ETRYPTAMINE HYDROCHLORIDE

First approved in 1961

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H16N2.ClH
Molecular Weight	224.73
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MKCOVEABRYHUEN-UHFFFAOYSA-N

InChI=1S/C12H16N2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://pubchem.ncbi.nlm.nih.gov/compound/8367 | https://www.ncbi.nlm.nih.gov/pubmed/14048556 | https://www.ncbi.nlm.nih.gov/pubmed/17112572

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 It was withdrawn from the market due to problems with agranulocytosis and other side effects.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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://patents.google.com/patent/US3296072 https://books.google.ru/books?id=l1DrqgobbcwC&pg=PA102&lpg=PA102&dq=Monase retrieved from Hallucinogens: A Forensic Drug Handbook: Richard R. Laing, Barry L. Beyerstein, Jay A. Siegel, p.102 https://www.ncbi.nlm.nih.gov/pubmed/13685431 https://www.ncbi.nlm.nih.gov/pubmed/13765760	Primary		Approved 8429	Monase Approved Use Depression Launch Date -2.83996815E11

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Clinical experiences with etryptamine in office practice.	1961 Feb	13765760
The effect of Monase in depressive states: a multi-blind pilot study.	1961 May	13685431
ALPHA-ETHYLTRYPTAMINE (ETRYPTAMINE): AN ELECTROENCEPHALOGRAPHIC, BEHAVIORAL AND NEUROCHEMICAL ANALYSIS.	1963 Jul 2	14048556
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.	2006 Oct	17112572

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:43 UTC 2023` Edited by `admin` on `Fri Dec 15 15:53:43 UTC 2023`
Record UNII	H52WH7M1B6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETRYPTAMINE HYDROCHLORIDE

Common Name

English

.ALPHA.-ETHYLTRYPTAMINE HYDROCHLORIDE

Systematic Name

English

1H-INDOLE-3-ETHANAMINE, .ALPHA.-ETHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

ETRYPTAMINE HYDROCHLORIDE [INCB GREEN LIST]

Common Name

English

INDOLE, 3-(2-AMINOBUTYL)-, MONOHYDROCHLORIDE

Systematic Name

English

1H-INDOLE-3-ETHANAMINE, .ALPHA.-ETHYL-, HYDROCHLORIDE

Systematic Name

English

ETRYPTAMINE HYDROCHLORIDE [MI]

Common Name

English

INDOLE, 3-(2-AMINOBUTYL)-, HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

INCB IDS CODE

PE 006