4-AcO-DiPT
Verifiedfieldsverified
Verifiedrevid477345095
Drug name4-AcO-DiPT
Width200px
Width 2200px
Routes of administrationOral[1]
ClassNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Atc prefixNone
Cas number936015-60-0
Pubchem24801868
Chemspiderid21106240
UniiXV36ISE3YQ
Synonyms4-Acetoxy-DiPT; 4-Acetoxy-N,N-diisopropyltryptamine
Iupac name3-{2-[di(propan-2-yl)amino]ethyl}-1H-indol-4-yl acetate
C18
H26
N2
O2
SmilesCC(C)N(CCc1c[nH]c2c1c(ccc2)OC(=O)C)C(C)C
Stdinchi1S/C18H26N2O2/c1-12(2)20(13(3)4)10-9-15-11-19-16-7-6-8-17(18(15)16)22-14(5)21/h6-8,11-13,19H,9-10H2,1-5H3
StdinchikeyZPAOVGZYDSXCPK-UHFFFAOYSA-N

4-AcO-DiPT, also known as 4-acetoxy-N,N-diisopropyltryptamine or as ipracetin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to 4-AcO-DMT (psilacetin).[1][2] It is taken orally.[1]

The drug is thought to likely be a prodrug of 4-HO-DiPT, which acts as a non-selective serotonin receptor agonist including of the serotonin 5-HT2A receptor.[3][2] It produces psychedelic-like effects in animals.[2]

4-AcO-DiPT was first described in the literature by 1999.[4][1] It was encountered as a novel designer drug in 2005.[2][5][6]

Use and effects

See also: 4-HO-DiPT#Use and effects

According to Alexander Shulgin in a 2003 literature review, the dose range of 4-AcO-DiPT is 6 to 10 mg orally.[1] For comparison, the dose range of 4-HO-DiPT is listed as 15 to 20 mg in the same review.[1] Other reports of the properties and effects of 4-AcO-DiPT in humans have also been reported in The Entheogen Review.[4]

Interactions

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

Pharmacology

Pharmacodynamics

4-AcO-DiPT is thought to be likely to function as prodrug of 4-HO-DiPT, although pharmacokinetic studies are still needed to confirm this.[3][2] It acts as a serotonin 5-HT2 receptor agonist, albeit with greatly reduced potency relative to 4-HO-DiPT.[2] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2]

Chemistry

4-AcO-DiPT is a tryptamine and is structurally similar to 4-HO-DiPT, psilocin (4-HO-DMT), and 4-AcO-DMT (psilacetin).[1][2]

Analogues

Analogues of 4-AcO-DiPT include diisopropyltryptamine (DiPT), 4-HO-DiPT (iprocin), 4-PrO-DiPT, luvesilocin (4-GO-DiPT), 4-AcO-DMT (psilacetin), 4-AcO-DET (ethacetin), 4-AcO-DPT (depracetin), and 4-AcO-DALT (dalcetin), among others.

History

4-AcO-DiPT was first described in the literature by 1999.[4] Subsequently, it was described by Alexander Shulgin in 2003.[1] The drug was encountered as a novel designer drug in 2005.[2][5][6]

Society and culture

Denmark

4-AcO-DiPT is added to the list of Schedule B controlled substances.[7]

Japan

4-AcO-DiPT is a controlled substance in Japan.[8]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-AcO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 4-acetoxi-N,N-diisopropyltryptamin (4-AcO-DIPT), making it illegal to sell or possess.[9]

United States

4-AcO-DiPT is an unscheduled substance in the United States. Due to similarities to other scheduled tryptamines, such as diethyltryptamine and psilocin, possession may be prosecuted under the Federal Analog Act in the United States.

See also

References

  1. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
  2. ^ Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. PMID 33860183
  3. ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875
  4. ^ Toad (1999). "4-Acetoxy-DiPT Primer". The Entheogen Review. 8 (4): 126–131. ISSN 1066-1913
  5. ^ https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  6. ^ Rodriguez-Cruz, S. E. (2005). Analysis and Characterization of Designer Tryptamines using Electrospray Ionization Mass Spectrometry (ESI-MS). Microgram, 3(3–4), 107–129. https://forendex.southernforensic.org/uploads/references/MicrogramJournal/3.3-4.107.129.pdf
  7. ^ "Bekendtgørelse om euforiserende stoffer - retsinformation.dk"
  8. ^ "指定薬物一覧｜厚生労働省". Retrieved 23 December 2011.
  9. ^ "1Svensk författningssamling". www.notisum.se. 3 February 2005. Archived from the original on 2013-09-29. Retrieved 2020-03-24.