl]tryptophanamide

Conditions
ConditionsYield
Stage #1: Boc-Trp-OH With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere;
Stage #2: tryptamine In dichloromethane at 20℃; Inert atmosphere;
100%
tryptamine
61-54-1

tryptamine

C11H22O2Si

C11H22O2Si

C21H34N2OSi
1448446-83-0

C21H34N2OSi

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In dichloromethane at 0℃; for 12h;100%
tryptamine
61-54-1

tryptamine

2-Methylbutyraldehyde
96-17-3, 57456-98-1

2-Methylbutyraldehyde

N-(2-(1H-indol-3-yl)ethyl)-2-methylbutan-1-amine
1038257-36-1

N-(2-(1H-indol-3-yl)ethyl)-2-methylbutan-1-amine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 2-methyltetrahydrofuran at 18℃; for 2h; Solvent; Green chemistry;100%
tryptamine
61-54-1

tryptamine

C73H8F3NO4

C73H8F3NO4

C79H15F3N2O

C79H15F3N2O

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;100%
tryptamine
61-54-1

tryptamine

pyrrol-2-yl trichloromethyl ketone
35302-72-8

pyrrol-2-yl trichloromethyl ketone

N-(2-(1H-indol-3-yl)ethyl)-1H-pyrrole-2-carboxamide
15776-55-3

N-(2-(1H-indol-3-yl)ethyl)-1H-pyrrole-2-carboxamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere;100%
tryptamine
61-54-1

tryptamine

ethylenesulfonyl fluoride
677-25-8

ethylenesulfonyl fluoride

2,2′-((2-(1H-indol-3-yl)ethyl)azanediyl)diethanesulfonyl fluoride

2,2′-((2-(1H-indol-3-yl)ethyl)azanediyl)diethanesulfonyl fluoride

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In dichloromethane at 20℃; for 6h;95%
tryptamine
61-54-1

tryptamine

2,4,6-triphenylpyrylium tetrafluoroborate
448-61-3

2,4,6-triphenylpyrylium tetrafluoroborate

1-(2-(1H-Indol-3-yl)ethyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

1-(2-(1H-Indol-3-yl)ethyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

Conditions
ConditionsYield
In ethanol at 85℃;100%
In ethanol at 85 - 90℃; for 4h; Schlenk technique;91%
With acetic acid In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;59%
In ethanol Reflux;
In ethanol at 80 - 85℃; for 4h; Inert atmosphere;
tryptamine
61-54-1

tryptamine

flufenamic acid
530-78-9

flufenamic acid

C14H10F3NO2*C10H12N2

C14H10F3NO2*C10H12N2

Conditions
ConditionsYield
In methanol at 20℃;100%
tryptamine
61-54-1

tryptamine

C17H15F3N2O3

C17H15F3N2O3

C17H15F3N2O3*C10H12N2

C17H15F3N2O3*C10H12N2

Conditions
ConditionsYield
In methanol at 20℃;100%
tryptamine
61-54-1

tryptamine

benzoyl chloride
98-88-4

benzoyl chloride

N-benzoyltryptamine
4753-09-7

N-benzoyltryptamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;99%
With sodium hydroxide In acetone at -30℃;95%
In dichloromethane82%

61-54-1Relevant articles and documents

-

Brutcher,Vanderwerff

, p. 146 (1958)

-

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta

, (2021/08/17)

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Concerning the preparation of 6-bromotryptamine

Scott Wiens,Johnson, Jerry L.,Gribble, Gordon W.

, (2021/03/15)

Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 61-54-1