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66-83-1 Usage

Chemical Properties

white to beige crystalline powder

Uses

Different sources of media describe the Uses of 66-83-1 differently. You can refer to the following data:
1. A closely related compound of the neurotransmitter Melatonin (M215000).
2. A metabolite of Melatonin

Biochem/physiol Actions

Nonselective serotonin receptor agonist that lacks affinity for the 5-HT3 receptor.

Check Digit Verification of cas no

The CAS Registry Mumber 66-83-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 6 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 66-83:
(4*6)+(3*6)+(2*8)+(1*3)=61
61 % 10 = 1
So 66-83-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3/p+1

66-83-1 Well-known Company Product Price

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  • Alfa Aesar

  • (L19070)  5-Methoxytryptamine hydrochloride, 98+%   

  • 66-83-1

  • 250mg

  • 221.0CNY

  • Detail
  • Alfa Aesar

  • (L19070)  5-Methoxytryptamine hydrochloride, 98+%   

  • 66-83-1

  • 1g

  • 614.0CNY

  • Detail
  • Alfa Aesar

  • (L19070)  5-Methoxytryptamine hydrochloride, 98+%   

  • 66-83-1

  • 5g

  • 2183.0CNY

  • Detail
  • Sigma

  • (M6628)  O-Methylserotoninhydrochloride  crystalline

  • 66-83-1

  • M6628-500MG

  • 1,743.30CNY

  • Detail
  • Sigma

  • (M6628)  O-Methylserotoninhydrochloride  crystalline

  • 66-83-1

  • M6628-1G

  • 3,125.07CNY

  • Detail

66-83-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Methoxy Tryptamine HCl

1.2 Other means of identification

Product number -
Other names 5-Methoxytryptamine hydrochloride

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:66-83-1 SDS

66-83-1Synthetic route

5-methoxytryptamine-2-carboxylic acid
52648-13-2

5-methoxytryptamine-2-carboxylic acid

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;72%
hydrogenchloride
7647-01-0

hydrogenchloride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

Conditions
ConditionsYield
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium dithionite; sodium hydroxide In 2-methyl-propan-1-ol at 100℃; for 2h; Inert atmosphere;
Stage #2: hydrogenchloride In 2-methyl-propan-1-ol; water Inert atmosphere;
25%
6-methoxy-2,3,4,9-tetrahydro-β-carbolin-1-one
17952-87-3

6-methoxy-2,3,4,9-tetrahydro-β-carbolin-1-one

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / KOH / ethanol / 6 h / Heating
2: 72 percent / 10percent aq. HCl / 2 h / Heating
View Scheme
N-benzyl-3-pyrrolidinone
775-16-6

N-benzyl-3-pyrrolidinone

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine]
853020-69-6, 853020-62-9, 853020-72-1

6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine]

Conditions
ConditionsYield
Stage #1: N-benzyl-3-pyrrolidinone; 5-methoxytryptamine hydrochloride With acetic acid at 100℃; for 1h;
Stage #2: With hydrogen; palladium 10% on activated carbon In ethanol for 72h;
Stage #3: With sodium carbonate In water Product distribution / selectivity;
99%
formaldehyd
50-00-0

formaldehyd

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

N,N-dimethyl-5-methoxytryptamine
1019-45-0

N,N-dimethyl-5-methoxytryptamine

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 0 - 25℃; for 2h;95%
With sodium cyanoborohydride
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

(9H-fluoren-9-yl)methyl 2-(5-methoxy-1H-indol-3-yl)ethylcarbamate
1394825-61-6

(9H-fluoren-9-yl)methyl 2-(5-methoxy-1H-indol-3-yl)ethylcarbamate

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate at 25℃; for 2h; Cooling;95%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

benzoyl chloride
98-88-4

benzoyl chloride

INS 48836
76290-79-4

INS 48836

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 20℃; for 2h;93%
N-benzyl-3-pyrrolidinone
775-16-6

N-benzyl-3-pyrrolidinone

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1'-benzyl-6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine]
853020-88-9, 853020-89-0, 853020-91-4

1'-benzyl-6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine]

Conditions
ConditionsYield
Stage #1: N-benzyl-3-pyrrolidinone; 5-methoxytryptamine hydrochloride With acetic acid at 100℃; for 1h;
Stage #2: With ammonia In methanol; chloroform; water
90.1%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

acetic anhydride
108-24-7

acetic anhydride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 3h;90%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

benzaldehyde
100-52-7

benzaldehyde

C18H18N2O*HCl

C18H18N2O*HCl

Conditions
ConditionsYield
for 0.05h; Pictet-Spengler cyclization; microwave irradiation;87%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

methyl chloroformate
79-22-1

methyl chloroformate

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate
67199-10-4

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;87%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C31H31N3O9S
308359-33-3

