chemistry

Methoxetamine

Methoxetamine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Methoxetamine rather than just read about it. In short: Methoxetamine (MXE) is a dissociative hallucinogen that has been sold as a designer drug. It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine.

Key takeaways

Methoxetamine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Methoxetamine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Methoxetamine from memory before moving on to harder problems.

Reference excerpt

Methoxetamine (MXE) is a dissociative hallucinogen that has been sold as a designer drug. It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine. MXE is an arylcyclohexylamine. It acts mainly as an NMDA receptor antagonist, similarly to other arylcyclohexylamines like ketamine and PCP.

Recreational use

Effects

MXE is reported to have a similar effect to ketamine. It was often believed to possess opioid properties due to its structural similarity to 3-HO-PCP, but this assumption is not supported by data, which shows insignificant affinity for the μ-opioid receptor by the compound. Recreational use of MXE has been associated with hospitalizations from high and/or combined consumption in the US and UK. Acute reversible cerebellar toxicity has been documented in three cases of hospital admission due to MXE overdose, lasting for between one and four days after exposure. MXE was designed in part in an attempt to avoid the urotoxicity associated with ketamine abuse; it was thought the compound's increased potency and reduced dose would limit the accumulation of urotoxic metabolites in the bladder. Like ketamine, MXE has been found to produce bladder inflammation and fibrosis after high dose chronic administration in mice, although the dosages used were quite large. Reports of urotoxicity in humans have yet to appear in the medical literature.

Pharmacology

Pharmacodynamics

MXE acts mainly as a selective and high-affinity NMDA receptor antagonist, specifically of the dizocilpine (MK-801) site (Ki = 257 nM). It produces ketamine-like effects. In addition to antagonism of the NMDA receptor, MXE has been found to act as a serotonin reuptake inhibitor (Ki = 479 nM; IC50 = 2,400 nM). Conversely, it shows little or no effect on the reuptake of dopamine and norepinephrine (Ki and IC50 > 10,000 nM). Nonetheless, MXE has been found to activate dopaminergic neurotransmission, including in the mesolimbic reward pathway. This is a characteristic that it shares with other NMDA receptor antagonists, including ketamine, PCP, and dizocilpine (MK-801). Animal studies suggest MXE may have rapidly-acting antidepressant effects similar to those of ketamine. A study that assessed binding of MXE at 56 sites including neurotransmitter receptors and transporters found that MXE had Ki values of >10,000 nM for all sites except the dizocilpine site of the NMDA receptor and the serotonin transporter (SERT).

Pharmacokinetics MXE has a longer duration of action than that of ketamine.

Chemistry

MXE is an arylcyclohexylamine and a derivative of eticyclidine (PCE). It can also be thought of as the β-Keto-derivative of 3-methoxyeticyclidine (3-MeO-PCE), or the N-ethyl homologue of methoxmetamine (MXM) and methoxpropamine (MXPr). It is closely related structurally to ketamine, and more distantly to PCP. MXE hydrochloride is soluble in ethanol up to 10 mg/ml at 25 °C.

Detection in body fluids A forensic standard of MXE is available, and the compound has been posted on the Forendex website of potential drugs of abuse.

History The qualitative effects of MXE were first described online in May 2010 and the compound became commercially available on a small scale in September 2010. By November the use and sale of the MXE had increased enough for it to be formally identified by the European Monitoring Centre for Drugs and Drug Addiction. By July 2011, the EMCDDA had identified 58 websites selling the compound at a cost of 145–195 euros for 10 grams.

Society and culture

Media coverage Mixmag reported in January 2012, that people in the dance music and clubbing community have given MXE the slang name 'roflcoptr'. Vice commented that it was likely that the phrase will only be used by "the same politicians, parents and journalists" who called mephedrone 'meow meow'. After being called mexxy in UK Home Office press releases, the media adopted the name. A literature review was published in March 2012 which looked at scientific literature and information on the web. It concluded that "the online availability of information on novel psychoactive drugs, such as MXE, may constitute a pressing public health challenge. Better international collaboration levels and novel forms of intervention are necessary to tackle this fast-growing phenomenon."

Legal status

Brazil MXE became classified as a narcotic in Brazil in February 2014.

Canada As of January 2011 MXE is a controlled substance in Canada.

China As of October 2015 MXE is a controlled substance in China.

European Union On 16 June 2014, the European Commission proposed that MXE be banned across the European Union, subjecting those in violation to criminal sanctions. This is following the procedure for risk-assessment and control of new psychoactive substances set up by the council: Decision 2005/387/JHA.

Finland Scheduled in the "government decree on narcotic substances, preparations and plants" and is hence illegal.

Israel MXE became classified as an illegal narcotic in Israel in May 2012.

Japan MXE became a controlled substance in Japan from 1 July 2012, by amendment to the Pharmaceutical Affairs Law.

Poland MXE is a controlled substance (group II-P) making it illegal to produce, sell or possess in The Republic of Poland as of 1 July 2015.

Russia MXE has been a controlled substance in Russia since October 2011.

Sweden MXE became classified as a narcotic in Sweden in late February 2012.

Switzerland MXE has been illegal in Switzerland since December 2011.

… excerpt ends here. Continue reading the full article.

Illustrations

Worked examples

Example 1 — a first encounter with Methoxetamine

Start with the simplest possible case. Write down what Methoxetamine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Methoxetamine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Methoxetamine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Methoxetamine

In research: Methoxetamine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Methoxetamine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Methoxetamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics 3-Methoxyphenyl compounds, Arylcyclohexylamines, Designer drugs, so understanding it makes those chapters shorter.
In everyday life: Look for Methoxetamine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Methoxetamine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Methoxetamine means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Methoxetamine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methoxetamine in simple terms?

Why does Methoxetamine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Methoxetamine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Methoxetamine.