5-MeO-MiPT

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5-MeO-MiPT is a psychedelic in the tryptamine class. It’s uncommon relative to LSD and psilocin, but it has been used for a couple of decades. It’s not a very visual substance at common doses. Instead, it’s known for producing greater tactile, bodily, and sexual effects than other psychedelics.

It’s part of the research chemical market and has been sold as itself and as a component of branded products.


5-MeO-MiPT = 5-Methoxy-N-methyl-N-isopropyltryptamine; Moxy

PubChem: 2763156

Molecular formula:  C15H22N2O

Molecular weight: 246.354 g/mol

IUPAC: N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine


Dose

Oral

Light: 1 – 3 mg

Common: 3 – 8 mg

Strong: 8 – 12 mg

Inhalation

Common: 10 – 20 mg


The dose-response curve is steep, meaning a small increase can yield a substantial change in intensity. A couple milligrams may be all it takes to make an experience unpleasant and overwhelming. Since the drug is quite potent and responses vary between people, users should be careful with their dosing and initially take a light amount to evaluate their response.

A scale is needed for proper dosing, though typical milligram scales still won’t be ideal for measuring. Therefore, a scale should be used alongside volumetric dosing.

While some people find under 10 mg to be underwhelming, others find the same amount or less to be very uncomfortable.

Doses under 10 mg may be preferred for mood effects and physical euphoria, while higher doses are more likely to offer notable psychedelic effects.


Timeline

Oral

Total: 3 – 6 hours

Onset: 00:15 – 00:45 (the onset is usually pretty fast)

It can produce an altered mental state and lingering insomnia for a few hours beyond the main duration.

Both immediately after the main effects end and in the following days it can produce an afterglow. Short-lasting positive after effects are more common than having it trigger depression or anxiety, though for many people the after effect period is neutral.


Experience Reports

Erowid


Effects

Psychological/Cognitive

Overall, 5-MeO-MiPT is pretty unique among the psychedelics and has an effect profile that pulls from multiple drug classes.

It’s usually stimulating rather than sedating, though the stimulation is more physical than mental. Because of this, some users find engaging in activities like hiking or dancing is more comfortable than sitting still. Having an outlet for the physical energy may help to minimize jitteriness and a feeling of unease, but it’s also the case that other users dislike being active on it.

At common doses it’s not a very confusing or insightful substance, but it can have a moderate impact on your thinking and creativity. It’s been called a “shallower” psychedelic for this reason, though that shouldn’t be taken to mean it can’t trigger a distressing or useful experience.

Feelings of dissociation and dreaminess are often reported.

At high doses confusion and generally strange experiences are much more common. There are a few reports of people becoming unresponsive or having trouble talking, mainly at high doses.

It’s commonly promoted as a tryptamine alternative to MDMA, but this is almost always an exaggeration. There are some elements, like increased appreciation of others and pleasant tactile sensations, that could be comparable, but it’s not a full entactogen and has a much less reliable impact on mood and outlook.

The visual effects can be substantial at high doses, but at common amounts they’re quite limited. You can still receive color enhancement, changes to depth perception, and some movement like breathing, but very strong distortions or hallucinations are rare at these doses. People who are primarily interested in visual effects aren’t going to be very interested in it unless they can handle higher doses, which will often be physically unpleasant.

Because a minority of people do get substantial visuals while others never get them even at high doses, it’s been hypothesized that a metabolic difference could be at aply. There’s no proof of this, but it is true that the effects, visual and otherwise, vary a lot between people, as is often the case with psychedelics in general.

Sexual effects are attributed to the drug more often than with most psychedelics. Tactile enhancement combines with a higher sex drive and lower inhibition. It’s also easier for a male to get an erection than it is with entactogens, which also enhance tactile sensation. Orgasms can be more intense as well. Many reports describe sexual thoughts or sensations suddenly manifesting under the influence, even in situations that aren’t conducive to sexual activity. Those feelings can be ignored if needed and they don’t occur for everyone.

Music is often more impactful.  Users report noticing aspects of songs that are normally ignored and music may also trigger physical sensations or visual distortions, more often with eyes closed. Music and sex are two of the main cases where people, at least those who respond well to the drug, will choose it in place of other psychedelics. Actual auditory distortions can be present as well, though they’re not always positive.

Because it doesn’t have a significant headspace and usually doesn’t produce strong visuals, the tactile and other sensory effects are some of the main positive aspects of the drug. If those aren’t present or sufficiently enjoyable, you may be disappointed. But when the experience is positive it can be one of the most enjoyable psychedelics.

Usually appetite is lowered, but the taste of food may be enhanced.

Some users report finding things more humorous than usual.