C31H31N3O9S

C42H43N5O9S
497871-10-0

C42H43N5O9S

Conditions
ConditionsYield
With sodium acetate In ethanol at 60℃; for 5h; Inert atmosphere;87%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

N-[2-(5-methoxyindol-3-yl)ethyl]-cyclobutylcarboxamide
147621-55-4

N-[2-(5-methoxyindol-3-yl)ethyl]-cyclobutylcarboxamide

Conditions
ConditionsYield
With potassium carbonate In chloroform; water for 0.5h; Ambient temperature;86%
Propyl isocyanate
110-78-1

Propyl isocyanate

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

S 20932

S 20932

Conditions
ConditionsYield
In diethyl ether for 0.5h; Ambient temperature;85%
1,10-phenanthroline-5,6-dione
27318-90-7

1,10-phenanthroline-5,6-dione

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

N,N'-(1,10-phenanthroline-5,6-diylidene)bis(2-(5-methoxy-1H-indol-3-yl)ethanamine)
1446204-34-7

N,N'-(1,10-phenanthroline-5,6-diylidene)bis(2-(5-methoxy-1H-indol-3-yl)ethanamine)

Conditions
ConditionsYield
In ethanol for 4h; Reflux;85%
1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1-indol-2-yl-6-methoxy-1,2,3,4-tetrahydro-β-carboline
136558-05-9

1-indol-2-yl-6-methoxy-1,2,3,4-tetrahydro-β-carboline

Conditions
ConditionsYield
In butan-1-ol for 2h; Heating;84%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

S 20760
139564-01-5

S 20760

Conditions
ConditionsYield
With potassium carbonate In chloroform; water for 0.5h; Ambient temperature;80%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

acetaldehyde
75-07-0

acetaldehyde

6-methoxy-1-methyl-1,2,3,4-tetrahydro-β-carboline
1210-56-6

6-methoxy-1-methyl-1,2,3,4-tetrahydro-β-carboline

Conditions
ConditionsYield
In water for 24h; Ambient temperature; pH=4.1 (phosphate buffer);79%
With hydrogenchloride In ethanol; water at 20℃; for 48h;19%
With acetate buffer for 48h; Ambient temperature; Yield given;
tert-butoxycarbonyl-5-methoxyindole-3-acetaldehyde
1616670-75-7

tert-butoxycarbonyl-5-methoxyindole-3-acetaldehyde

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1-(5-methoxy-1H-indol-3-yl)methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline

1-(5-methoxy-1H-indol-3-yl)methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline

Conditions
ConditionsYield
With acetic acid In water for 5h; Pictet-Spengler Synthesis; Reflux; Inert atmosphere;77%
6-ethoxy-2-methyl-quinoline
6628-28-0

6-ethoxy-2-methyl-quinoline

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C23H19N3O2

C23H19N3O2

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; Sealed tube; Green chemistry;75%
ethyl 4-(2-dimethylaminovinyl)-2-(piperidin-1-yl)pyrimidine-5-carboxylate

ethyl 4-(2-dimethylaminovinyl)-2-(piperidin-1-yl)pyrimidine-5-carboxylate

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

10-methoxy-2-(piperidin-1-yl)-8,13,13b,14-tetrahydroindolo[2,3-a]pyrimido[5,4-g]quinolizin-5(7H)-one
1030447-76-7

10-methoxy-2-(piperidin-1-yl)-8,13,13b,14-tetrahydroindolo[2,3-a]pyrimido[5,4-g]quinolizin-5(7H)-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Reflux;74%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

N-Butyryl-5-methoxytryptamine
66012-83-7

N-Butyryl-5-methoxytryptamine

Conditions
ConditionsYield
With sodium acetate In water; ethyl acetate for 3h;73%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

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

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

tert-butyl 6-methoxy-2,3,4,9-tetrahydro-1'H-spiro[β-carboline-1,3'-pyrrolidine]-1'-carboxylate
853020-73-2

tert-butyl 6-methoxy-2,3,4,9-tetrahydro-1'H-spiro[β-carboline-1,3'-pyrrolidine]-1'-carboxylate

Conditions
ConditionsYield
Stage #1: 5-methoxytryptamine hydrochloride; 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With acetic acid at 75℃; for 5h;
Stage #2: With ammonia In methanol; chloroform
73%
5-methoxyindole-3-carboxaldehyde
10601-19-1

5-methoxyindole-3-carboxaldehyde

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1-(5-methoxy-1H-indol-3-yl)-6-methoxy-1,2,3,4-tetrahydro-β-carboline
1616670-83-7

1-(5-methoxy-1H-indol-3-yl)-6-methoxy-1,2,3,4-tetrahydro-β-carboline

Conditions
ConditionsYield
Stage #1: 5-methoxyindole-3-carboxaldehyde; 5-methoxytryptamine hydrochloride In methanol for 24h; Pictet-Spengler Synthesis; Inert atmosphere; Reflux;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; for 19h; Pictet-Spengler Synthesis; Inert atmosphere;
73%
2-oxo-2H-pyran-6-carboxylic acid
672-67-3

