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4-PrO-DMT

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4-PrO-DMT
Clinical data
Other names4-Propanoyloxy dmt
Identifiers
  • [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] propanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H20N2O2
Molar mass260.337 g·mol−1
3D model (JSmol)
  • CCC(=O)OC1=CC=CC2=C1C(=CN2)CCN(C)C
  • InChI=1S/C15H20N2O2/c1-4-14(18)19-13-7-5-6-12-15(13)11(10-16-12)8-9-17(2)3/h5-7,10,16H,4,8-9H2,1-3H3
  • Key:KUOGXPDQORRHED-UHFFFAOYSA-N

4-Propionoxy-N,N-dimethyltryptamine (4-PrO-DMT, or O-Propionylpsilocin) is a synthetic psychedelic drug from the tryptamine family with psychedelic effects, and is believed to act as a prodrug for psilocin.[1] It produces a head-twitch response in mice.[1] It has been sold online as a designer drug since May 2019. It was first identified as a new psychoactive substance in Sweden, in July 2019.[2] A number of related derivatives have been synthesized as prodrugs of psilocin for medical applications.[3]

Recreational use

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4-PrO-DMT Crystals
4-PrO-DMT Crystals.

Dosage

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4-PrO-DMT is reported to be orally psychoactive substance and while dosage effects have been studied in mice, its effects and longevity on humans has not been formally studied. The effects of 4-PrO-DMT are similar to those of psilocin (4-HO-DMT), as it acts as a prodrug.[1][4]

Toxicity

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Very little data about the toxicity or pharmacology of 4-PrO-DMT is known. Its chemical structure and pharmacological activity are similar to psilacetin, a compound which isn't associated with compulsive use or physical dependence. However, due to lack of research and data, it cannot be definitively concluded that its pharmacological actions in the human body do not differ from those of psilacetin. To date, there have been no reported deaths from 4-PrO-DMT.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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Psilocin at molecular targets
Target Affinity (Ki, nM)
5-HT1A 49–567 (Ki)
853–>3,160 (EC50Tooltip half-maximal effective concentration)
ND (EmaxTooltip maximal efficacy)
5-HT1B 31–305
5-HT1D 19–36
5-HT1E 44–52
5-HT1F ND
5-HT2A 6.0–340 (Ki)
2.4–3,836 (EC50)
16–98% (Emax)
5-HT2B 4.6–410 (Ki)
2.4–>20,000 (EC50)
38–84% (Emax)
5-HT2C 10–141 (Ki)
30.3 (EC50)
95.1% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 70–84
5-HT6 57–72
5-HT7 3.5–72
α1A–α1B >10,000
α2A 1,379–2,044
α2B 1,271–1,894
α2C 4,404
β1–β2 >10,000
D1 20–>14,000
D2 3,700–>10,000
D3 101–8,900
D4 >10,000
D5 >10,000
H1 1,600–>10,000
H2–H4 >10,000
M1–M5 >10,000
σ1 >10,000
σ2 >10,000
I2 792
TAAR1 1,400 (Ki) (rat)
17,000 (Ki) (mouse)
920–2,700 (EC50) (rodent)
>30,000 (EC50) (human)
SERTTooltip Serotonin transporter 3,800–>10,000 (Ki)
662–3,900 (IC50Tooltip half-maximal inhibitory concentration)
561 (EC50)
54% (Emax)
NETTooltip Norepinephrine transporter 13,000 (Ki)
14,000 (IC50)
>10,000 (EC50)
DATTooltip Dopamine transporter 6,000–>30,000 (Ki)
>100,000 (IC50)
>10,000 (EC50)
Notes: The smaller the value, the more avidly psilocin interacts with the site. Sources: [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]

4-PrO-DMT is theorized to be a serotonergic psychedelic, and is partial agonist of the 5-HT1D, 5-HT1B and 5-HT1A serotonin receptors.[1][23]

