5-MeO-EiPT

5-MeO-EiPT
Clinical data
Other names5-Methoxy-N-ethyl-N-isopropyltryptamine
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • N-ethyl-5-methoxy-N-(1-methylethyl)-1H-indole-3-ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H24N2O
Molar mass260.381 g·mol−1
3D model (JSmol)
  • CC(C)N(CC)CCC1=CNC2=CC=C(OC)C=C21
  • InChI=1S/C16H24N2O/c1-5-18(12(2)3)9-8-13-11-17-16-7-6-14(19-4)10-15(13)16/h6-7,10-12,17H,5,8-9H2,1-4H3
  • Key:VVEQXDHSGNBFLZ-UHFFFAOYSA-N

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 or 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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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 (eiprocin), 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-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]

See also

References

  1. ^ "5-MeO-EiPT". Cayman Chemical. Retrieved 21 July 2015.
  2. ^ Nakazono Y, Tsujikawa K, Kuwayama K, Kanamori T, Iwata YT, Miyamoto K, Kasuya F, Inoue H (January 2014). "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. doi:10.1007/s11419-013-0208-3. S2CID 25134125.
  3. ^ a b c d e f g Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.
  4. ^ a b https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2014
  5. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  6. ^ a b c d "Ask Dr. Shulgin Online February 27, 2002". keeping freedom in mind -. 27 February 2002. Retrieved 12 November 2025. [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）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 8 October 2015.
  8. ^ "Tabella 1 Sostanze Stupefacenti" (PDF) (in Italian). Governo Italiano. March 2017. Archived from the original (PDF) on 6 February 2016. Retrieved 27 March 2017.
  9. ^ "Folkhälsomyndigheten föreslår att 20 ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 15 May 2019. Archived from the original on 20 October 2021. Retrieved 11 November 2019.
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