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66-83-1

Basic Information
CAS No.: 66-83-1
Name: 5-Methoxytryptamine hydrochloride
Article Data: 3
Cas Database
Molecular Structure:
Molecular Structure of 66-83-1 (5-Methoxytryptamine hydrochloride)
Formula: C11H15ClN2O
Molecular Weight: 226.706
Synonyms: 1H-Indole-3-ethanamine,5-methoxy-, monohydrochloride (9CI);Indole, 3-(2-aminoethyl)-5-methoxy-,monohydrochloride (8CI);5-Methoxytryptamine chloride;5-Methoxytryptaminemonohydrochloride;Mexamin;Mexamine;
EINECS: 200-637-6
Density: 1.171 g/cm3
Melting Point: 246 °C
Boiling Point: 380 °C at 760 mmHg
Flash Point: 183.6 °C
Solubility: N/A
Appearance: white to beige crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-20/21/22
Safety: 36-26
Transport Information: N/A
PSA: 51.04000
LogP: 3.18000
Synthetic route
52648-13-2

5-methoxytryptamine-2-carboxylic acid

66-83-1

5-methoxytryptamine hydrochloride

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

hydrogenchloride

73-31-4

5-methoxy-N-acetyl-tryptamine

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%
17952-87-3

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

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
775-16-6

N-benzyl-3-pyrrolidinone

66-83-1

5-methoxytryptamine hydrochloride

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%
50-00-0

formaldehyd

66-83-1

5-methoxytryptamine hydrochloride

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
28920-43-6

(fluorenylmethoxy)carbonyl chloride

66-83-1

5-methoxytryptamine hydrochloride

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%
66-83-1

5-methoxytryptamine hydrochloride

98-88-4

benzoyl chloride

76290-79-4

INS 48836

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

N-benzyl-3-pyrrolidinone

66-83-1

5-methoxytryptamine hydrochloride

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%
66-83-1

5-methoxytryptamine hydrochloride

108-24-7

acetic anhydride

73-31-4

5-methoxy-N-acetyl-tryptamine

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

5-methoxytryptamine hydrochloride

100-52-7

benzaldehyde

C18H18N2O*HCl

Conditions
ConditionsYield
for 0.05h; Pictet-Spengler cyclization; microwave irradiation;87%
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Chemistry

Molecular structure of 5-Methoxytryptamine hydrochloride (CAS NO.66-83-1) is:

Product Name: 5-Methoxytryptamine hydrochloride
CAS Registry Number: 66-83-1
IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)ethanamine hydrochloride 
Molecular Weight: 226.7026 [g/mol]
Molecular Formula: C11H15ClN2O
H-Bond Donor: 3
H-Bond Acceptor: 2
EINECS: 210-153-7
Sensitive: Hygroscopic
Melting Point: 246 °C
Surface Tension: 50.5 dyne/cm
Density: 1.171 g/cm3
Flash Point: 183.6 °C
Enthalpy of Vaporization: 62.81 kJ/mol
Boiling Point: 380 °C at 760 mmHg
Vapour Pressure: 5.61E-06 mmHg at 25°C
Product Categories: Tryptamines;Aminomethyl's;Pyrroles & Indoles;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Pyrroles & Indoles

Uses

 5-Methoxytryptamine hydrochloride (CAS NO.66-83-1) is used for a metabolite of melatonin.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 2500ug/kg (2.5mg/kg) CARDIAC: OTHER CHANGES
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
mouse LD50 intraperitoneal 227mg/kg (227mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1620, 1974.
mouse LD50 intravenous 103mg/kg (103mg/kg) BEHAVIORAL: TREMOR
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 23, Pg. T125, 1964.
mouse LD50 oral 580mg/kg (580mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 23, Pg. T125, 1964.
mouse LD50 subcutaneous 620mg/kg (620mg/kg)   Russian Pharmacology and Toxicology Vol. 35, Pg. 2, 1972.
rabbit LDLo intravenous 75mg/kg (75mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
rat LDLo intravenous 6mg/kg (6mg/kg)   Russian Pharmacology and Toxicology Vol. 33, Pg. 246, 1970.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-36/37/38-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36-26 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: NL4059000
F: 10
HazardClass: IRRITANT

Specification

 5-Methoxytryptamine hydrochloride (CAS NO.66-83-1) also can be called 3-(2-Aminoethyl)-5-methoxyindole hydrochloride ; Mexamine HCl ; Indole, 3-(2-aminoethyl)-5-methoxy-, hydrochloride ; and; 5-Methoxy-1H-indole-3-ethylamine monohydrochloride .It is a white to beige crystalline powder.