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Details

Stereochemistry RACEMIC
Molecular Formula C12H16N2
Molecular Weight 188.2688
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETRYPTAMINE

SMILES

CCC(N)CC1=CNC2=CC=CC=C12

InChI

InChIKey=ZXUMUPVQYAFTLF-UHFFFAOYSA-N
InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3

HIDE SMILES / InChI
ETRYPTAMINE (MONASE®), similar to the hallucinogenic tryptamines, is an inhibitor of monoamine oxidase, introduced for use as an antidepressant. It was withdrawn from the market due to problems with agranulocytosis and other side effects. However, it's activity is still under scientific investigation.

Approval Year

T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.2 h
single, oral
ETRYPTAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
50 mg 1 times / day multiple, oral
Highest studied dose
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
Other AEs: Palpitation, Nervousness...
Other AEs:
Palpitation (3 patients)
Nervousness (3 patients)
Sources:
30 mg 1 times / day multiple, oral
Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
Other AEs: Palpitation, Nervousness...
Other AEs:
Palpitation (4 patients)
Nervousness (4 patients)
Sources:
700 mg single, oral
Overdose
Dose: 700 mg
Route: oral
Route: single
Dose: 700 mg
Sources:
unknown
n = 1
Health Status: unknown
Sex: M
Population Size: 1
Sources:
Other AEs: Malignant hyperthermia...
Other AEs:
Malignant hyperthermia (grade 5, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nervousness 3 patients
50 mg 1 times / day multiple, oral
Highest studied dose
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
Palpitation 3 patients
50 mg 1 times / day multiple, oral
Highest studied dose
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
Nervousness 4 patients
30 mg 1 times / day multiple, oral
Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
Palpitation 4 patients
30 mg 1 times / day multiple, oral
Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
Malignant hyperthermia grade 5, 1 patient
700 mg single, oral
Overdose
Dose: 700 mg
Route: oral
Route: single
Dose: 700 mg
Sources:
unknown
n = 1
Health Status: unknown
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Clinical experiences with etryptamine in office practice.
1961 Feb
The effect of Monase in depressive states: a multi-blind pilot study.
1961 May
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.
2006 Oct
Patents

Patents

Name Type Language
ETRYPTAMINE
INCB:GREEN LIST   INN   MI  
INN  
Official Name English
1H-INDOLE-3-ETHANAMINE, .ALPHA.-ETHYL-
Systematic Name English
ALPHA-ETHYLTRYPTAMINE
Systematic Name English
.ALPHA.-ETHYLTRYPTAMINE
Systematic Name English
ETRYPTAMINE [INCB GREEN LIST]
Common Name English
NSC-88061
Code English
MONASE
Common Name English
.ALPHA.ET
Common Name English
etryptamine [INN]
Common Name English
RO 3-1932
Code English
3-(2-AMINOBUTYL)INDOLE
Systematic Name English
AET-
Common Name English
ETRYPTAMINE [MI]
Common Name English
Classification Tree Code System Code
WIKIPEDIA TiHKAL
Created by admin on Fri Dec 15 16:17:30 GMT 2023 , Edited by admin on Fri Dec 15 16:17:30 GMT 2023
DEA NO. 7249
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WIKIPEDIA Designer-drugs-Monase
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NCI_THESAURUS C667
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Code System Code Type Description
DRUG CENTRAL
1117
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PRIMARY
DRUG BANK
DB01546
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SMS_ID
100000082116
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PRIMARY
EVMPD
SUB07347MIG
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ChEMBL
CHEMBL1619758
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INN
1276
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PRIMARY
WIKIPEDIA
alpha-Ethyltryptamine
Created by admin on Fri Dec 15 16:17:30 GMT 2023 , Edited by admin on Fri Dec 15 16:17:30 GMT 2023
PRIMARY α-Ethyltryptamine (αET, AET), also known as etryptamine (INN, BAN, USAN), is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s. αET is structurally and pharmacologically related to αMT, α-methyltryptamine, and it is believed[4] its central stimulant activity is probably not due to its activity as an MAOI, but appears to stem from its structural relationship to the indolic psychedelics. In contrast to αMT, αET is less stimulating and hallucinogenic, its effects resembling more those of entactogens like MDMA ("Ecstasy").
NCI_THESAURUS
C72772
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PRIMARY
MERCK INDEX
m727
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PRIMARY Merck Index
MESH
C038034
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PRIMARY
CAS
2235-90-7
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PRIMARY
FDA UNII
GR181O3R32
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PRIMARY
PUBCHEM
8367
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PRIMARY
EPA CompTox
DTXSID1046764
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PRIMARY
INCB IDS CODE
PE 006
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PRIMARY