4-PrO-DMT

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]

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

Recreational use

4-PrO-DMT Crystals.

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.^[1][4]

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.^[1]

Interactions

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

Pharmacology

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-HT_1D, 5-HT_1B and 5-HT_1A serotonin receptors.^[1][23]

See also

• 4-HO-DMT
• 4-AcO-DMT
• 5-MeO-DMT
• CT-4201
• FT-104
• Psilocybin