Physical/Bodily

Body load is very common and can ruin the experience when it’s significant. It can include nausea, over-excitation, vomiting, chills, lightheadedness, bloating, shivering, sensations of heat, tension, and headache. Feeling like you can’t breathe properly or like you’re experiencing a lot of cardiovascular stress can contribute to anxiety and panic.

These physical symptoms underlie a lot of the anxiogenic potential of the drug and are responsible for a large portion of the negative experiences. In the absence of those properties it doesn’t tend to cause much anxiety on its own. People are much more likely to become stressed due to feeling uncomfortable and being concerned about their physical safety.

It’s not an exaggeration to say it can feel horrible to an extent that’s largely not seen with other psychedelics. This isn’t the typical experience, but it’s a possibility, and it’s one of the reasons you need to be careful with your dosing.

On average, the come up is more uncomfortable than the peak and comedown.

Despite it having a notable body load, it can also come with physical euphoria and other positive bodily effects, sometimes concurrently with the aforementioned negatives. Tactile enhancement, such as things feeling softer or enjoying contact with other people, is very common. And even in the absence of external input, it can produce rushes of pleasurable sensations in the body. This same effect might be the cause of unpleasant coldness and heat for those who are perceiving the effect differently.


Combinations

Some people have reported successfully combining it with entactogens or psychedelics, though the reports vary, especially for entactogens. The safety of using 5-MeO-MiPT with entactogens is a bit unclear due to an incomplete understanding of its pharmacology, so it’s best to avoid using them together.

Combining psychedelics, though sometimes useful, less predictably raises the chance of confusion, anxiety, and other problematic mental effects. It’s best to avoid that combination.


Chemistry

5-MeO-MiPT is a substituted tryptamine and an analog of 5-MeO-DiPT. The 5-methoxy substitution, in addition to causing changes to the effects, increases the potency of the substance compared to its parent compound, MiPT.


Pharmacology

Like with DiPT, the 5-MeO substitution produces an increase in 5-HT2A affinity and activation potency. Early research was interpreted by some to mean it has substantial serotonin reuptake inhibition, but the research showed its IC50 value was over 6 μM, which isn’t very high (Nagai, 2007).

More recent research supports 5-MeO-MiPT primarily being a serotonin receptor agonist. It can activate 5-HT2A (shown by intracellular calcium increase) with an ED50 of 7.82 nM or 566 nM if looking at 5-HT2A beta-arrestin recruitment, which involves another signalling pathway (Blough, 2014). Blough (2014) showed it had no reuptake inhibition at SERT, NET, or DAT at up to 10 μM (10,000 nM).

Other studies have similarly shown the drug should be classified as a serotonin receptor agonist, much like other psychedelics (Ray, 2010; Rickli, 2016). The different effect profile, such as some entactogen-like mood states and tactile enhancement, doesn’t seem to be coming from monoamine release or reuptake inhibition.

Papers

(Rickli, 2016) – It’s mainly a serotonin receptor agonist with minimal monoamine transporter activity.

  • Human HEK 294 cells expressing human receptors and transporters were used, with the exception of the TAAR1 interaction section.
  • For the 5-HT2A activation assay, intracellular calcium was measured, which rises with the increase in IP3 via the PLC signalling pathway.
  • Results
    • Serotonin receptor interactions
      • 5-HT1A
        • Ki (μM): 0.058
      • 5-HT2A
        • Ki (μM): 0.163
        • EC50 (μM): 0.023
        • Max efficacy: 83%
      • 5-HT2B
        • EC50 (μM): 1.5
        • Max efficacy: 12%
      • 5-HT2C
        • Ki (μM): 1.3
    • Monoamine transporter and receptor binding (in μM)
      • NET: Over 22
      • DAT: Over 26
      • SERT: 3.3
      • α1A: Over 12
      • α2A: 5.3
      • D1: Over 25
      • D2: Over 25
      • D3: Over 25
  • H1: 3.9
  • TAAR1rat: Over 15
  • TAAR1mouse: Over 15
  • Monoamine transporter inhibition (IC50 values in μM)
    • NET: 84
    • DAT: Over 100
    • SERT: 22
  • No significant monoamine release was seen with a high 100 μM concentration.
  • COI/Funding: Author is an employee of Hoffman-La Roche. This work was supported by the Federal Office of Public Health (No.13.006497) and Translational Medicine Hub Innovation Fund of F. Hoffmann-La Roche and the University of Basel.

(Blough, 2014) – It primarily affects 5-HT2A and lacks monoamine transporter effects.

  • Cells expressing human receptors were studied in vitro.
  • Reuptake inhibition (IC50 values in nM)
    • DAT: Over 10,000
    • SERT: Over 10,000
    • NETL: Over 10,000
  • 5-HT2A activation (intracellular calcium; in nM)
    • EC50: 7.82
    • Emax: 101%
  • 5-HT2A beta-arrestin recruitment
    • EC50: 566 nM
    • Emax: 82%
  • 5-HT1A activation
    • EC50: Over 10,000
  • COI: None
    • NIDA provided financial support, as did the Intramural Research Program, NIDA, NIH, and DHHS.