2-oxo-2H-pyran-6-carboxylic acid

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

N-[2-(5-methoxy-indol-3-yI)-ethyl]-2-pyrone-6-carboxamide

N-[2-(5-methoxy-indol-3-yI)-ethyl]-2-pyrone-6-carboxamide

Conditions
ConditionsYield
Stage #1: 5-methoxytryptamine hydrochloride With pyridine In 1,2-dimethoxyethane at 20℃; for 0.5h;
Stage #2: 2H-pyran-2-one-6-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In 1,2-dimethoxyethane at 0 - 20℃; for 3.25h;
72%
2,6-dimethylquinoline
877-43-0

2,6-dimethylquinoline

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C22H17N3O

C22H17N3O

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; Sealed tube; Green chemistry;71%
furan-2-yl-oxo-acetic acid methyl ester
33245-13-5

furan-2-yl-oxo-acetic acid methyl ester

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1-furan-2-yl-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester
600121-86-6

1-furan-2-yl-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
In methanol at 60℃;70%
6-chloro-2-methylquinoline
92-46-6

6-chloro-2-methylquinoline

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C21H14ClN3O

C21H14ClN3O

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; Sealed tube; Green chemistry;69%
ethyl 4-(2-dimethylaminovinyl)-2-morpholinopyrimidine-5-carboxylate

ethyl 4-(2-dimethylaminovinyl)-2-morpholinopyrimidine-5-carboxylate

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

10-methoxy-2-(morpholin-4-yl)-8,13,13b,14-tetrahydroindolo[2,3-a]pyrimido[5,4-g]quinolizin-5(7H)-one
1030485-87-0

10-methoxy-2-(morpholin-4-yl)-8,13,13b,14-tetrahydroindolo[2,3-a]pyrimido[5,4-g]quinolizin-5(7H)-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 5h; Reflux;68%
5’-azido-8-carboxymethylthio-5'-deoxy-2’,3’-O-isopropylideneadenosine
1383468-08-3

5’-azido-8-carboxymethylthio-5'-deoxy-2’,3’-O-isopropylideneadenosine

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C26H30N10O5S

C26H30N10O5S

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;68%
6-Bromo-2-methyl-quinoline
877-42-9

6-Bromo-2-methyl-quinoline

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

C21H14BrN3O

C21H14BrN3O

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 130℃; Sealed tube; Green chemistry;68%
5-bromovaleric acid methyl ester
5454-83-1

5-bromovaleric acid methyl ester

5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

1-<2-(5-Methoxy-3-indolyl)-ethyl>-piperidon-2
62977-69-9

1-<2-(5-Methoxy-3-indolyl)-ethyl>-piperidon-2

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In ethanol for 16h; Reflux;66%

66-83-1Relevant articles and documents

The crystalline forms of nine hydrochloride salts of substituted tryptamines

Belanger, Zachary S.,Chadeayne, Andrew R.,Golen, James A.,Manke, David R.,Pham, Duyen N. K.

, p. 615 - 620 (2021/10/14)

The crystal structures of the hydro chloride salts of nine substituted tryptamines, namely, 1-methyl trypt am mon ium chloride, C11H15N2 +·Cl-, (1), 2-methyl-1-phenyl trypt am mon ium chloride, C17H19N2 +·Cl-, (2), 5-meth oxy trypt am mon ium chloride, C11H15N2O+·Cl-, (3), 5-bromo trypt am mon ium chloride, C10H12BrN2 +·Cl-, (4), 5-chloro trypt am mon ium chloride, C10H12ClN2 +·Cl-, (5), 5-fluoro trypt am mon ium chloride, C10H12FN2 +·Cl-, (6), 5-methyl trypt am mon ium chloride, C11H15N2 +·Cl-, (7), 6-fluoro trypt am mon ium chloride, C10H12FN2 +·Cl-, (8), and 7-methyl trypt am mon ium chloride, C11H15N2 +·Cl-, (9), are reported. The seven tryptamines with N - H indoles, (3)-(9), show very similar structures, with N - H?Cl hydro gen-bonding networks forming two-dimensional sheets in the crystals. These sheets are combinations of R 4 2(8) and R 4 2(18) rings, and C 2 1(4) and C 2 1(9) chains. Substitution at the indole N atom reduces the dimensionality of the hydro gen-bonding network, with com pounds (1) and (2) demonstrating one-dimensional chains that are a combination of different rings and parallel chains.

N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents

Guengoer, Timur,Malabre, Patrice,Teulon, Jean-Marie,Camborde, Francoise,Meignen, Joelle,et al.

, p. 4307 - 4316 (2007/10/02)

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.

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