5-MeO-MiPT

5-MeO-MiPT
Legal status
Legal status
Identifiers
IUPAC name
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.223.426
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Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
SMILES
  • O(c1cc2c(cc1)[nH]cc2CCN(C(C)C)C)C
InChI
  • InChI=1S/C15H22N2O/c1-11(2)17(3)8-7-12-10-16-15-6-5-13(18-4)9-14(12)15/h5-6,9-11,16H,7-8H2,1-4H3 checkY
  • Key:HEDOODBJFVUQMS-UHFFFAOYSA-N checkY
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Two tablets of 5-MeO-MiPT

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

Chemistry

5-MeO-MiPT is in a class of compounds commonly known as tryptamines, and is the N-methyl-N-isopropyl homologue of the psychedelic, 5-MeO-DMT. The full name of the chemical is 5-methoxy-N-methyl-N-isopropyltryptamine.

5-MeO-MiPT causes the ehrlich reagent to turn purple then fade to faint blue. It causes the marquis reagent to go yellow through to black.[1]

Effects

This is an analogue of the more popular drug 5-MeO-DiPT (nicknamed "foxy methoxy") and has the nickname "moxy". Some users report the tactile effects of 5-MeO-DiPT without some of the unwanted side effects. At higher doses it becomes much more psychedelic sometimes being compared to 5-MeO-DMT. But at doses of 4-10 milligrams users find 5-MeO-MiPT to be a very euphoric and tactile chemical.[2] Its energetic effects can be very strong at high doses, increasing normal heart rate considerably. Sounds can be amplified in perception to a point where synesthetic effects ("touching or/and tasting sounds") occur.

Pharmacodynamics

Binding Sites Binding Affinity Ki (μM)[3]
5-HT1A 0.058
5-HT2A 0.163
5-HT2C 1.3
D1 >25
D2 >25
D3 >25
α1A >12
α2A 5.3
TAAR1 >15
H1 3.9
SERT 3.3
DAT >26
NET >22

Dosage

Based on many anecdotal reports,[4][5] dosages can be classified as follows:

Smoked Oral
Threshold 5 mg 3 mg
Light 5 - 10 mg 3 - 7 mg
Common 10 - 15 mg 7 - 15 mg
Strong 15 - 20 mg 15 - 20 mg
Heavy 20 mg + 20 mg +

Pharmacology

The mechanism that produces the hallucinogenic and entheogenic effects of 5-MeO-MiPT is thought to result primarily from 5-HT2A receptor agonism, although additional mechanisms of action such as inhibition of MAO may be involved also.[6][7] While 5-MeO-MiPT binds most strongly to 5-HT1A receptors, it also shows fairly strong binding affinity to the SERT and NET, thereby acting as a moderately potent serotonin-norepinephrine reuptake inhibitor.[8] These mechanisms may help explain why there are many anecdotal reports of anti-depressant and anxiolytic effects from modest doses of this compound. For example, SNRIs such as venlafaxine are commonly prescribed to treat depression, and the 5-HT1A agonist buspirone is prescribed primarily for treatment of anxiety.

Reagent Results

Exposing compounds to the reagents gives a colour change which is indicative of the compound under test. The following test results are from protestkit.

5-MeO-MiPT Marquis Mecke Mandelin Liebermann Ehrlich Hofmann Simon’s
Freebase Orange to brown Orange red Deep greenish brown Unknown Purple No reaction No reaction
HCl Orange to brown Red to brown Greenish brown Brown Violet to purple Green Unknown

Dangers

The toxicity of 5-MeO-MiPT is not known. There is no known documentation of death attributed to the use of 5-MeO-MiPT alone.

Canada

5-MeO-MiPT is not scheduled in Canada.

China

As of October 2015 5-MeO-MiPT is a controlled substance in China.[9]

Luxembourg

In Luxembourg, 5-MeO-MiPT is not cited in the list of prohibited substances.[10] Therefore, it is still a legal substance.

United Kingdom

5-MeO-MiPT is a Class A drug in the United Kingdom as are most ethers of ring-hydroxy tryptamines.

United States

5-MeO-MiPT is unscheduled at the federal level in the United States,[11] but it could be considered an analog of 5-MeO-DiPT, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Florida

"5-Methoxy-N-methyl-N-isopropyltryptamine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in the state of Florida.[12]

See also

References

  1. ↑ Spratley, Trinette (2004). "Analytical Profiles for Five "Designer" Tryptamines" (PDF). Microgram Journal. 3 (1–2): 55. Retrieved 2013-10-09.
  2. ↑ Carpenter, David E. (2022-01-25). "DEA Proposes Adding Five Psychedelic Compounds to Schedule 1". Lucid News. Retrieved 2022-01-26.
  3. ↑ Rickli A.; Moning O.D.; Hoener M.C.; Liechti M.E. (2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–37. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487. S2CID 6685927.
  4. ↑ "Erowid Online Books : "TIHKAL" - #40 5-MEO-MIPT". www.erowid.org. Retrieved 2021-06-01.
  5. ↑ "5-MeO-MIPT (also 5-Methoxy-N,N-Methylisopropyltryptamine) : Erowid Exp: Main Index". www.erowid.org. Retrieved 2021-06-01.
  6. ↑ Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry. 28 (7): 892–6. doi:10.1021/jm00145a007. PMID 4009612.
  7. ↑ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  8. ↑ Ray, T. S. (2010). "Psychedelics and the Human Receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
  9. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  10. ↑ Loi du 19 février 1973 concernant la vente de substances médicamenteuses et la lutte contre la toxicomanie.
  11. ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  12. ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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