(Ray, 2010) – Its greatest activity is at serotonin receptors, not SERT

  • Data from the Psychoactive Drugs Screening Program. Affinity values were adjusted via a log transformation so that higher values equal higher affinity. Each unit of pKi value represents one order of magnitude of Ki value.
  • The highest affinity target for each drug is represented by 4. Affinities too low to be measured are shown as 0.
  • This normalization method excludes raw potency and allows for an easier comparison of effects between targets.
  • Results
    • 5-HT1A: 4.00
    • 5-HT7: 3.79
    • 5-HT1D: 3.74
    • 5-Ht2B: 3.32
    • 5-HT6: 2.98
    • α2A: 2.85
    • 5-HT1B: 2.61
    • 5-HT2A: 2.44
    • α2C: 2.29
    • Imidazoline 1: 2.15
    • Sigma2: 2.13
    • 5-HT5A: 1.86
    • α2B: 1.86
    • 5-HT2C: 1.75
    • D3: 1.70
    • 5-HT1E: 1.55
    • H1: 1.41
    • D4: 1.29
    • SERT: 1.28
    • 0.00 for all: D2, α1B, D5, D1, beta-2, NET, DAT, Sigma1, Beta1, DOR, KOR, MOR, M1, M2, M3, M4, M5, α1A, H2, CB2, NMDA, Ca+ channel
  • COI: None

(Nonaka, 2007) – It activates GPCRs, which would include serotonin receptors.

  • Data based on binding in rat brain membranes.
    • The study measured labeled GTPyS binding, which indicates GPCR activation.
  • Emax for 5-MeO-MiPT: 35.6%
  • % of serotonin’s max: 68%
  • COI: Not reported

(Nagai, 2007) – Inhibition of serotonin reuptake was seen, though it wasn’t very potent.

  • Synaptosomes prepared from rat striatum and cerebral cortex
  • Results
    • Reuptake (IC50 values in nM)
      • DAT: No effect
      • SERT: 6,400 nM
      • NET: 25,999 nM
    • No impact on monoamine release was observed
  • COI: Not Reported

(Repke, 1985) – The first paper about 5-MeO-MiPT. It describes the drug’s activity in humans.

  • Data from 5 human subjects and 12 trials.
  • Effective dose: 5 mg or 0.07 mg/kg
  • Onset: 9 – 16 min
  • Duration: 3 – 3.2 hours
  • “It has an extremely rapid onset and causes a general heightening of awareness along with amphetamine-like central stimulation. Like with MiPT, it does not produce the intense visual phenomena associated with 4-HO-MiPT.”
  • COI: Not reported

Pharmacokinetics

5-MeO-MiPT is metabolized via multiple routes, yielding 5-MeO-NiPT, 5-HO-MiPT, HO-5-MeO-MiPT, 5-MeO-MiPT-N-oxide, and others (Grafinger, 2017; Katagi, 2010).


Tolerance

Few reports characterizing its tolerance are available, but it seems to produce less tolerance than the average psychedelic. There are some reports of it being successfully used on subsequent days.

Once tolerance is present it should largely go away within a week.


History

1980s

The first paper on 5-MeO-MiPT was published in 1985 by David Repke, Douglas Grotjahn, and Alexander Shulgin.

2000s

Most of its use has occurred since the early to mid-2000s. It’s been sold through the research chemical market either as itself or as a component of branded “legal high” products.

2005 – 2007

(Takahashi, 2008 ) – A Japanese paper described its presence in products purchased from stores and online between 2005 and 2007. Of the 178 products tested, 30 contained 5-MeO-MiPT.

2013 – 2015

(Odoardi, 2016) – The contents of novel psychoactive substance (NPS) samples from 162 seizures in Italy were analyzed. One of those samples contained 5-MeO-MiPT, but it was present alongside methylone, ethylone, methedrone, 4-FA, and 5-MeO-DALT.

(Backberg, 2015) – Sweden’s STRIDA project was notified of 1243 cases of suspected NPS intoxication. Of those, the 59 cases testing positive for 3-MeO-PCP and/or 4-MeO-PCP were analyzed further. 52 showed signs of polydrug use, 17 of which involved 5-MeO-MiPT.

As of 2018

It is still sold through the research chemical market and through the dark web, but it isn’t one of the top psychedelics. It’s usually not explicitly illegal.


Legality

United States

Unscheduled, but it could be treated as an illicit analog of 5-MeO-DiPT.

