4-PrO-DMT

4-PrO-DMT
Clinical data
Other names	4-Propanoyloxy dmt
Identifiers
	IUPAC name [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] propanoate;
CAS Number	1373882-11-1;
PubChem CID	155907598;
ChemSpider	84400449;
UNII	B9BF25HPH4;
CompTox Dashboard (EPA)	DTXSID501336912 ;
Chemical and physical data
Formula	C15H20N2O2
Molar mass	260.337 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)OC1=CC=CC2=C1C(=CN2)CCN(C)C;
	InChI 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 synthesised as prodrugs of psilocin for medical applications.^[3]

Recreational use

Dosage

4-PrO-DMT is reported to be orally active, though its threshold and duration in humans have not been formally studied.

Effects

The effects of 4-PrO-DMT are similar to those of psilocin (4-HO-DMT), as it acts as a prodrug.

Pharmacology

Pharmacodynamics

4-PrO-DMT is theorized to be a serotonergic psychedelic, and is partial agonist of the 5-HT_1D, 5-HT_1B and 5-HT_1A serotonin receptors.

Toxicity

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.

References

^ ^a ^b 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.
^ 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.
^ 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.

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[Glatfelter_2023-1] 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.

[pmid37983270-3] 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.

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