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Details

Stereochemistry RACEMIC
Molecular Formula C15H21NO2
Molecular Weight 247.3327
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Methoxetamine

SMILES

CCNC1(CCCCC1=O)C2=CC(OC)=CC=C2

InChI

InChIKey=LPKTWLVEGBNOOX-UHFFFAOYSA-N
InChI=1S/C15H21NO2/c1-3-16-15(10-5-4-9-14(15)17)12-7-6-8-13(11-12)18-2/h6-8,11,16H,3-5,9-10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C15H21NO2
Molecular Weight 247.3327
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Methoxetamine (abbreviated as MXE) is a novel psychoactive substance that is emerging on the Internet and induces dissociative effects and acute toxicity. MXE acts behaviourally as a typical dissociative anesthetic with stimulant and anxiogenic effects at lower doses, sedative/anesthetic effects at higher doses, and as a disruptor of sensorimotor gating. Its pharmacological effects have not yet been adequately investigated, but recently published articles shown, that MXE differentially affected motor activity, behavior and emotional states in rats, depending on the dose tested. Methoxetamine acts mainly as N-methyl-D-aspartate (NMDA) receptor antagonist and a serotonin reuptake inhibitor.

CNS Activity

Curator's Comment: Known to be CNS active in rats. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41594
Gene ID: 2915.0
Gene Symbol: GRM5
Target Organism: Homo sapiens (Human)
259.0 nM [Ki]
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
481.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Neuropharmacological characterization of the new psychoactive substance methoxetamine.
2017 Sep 1

Sample Use Guides

in rats: Methoxetamine (MXE) (0.5-5 mg·kg-1) affected motor activity in a dose- and time-dependent manner, inducing hypermotility and hypomotility at low and high doses respectively. At low and intermediate doses (0.5 and 1 mg·kg-1), MXE induced anxious and/or obsessive-compulsive traits (marble burying test), did not significantly increase sociability (social interaction test) or induce spatial anxiety (elevated plus maze test). At a high dose (5 mg·kg-1), MXE induced transient analgesia (tail-flick and hot-plate test), decreased social interaction time (social interaction test) and reduced immobility time while increasing swimming activity (forced swim test), suggesting an antidepressant effect.
Route of Administration: Intraperitoneal
It was investigated the effects of methoxetamine (MXE) on several endpoints using multiple in vitro models. These included rat primary cortical cells, human SH-SY5Y cells, human induced pluripotent stem cell (hiPSC)-derived iCell Neurons, DopaNeurons and astrocyte co-cultures, and human embryonic kidney (HEK293) cells. There were studied effects on several neurotransmitter receptors using single cell intracellular calcium [Ca2+]i imaging, effects on neuronal activity using micro-electrode array (MEA) recordings and effects on human monoamine transporters using a fluorescence-based plate reader assay. In rat primary cortical cells, 10 μM MXE increased the glutamate-evoked increase in [Ca2+]. MXE and ketamine did not affect voltage-gated calcium channels (VGCCs), but inhibited spontaneous neuronal activity (IC50 0.5 μM and 1.2 μM respectively). In human SH-SY5Y cells, 10 μM MXE slightly inhibited the K+- and acetylcholine-evoked increase in [Ca2+]i. In hiPSC-derived iCell (Dopa)Neurons, only the ATP-evoked increase in [Ca2+]i was slightly reduced. Additionally, MXE inhibited spontaneous neuronal activity (IC50 between 10 and 100 μM). Finally, MXE potently inhibits uptake via monoamine transporters (DAT, NET and SERT), with IC50 values in the low micromolar range (33, 20, 2 μM respectively).
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:54:09 UTC 2023
Edited
by admin
on Sat Dec 16 08:54:09 UTC 2023
Record UNII
ZO5ZCE6E12
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Methoxetamine
Common Name English
CYCLOHEXANONE, 2-(ETHYLAMINO)-2-(3-METHOXYPHENYL)-
Systematic Name English
MXE
Common Name English
(±)-2-(3-METHOXYPHENYL)-2-(ETHYLAMINO)CYCLOHEXANONE
Systematic Name English
DEA NO. 7286
Common Name English
2-(ethylamino)-2-(3-methoxyphenyl)cyclohexan-1-one
Systematic Name English
(RS)-2-(3-METHOXYPHENYL)-2-(ETHYLAMINO)CYCLOHEXANONE
Systematic Name English
Classification Tree Code System Code
DEA NO. 7286
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
WIKIPEDIA Designer-drugs-Methoxetamine
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
Code System Code Type Description
SMS_ID
100000166678
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
FDA UNII
ZO5ZCE6E12
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
PUBCHEM
52911279
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
WIKIPEDIA
METHOXETAMINE
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
EVMPD
SUB180905
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
CAS
1239943-76-0
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID30100932
Created by admin on Sat Dec 16 08:54:09 UTC 2023 , Edited by admin on Sat Dec 16 08:54:09 UTC 2023
PRIMARY
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