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Details

Stereochemistry ACHIRAL
Molecular Formula C13H18N2O
Molecular Weight 218.2948
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXY-N-METHYL-N-ETHYLTRYPTAMINE

SMILES

CCN(C)CCC1=CNC2=C1C(O)=CC=C2

InChI

InChIKey=ORWQBKPSGDRPPA-UHFFFAOYSA-N
InChI=1S/C13H18N2O/c1-3-15(2)8-7-10-9-14-11-5-4-6-12(16)13(10)11/h4-6,9,14,16H,3,7-8H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C13H18N2O
Molecular Weight 218.2948
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

4-Hydroxy-N-methyl-N-ethyltryptamine (4-HO-MET) is a new psychoactive substance (NPS) of the chemical class of tryptamines. It shows structural similarities to the endogenous neurotransmitter serotonin, and is a serotonergic hallucinogen, affecting emotional, motoric, and cognitive functions. It is a structural and functional analog of psilocin as well as the 4-hydroxy analog of MET. 4-HO-MET was first synthesized by Alexander Shulgin. The effects of 4-HO-MET are quite comparable to the effects of psyloc(yb)in, which should be no surprise considering the structural similarities between these compounds. As with other hallucinogens, alterations of color, time, music have been reported (synesthesia). Extensive time dilatation has been reported. The overall effects have been reported to be very comparable to those of psiloc(yb)in. Comparable to psilocin, the mental health risks include fear, anxiety and paranoia. Treatment of intoxication is symptomatic: calming the patient, transferring to a non-discomforting room. In severe cases an anxiolytic (diazepam, alprazolam) can be used. Antidote: The hallucinogenic effects can be totally reversed by administration of a 5-HT2A antagonist, such as Zyprexa.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
37.0 nM [EC50]
Target ID: P28335
Gene ID: 3358.0
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
141.0 nM [Ki]
Target ID: P08908
Gene ID: 3350.0
Gene Symbol: HTR1A
Target Organism: Homo sapiens (Human)
228.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Heaven and hell--a phenomenological study of recreational use of 4-HO-MET in Sweden.
2011 Jul-Sep
A Fatality Related to Two Novel Hallucinogenic Compounds: 4-Methoxyphencyclidine and 4-Hydroxy-N-methyl-N-ethyltryptamine.
2015 Nov-Dec
Study of the in vitro and in vivo metabolism of 4-HO-MET.
2018 Sep

Sample Use Guides

Dosages of 10-20 mg orally have been reported by Alexander Shulgin. The reported duration of effects lasted between 4 and 6 hours
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:32:24 UTC 2023
Edited
by admin
on Sat Dec 16 10:32:24 UTC 2023
Record UNII
6RN01B78NY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXY-N-METHYL-N-ETHYLTRYPTAMINE
Systematic Name English
4-HO-MET
Common Name English
COLOUR
Common Name English
METHYLCYBIN
Common Name English
METOCIN
Common Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-4-HO-MET
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
WIKIPEDIA TiHKAL
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID70228491
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
CAS
77872-41-4
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
SMS_ID
100000170016
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
EVMPD
SUB183762
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
PUBCHEM
21786582
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
WIKIPEDIA
4-HO-MET
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
FDA UNII
6RN01B78NY
Created by admin on Sat Dec 16 10:32:24 UTC 2023 , Edited by admin on Sat Dec 16 10:32:24 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
OFF-TARGET->INHIBITOR
TARGET -> AGONIST
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY