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;
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. 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]

Recreational use

4-PrO-DMT Crystals

Dosage

4-PrO-DMT is reported to be orally active, though its threshold and duration in humans have not been formally studied.[3]

Effects

The effects of 4-PrO-DMT are broadly comparable to those of other serotonergic psychedelics such as LSD and psilocybin.[4]

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.[5]

Similar to 4-AcO-DMT, 4-PrO-DMT is believed to be a pro-drug of psilocin, as well as showing some direct serotonin receptor agonist effects in its own right.[6]

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

Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (March 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N, N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science. doi:10.1021/acsptsci.2c00222.}
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.
Rossouw F (2018-12-06). "Why are Psilocin and Psilocybin Orally Active?". Medium. Retrieved 2023-01-05.
Andersen KA, Carhart-Harris R, Nutt DJ, Erritzoe D (February 2021). "Therapeutic effects of classic serotonergic psychedelics: A systematic review of modern-era clinical studies". Acta Psychiatrica Scandinavica. 143 (2): 101–118. doi:10.1111/acps.13249. PMID 33125716. S2CID 226217912.
Celada P, Bortolozzi A, Artigas F (September 2013). "Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research". CNS Drugs. 27 (9): 703–716. doi:10.1007/s40263-013-0071-0. PMID 23757185. S2CID 31931009.
Mashkovsky MD, Yakhontov LN (1969). "Relationships between the chemical structure and pharmacological activity in a series of synthetic quinuclidine derivatives". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques. 13: 293–339. doi:10.1007/978-3-0348-7068-9_6. ISBN 978-3-0348-7070-2. PMID 4391190.

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[1] Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (March 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N, N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science. doi:10.1021/acsptsci.2c00222.}

[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.

[3] Rossouw F (2018-12-06). "Why are Psilocin and Psilocybin Orally Active?". Medium. Retrieved 2023-01-05.

[4] Andersen KA, Carhart-Harris R, Nutt DJ, Erritzoe D (February 2021). "Therapeutic effects of classic serotonergic psychedelics: A systematic review of modern-era clinical studies". Acta Psychiatrica Scandinavica. 143 (2): 101–118. doi:10.1111/acps.13249. PMID 33125716. S2CID 226217912.

[5] Celada P, Bortolozzi A, Artigas F (September 2013). "Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research". CNS Drugs. 27 (9): 703–716. doi:10.1007/s40263-013-0071-0. PMID 23757185. S2CID 31931009.

[6] Mashkovsky MD, Yakhontov LN (1969). "Relationships between the chemical structure and pharmacological activity in a series of synthetic quinuclidine derivatives". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques. 13: 293–339. doi:10.1007/978-3-0348-7068-9_6. ISBN 978-3-0348-7070-2. PMID 4391190.