It is scheduled in Florida (Schedule 1), Louisiana (Schedule 1), and Minnesota (Schedule 1).

Australia

It could be treated as an illicit analog.

Canada

Unscheduled

UK

Class A


Safety

Given the lack of information about the drug, it should be taken at common doses, infrequently, and without combinations.

Because of its apparent pharmacology and effects, it’s reasonable to assume agitation, confusion, panic, tachycardia, hypertension, hyperthermia, and temporary psychosis are possible outcomes. A few reports of toxicity support its ability to cause confusion and temporary psychosis.

The chance of negative effects can be reduced by taking common doses.

Risky Combinations (list is not exhaustive)

Stimulants, other psychedelics, MAOIs, and tramadol.

Adverse effect reports

(Grafinger, 2017) – Confusion and agitation after confirmed use.

  • 32-year-old male. Found standing naked and without orientation in the street.
    • He had several abrasions all over his body. He reacted with agitation and aggression when approached by police, who were called to the seen by a friend who reported the male had taken an “LSD-like substance.”
  • A blood sample was collected 1 hour after and a urine sample 2 hours after the police appeared on the scene.
  • Toxicology confirmed 5-MeO-MiPT use
    • Blood: 160 ng/mL
    • Urine: 3380 ng/mL

(Shimizu, 2007) – Combined intoxication with methylone and 5-MeO-MiPT. Confusion and cardiovascular stimulation were observed.

  • 27-year-old male. Took approximately 200 mg (oral) of a drug believed to be methylone. Then he reported nausea and shouted with agitation, then fell down on the floor and was crying.
  • At the ED, he stared incoherently and was silent in confusion, though he also exhibited sudden and brief psychomotor excitement and shouted for no reason.
    • Temp 37.8°C, HR 150, BP 144/81, dilated pupils and sweating.
  • Continued to exhibit symptoms of psychomotor excitement 3.5 hours after ingestion. Symptoms later resolved and were seemingly helped by risperidone.
  • The remaining powder was tested.
    • The analysis indicated it was ~60% methylone and ~38% 5-MeO-MiPT, meaning an estimated 120 mg methylone and 76 mg 5-MeO-MiPT may have been taken.
  • COI: Not reported

(Itokawa, 2007) – Confusional state caused by 5-MeO-MiPT and 5-MeO-DiPT.

  • 23-year-old female. She presented 6.5 hours after taking a liquid called “Ecstasy Liquid 2 Natural Type” to enhance sexual performance.
    • She became nauseous after taking it and vomited. Though she also took Love Boll (half of a tablet) about 1 hr after the liquid. Both drugs were obtained by her partner on the street.
  • 2 hours after administration, she was speaking and repeating the same content without responding to her boyfriend. She also displayed excited and disorganized behavior. She walked around irritably, threw things, and shouted.
  • Examination at hospital
    • Not alert or oriented. BP of 114/83. No motor deficit, tremor, or ataxia.
    • Did not answer any questions. She was smirking and looking around restlessly.
  • She was able to answer some questions 8 hrs after taking the liquid, but she was still confused about the date and season.
    • Incoherence and perplexity. Anterograde amnesia with ambiguous memory post-ingestion. Denied experiencing any auditory or visual hallucinations or delusions.
  • Urine collected 8 hr post-ingestion
    • Toxicology showed both 5-MeO-DiPT and 5-MeO-MiPT.
  • The authors of the paper had previously detected 5-MeO-DiPT from Love Boll and 5-MeO-MiPT from Ecstasy Liquid 2.
  • COI: This work was supported by a Grant from the Ministry of Health, Labor and Welfare (16242701).

(Matsumoto, 2006) – Link, along with 5-MeO-DiPT, to psychotic effects and a murder.

  • 22-year-old male purchased three designer drugs online, “Foxy” “Wild Game” and “Mipty.”
    • He took Wild Game and Mipty together at an unknown dose along with his girlfriend.
  • Soon after he had palpitations, nausea, and was fearing a bad trip, though he was still able to recognize his girlfriend.
  • About 1.5 hours after ingestion, he perceived things delusionally, thought his surroundings were conveying ominous warnings, spiritual meanings, and important revelations.
    • Sensory distortion, visual illusion, and intermittent loss of consciousness were reported.
  • Police officers found him naked and bloody at midnight near his apartment around 3 hours after intake. He was markedly confused and incoherent.
    • The police reported he killed his girlfriend just before the arrest.
    • A container labeled “Mipty” was found in his room. Analysis confirmed the presence of 5-MeO-DiPT and 5-MeO-MiPT. Both substances were also found in his urine and in his girlfriend.
  • Because Mipty contained both drugs and Wild Game was shown to just contain 5-MeO-DiPT, it’s possible the 5-MeO-DiPT exposure was greater.
  • COI: Not reported

References

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