U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Molecular Formula C12H16N2
Molecular Weight 188.2688
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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 It was withdrawn from the market due to problems with agranulocytosis and other side effects.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.

CNS Activity

Originator

Approval Year

1961
146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Monase

Approved Use

Depression

Launch Date

1960
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8099943/
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
Other AEs: Palpitation, Nervousness...
Other AEs:
Palpitation (3 patients)
Nervousness (3 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
Other AEs: Palpitation, Nervousness...
Other AEs:
Palpitation (4 patients)
Nervousness (4 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
700 mg single, oral
Overdose
Dose: 700 mg
Route: oral
Route: single
Dose: 700 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3776356
unknown
n = 1
Health Status: unknown
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/3776356
Other AEs: Malignant hyperthermia...
Other AEs:
Malignant hyperthermia (grade 5, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3776356
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 5
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
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:
https://pubmed.ncbi.nlm.nih.gov/13750393
unhealthy, 61-93 years
n = 24
Health Status: unhealthy
Condition: depression
Age Group: 61-93 years
Sex: M+F
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/13750393
Malignant hyperthermia grade 5, 1 patient
700 mg single, oral
Overdose
Dose: 700 mg
Route: oral
Route: single
Dose: 700 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/3776356
unknown
n = 1
Health Status: unknown
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/3776356
Sourcing

Sourcing

Vendor/AggregatorIDURL
3B Scientific (Wuhan) Corp
3B3-053108
http://www.3bsc.com/index/pro_info.php?id=91573
AHH Chemical co.,ltd
MT-24552
http://www.ahhchemical.com/product/MT-24552.html
Ambinter
Amb1899372
http://www.ambinter.com/reference/1899372
Aurora Fine Chemicals LLC
A12.899.071
http://online.aurorafinechemicals.com/info?ID=A12.899.071
Aurora Fine Chemicals LLC
K01.620.385
http://online.aurorafinechemicals.com/info?ID=K01.620.385
ChemBridge
5119458
http://www.hit2lead.com/comp.asp?db=SC&id=5119458
ChemBridge
5132927
http://www.hit2lead.com/search.asp?db=SC&ids=5132927
Chemspace
CSSS00000129626
https://chem-space.com/CSSS00000129626
Clearsynth
CS-T-54609
https://www.clearsynth.com/en/CST54609.html
MuseChem
R064877
https://www.musechem.com/product/R064877.html
Smolecule
S527628
http://www.smolecule.com/products/s527628
THE BioTek
bt-267947
https://www.thebiotek.com/product/inhibitors/bt-267947
mcule
MCULE-8710039661
https://mcule.com/MCULE-8710039661/
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 (ETRYPTAMINE): AN ELECTROENCEPHALOGRAPHIC, BEHAVIORAL AND NEUROCHEMICAL ANALYSIS.
1963 Jul 2
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.
2006 Oct
Patents

Patents

US3296072A
3
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:17:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:17:30 GMT 2023
Record UNII
GR181O3R32
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 16:17:30 GMT 2023 , Edited by admin on Fri Dec 15 16:17:30 GMT 2023
WIKIPEDIA Designer-drugs-Monase
Created by admin on Fri Dec 15 16:17:30 GMT 2023 , Edited by admin on Fri Dec 15 16:17:30 GMT 2023
NCI_THESAURUS C667
Created by admin on Fri Dec 15 16:17:30 GMT 2023 , Edited by admin on Fri Dec 15 16:17:30 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1117
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
DRUG BANK
DB01546
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
SMS_ID
100000082116
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
EVMPD
SUB07347MIG
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
ChEMBL
CHEMBL1619758
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
INN
1276
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
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
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
MERCK INDEX
m727
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 Merck Index
MESH
C038034
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
CAS
2235-90-7
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
FDA UNII
GR181O3R32
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
PUBCHEM
8367
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
EPA CompTox
DTXSID1046764
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
INCB IDS CODE
PE 006
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
Related Record Type Details
Structure of ETRYPTAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of ETRYPTAMINE, (R)-
ENANTIOMER -> RACEMATE
Structure of ETRYPTAMINE, (S)-
ENANTIOMER -> RACEMATE
Structure of ETRYPTAMINE ACETATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of ETRYPTAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966