Chemistry:5-MeO-EiPT

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5-MeO-EiPT, also known as 5-methoxy-N-ethyl-N-isopropyltryptamine, is a psychedelic drug of the tryptamine family which has been sold online as a designer drug.[1][2][3][4]

Use and effects

5-MeO-EiPT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[5][6] When subsequently asked about 5-MeO-EiPT, Shulgin said that he never got around to making or exploring it and that its dose, duration, and effects were unknown.[6] In any case, 5-MeO-EiPT has been used as a novel recreational designer drug.[6][4]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-EiPT acts as a potent full agonist of the serotonin 5-HT2A receptor.[3] It also shows high affinity for the serotonin 5-HT1A receptor and interacts very weakly with the serotonin transporter (SERT).[3] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[3] However, it produces a rather weak head-twitch response, suggesting that it might have reduced hallucinogenic effects relative to other psychedelic tryptamines or might be non-hallucinogenic.[3] The serotonin 5-HT1A receptor antagonist WAY-100635 augmented the head-twitch response induced by 5-MeO-EiPT in rodents.[3] The drug also produces hypothermia and hypolocomotion in rodents.[3]

Chemistry

Analogues

Analogues of 5-MeO-EiPT include ethylisopropyltryptamine (EiPT), 4-HO-EiPT (ethiprocin), 4-AcO-EiPT (ethipracetin), 5-MeO-DMT, 5-MeO-DET, 5-MeO-DPT, 5-MeO-DiPT, 5-MeO-DALT, 5-MeO-MET, 5-MeO-MPT, 5-MeO-MiPT, 5-MeO-MsBT, 5-MeO-EPT, 5-MeO-PiPT, and 5-MeO-iPALT (ASR-3001), among others.[5]

History

5-MeO-EiPT was first described by Alexander Shulgin by 2002.[6]

Society and culture

5-MeO-EiPT is illegal in Japan.[7] 5-MeO-EiPT is illegal in Italy.[8] Sweden's public health agency suggested classifying 5-MeO-EiPT as a hazardous substance, on May 15, 2019.[9][10]

See also

References

  1. ↑ "5-MeO-EiPT". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/17299. 
  2. ↑ "Simultaneous determination of tryptamine analogues in designer drugs using gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry". Forensic Toxicology 32 (1): 154–161. January 2014. doi:10.1007/s11419-013-0208-3. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry 29 (8): 2346–2358. August 2024. doi:10.1038/s41380-024-02506-8. PMID 38486047. 
  4. ↑ 4.0 4.1 https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2014
  5. ↑ 5.0 5.1 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  6. ↑ 6.0 6.1 6.2 6.3 "Ask Dr. Shulgin Online February 27, 2002". 27 February 2002. https://www.cognitiveliberty.org/ccle1/shulgin/adsarchive/5meo.htm. "[Derek:] A company that sells chemical novelties has recently begun selling something that they call 5-methoxy-N-ethyl-N-isopropyltryptamine [(5-MeO-EiPT)]. I have searched the Internet, TIHKAL, and other literature for it. I can't find mention of it anywhere. Is it psychoactive? If so what are the effects and what's the dose range? [...] [Shulgin:] the N-ethyl is half-way between [5-MeO-MiPT and 5-MeO-DiPT] and I never did get around to making it. But apparently someone else did. My gut feeling would be to call it 5-MeO-EIPT. But as to predicting the active dosage range and its effects, I would be conservative and cautious." 
  7. ↑ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (in ja). 厚生労働省. 16 September 2015. http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf. 
  8. ↑ "Tabella 1 Sostanze Stupefacenti" (in it). Governo Italiano. March 2017. http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf. 
  9. ↑ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 15 May 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/maj/folkhalsomyndigheten-foreslar-att-20-amnen-klassas-som-narkotika-eller-halsofarlig-vara/. 
  10. ↑ "5-MeO-EIPT" (in ru). https://aipsin.com/newsubstance/137/. 



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