4-PrO-DMT

{{drugbox

| drug_name = 4-PrO-DMT

| image = 4-PrO-DMT.svg

| image2 = 4-PrO-DMT 3D BS.png

| legal_UK =

| legal_DE =

| C = 15 | H = 20 | N = 2 | O = 2

| IUPAC_name = [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] propanoate

| CAS_number = 1373882-11-1

| ChemSpiderID = 84400449

| PubChem = 155907598

| UNII = B9BF25HPH4

| synonyms = 4-Propanoyloxy dmt

| smiles = CCC(=O)OC1=CC=CC2=C1C(=CN2)CCN(C)C

| StdInChI = 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

| StdInChIKey = 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.{{cite journal | vauthors = Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH | title = Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 4 | pages = 567–577 | date = April 2023 | pmid = 37082754 | pmc = 10111620 | doi = 10.1021/acsptsci.2c00222 }} It produces a head-twitch response in mice. 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.{{cite book | url = https://www.emcdda.europa.eu/system/files/publications/13464/20205648_TD0320796ENN_PDF_rev.pdf | title = New psychoactive substances: global markets, glocal threats and the COVID-19 pandemic. An update from the EU Early Warning System | author = European Monitoring Center for Drugs and Drug Addiction | location = Luxembourg | publisher = Publications Office of the European Union | date = December 2020 | doi = 10.2810/921262 | isbn = 9789294975584 | access-date = 2021-06-17 | archive-date = 2022-10-08 | archive-url = https://web.archive.org/web/20221008161408/http://www.emcdda.europa.eu/system/files/publications/13464/20205648_TD0320796ENN_PDF_rev.pdf | url-status = live }} A number of related derivatives have been synthesized as prodrugs of psilocin for medical applications.{{cite journal | vauthors = Raithatha SA, Hagel JM, Matinkhoo K, Yu L, Press D, Cook SG, Sharma G, Dhananjaya D, Jensen G, Lee JB, Cai C, Gallant J, Bains J, Tucker JE, Facchini PJ | display-authors = 6 | title = Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders | journal = Journal of Medicinal Chemistry | volume = 67| issue = 2| date = November 2023 | pages = 1024–1043 | pmid = 37983270 | doi = 10.1021/acs.jmedchem.3c01225 | doi-access = free | pmc = 10823477 }}

Recreational use

File:4-Propionoxy-N,N-dimethyltryptamine.jpg

= Dosage =

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.{{Cite web |title=Foundational Science for the Psilocybin Analog 4-PrO-DMT in Mice |url=https://caam.tech/foundational-science-for-the-psilocybin-analog-4-pro-dmt-in-mice/ |url-status=live |website=CaaMTech |date=28 March 2023 |archive-url=https://web.archive.org/web/20240303000330/https://caam.tech/foundational-science-for-the-psilocybin-analog-4-pro-dmt-in-mice/|archive-date=2024-03-03 }}

Interactions

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

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.{{Citation |last=Greene |first=Shaun L. |title=Chapter18 - Tryptamines |date=2022-01-01 |work=Novel Psychoactive Substances (Second Edition) |pages=495–532 |editor-last=Dargan |editor-first=Paul |url=https://linkinghub.elsevier.com/retrieve/pii/B9780128187883000140 |access-date=2024-08-29 |place=Boston |publisher=Academic Press |doi=10.1016/b978-0-12-818788-3.00014-0 |isbn=978-0-12-818788-3 |editor2-last=Wood |editor2-first=David}}

= 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.