See also

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References

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  1. ^ a b c d e Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science. 6 (4): 567–577. doi:10.1021/acsptsci.2c00222. PMC 10111620. PMID 37082754.
  2. ^ European Monitoring Center for Drugs and Drug Addiction (December 2020). New psychoactive substances: global markets, glocal threats and the COVID-19 pandemic. An update from the EU Early Warning System (PDF). Luxembourg: Publications Office of the European Union. doi:10.2810/921262. ISBN 9789294975584. Archived (PDF) from the original on 2022-10-08. Retrieved 2021-06-17.
  3. ^ Raithatha SA, Hagel JM, Matinkhoo K, Yu L, Press D, Cook SG, et al. (November 2023). "Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders". Journal of Medicinal Chemistry. 67 (2): 1024–1043. doi:10.1021/acs.jmedchem.3c01225. PMC 10823477. PMID 37983270.
  4. ^ "Foundational Science for the Psilocybin Analog 4-PrO-DMT in Mice". CaaMTech. 28 March 2023. Archived from the original on 2024-03-03.
  5. ^ Liu T. "BindingDB BDBM50081701 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol::4-hydroxy-N,N-dimethyltryptamine::CHEMBL65547::N,N-dimethyl-4-hydroxytryptamine::Psilocin::US11427604, Compound (I-45)::US11453689, Compound Psilocin::US11591353, Compound I-45::US11597738, Example 3::US11642336, Compound Psilocin::US20240051978, Compound Psilocin". BindingDB. Retrieved 5 September 2024.
  6. ^ Liu T. "BindingDB BDBM50171269 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate::4-phosphoryloxy-N,N-dimethyltryptamine::CHEMBL194378::Indocybin::O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine::Psilocybine::US11597738, Example 4::psilocin phosphate ester::psilocybin". BindingDB. Retrieved 5 September 2024.
  7. ^ "PDSP Database". UNC (in Zulu). Retrieved 2024-09-05.
  8. ^ "PDSP Database". UNC (in Zulu). Retrieved 2024-09-05.
  9. ^ Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
  10. ^ Dodd S, Norman TR, Eyre HA, Stahl SM, Phillips A, Carvalho AF, Berk M (August 2023). "Psilocybin in neuropsychiatry: a review of its pharmacology, safety, and efficacy" (PDF). CNS Spectr. 28 (4): 416–426. doi:10.1017/S1092852922000888. PMID 35811423.
  11. ^ Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin - summary of knowledge and new perspectives". Eur Neuropsychopharmacol. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. PMID 24444771.
  12. ^ Wojtas A, Gołembiowska K (December 2023). "Molecular and Medical Aspects of Psychedelics". Int J Mol Sci. 25 (1): 241. doi:10.3390/ijms25010241. PMC 10778977. PMID 38203411.
  13. ^ Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). Eur Neuropsychopharmacol. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487.
  14. ^ Ray TS (February 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.
  15. ^ Plazas E, Faraone N (February 2023). "Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents". Biomedicines. 11 (2): 461. doi:10.3390/biomedicines11020461. PMC 9953455. PMID 36830997.
  16. ^ US 11440879, Andrew Carry Kruegel, "Methods of treating mood disorders", published 10 February 2022, assigned to Gilgamesh Pharmaceuticals, Inc. 
  17. ^ Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". The Journal of Pharmacology and Experimental Therapeutics. 341 (1): 251–262. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.
  18. ^ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
  19. ^ Wsół A (December 2023). "Cardiovascular safety of psychedelic medicine: current status and future directions". Pharmacol Rep. 75 (6): 1362–1380. doi:10.1007/s43440-023-00539-4. PMC 10661823. PMID 37874530.
  20. ^ Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem. 299 (10): 105231. doi:10.1016/j.jbc.2023.105231. PMC 10570959. PMID 37690691.
  21. ^ Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, Chang L, Gallant J, Press D, Bains JS, Raithatha S, Hagel J, Facchini P (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi:10.21203/rs.3.rs-2667175/v1, retrieved 18 March 2025
  22. ^ Gainetdinov RR, Hoener MC, Berry MD (July 2018). "Trace Amines and Their Receptors". Pharmacol Rev. 70 (3): 549–620. doi:10.1124/pr.117.015305. PMID 29941461.
  23. ^ Greene, Shaun L. (2022-01-01), Dargan, Paul; Wood, David (eds.), "Chapter18 - Tryptamines", Novel Psychoactive Substances (Second Edition), Boston: Academic Press, pp. 495–532, doi:10.1016/b978-0-12-818788-3.00014-0, ISBN 978-0-12-818788-3, retrieved 2024-08-29
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