| Stereochemistry | RACEMIC |
| Molecular Formula | C15H21NO2.ClH |
| Molecular Weight | 283.794 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCNC1(CCCCC1=O)C2=CC=CC(OC)=C2
InChI
InChIKey=FJNRBMKLTGCSRN-UHFFFAOYSA-N
InChI=1S/C15H21NO2.ClH/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;1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H21NO2 |
| Molecular Weight | 247.3327 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| 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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 259.0 nM [Ki] | |||
| 481.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
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).
