2,5-Dimethoxy-4-propylamphetamine

Psychedelic drug verified verified 477211774 DOPR DOPR chemical structure.svg skin-invert-image 250px DOPR-3d-sticks.png bg-transparent 225px Oral Serotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen None Schedule I NpSG Class A Very slow 20–30 hours correct CAS 63779-88-4 53581-55-8 (hydrochloride) correct FDA L3P287BI9W 542051 correct drugbank correct chemspider 472021 correct EBI 8569 2,5-Dimethoxy-4-propylamphetamine; 4-Propyl-2,5-dimethoxyamphetamine; DOPR; DOPr 1-(2,5-dimethoxy-4-propylphenyl)propan-2-amine 14 23 1 2 CCCC1=CC(=C(C=C1OC)CC(C)N)OC changed chemspider 1S/C15H25NO2/c1-5-6-11-8-14(17-4)12(7-10(2)15)9-13(11)16-3/h8-10H,5-7,15H2,1-4H3 correct chemspider UEEAUFJYLUJWQJ-UHFFFAOYSA-N 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. PiHKAL: A Chemical Love Story Shulgin A, Shulgin A Transform Press United States 0-9630096-0-5 978 http://www.erowid.org/library/books_online/pihkal/pihkal.shtml September 1991 Luethi D, Glatfelter GC, Pottie E, Sellitti F, Maitland AD, Gonzalez NR, Kryszak LA, Jackson SN, Hoener MC, Stove CP, Liechti ME, Smieško M, Baumann MH, Simmler LD, Rudin D The 4-alkyl chain length of 2,5-dimethoxyamphetamines differentially affects in vitro serotonin receptor actions versus in vivo psychedelic-like effects Mol Psychiatry November 2025 41193673 10.1038/s41380-025-03325-1 https://www.nature.com/articles/s41380-025-03325-1.pdf It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a propyl group. The drug is taken orally. The drug acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. It produces psychedelic-like effects in animals. DOPR was first described in the literature by Alexander Shulgin in 1970.phenethylamines and their pharmacologically-acceptable salts Google Patents 14 July 1969 https://patents.google.com/patent/US3547999 27 November 2025 Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOPR's dose as 2.5 to 5mg orally and its duration as 20 to 30hours. It is said to have a very slow onset. The effects of DOPR have been reported to include closed-eye imagery, visuals, thinking changes, and insomnia and sleep disruption, among others. In one of the reports, it was described as a "heavy duty psychedelic", including strong and unignorable visuals. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics DOPR acts as an agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. Noback M, Kenton JA, Klein AK, Hughes ZA, Kruegel AC, Schmid Y, Halberstadt AL, Young JW Low (micro)doses of 2,5-dimethoxy-4-propylamphetamine (DOPR) increase effortful motivation in low-performing mice Neuropharmacology 268 110334 February 2025 39900138 10.1016/j.neuropharm.2025.110334 According to a recent publication (Cunningham et al., 2023), DOPR acts as a potent agonist at the 5-HT2A receptor when tested in BRET assays of Gq dissociation (EC50 = 1.7 nM, Emax = 98.9% relative to 5-HT) and β-arrestin2 recruitment (EC50 = 7.96 nM, Emax = 99.8% relative to 5-HT). free Noback M, Kenton J, Klein A, Hughes Z, Kruegel A, Young J ACNP 61st Annual Meeting: Poster Abstracts P541 - P809: P572. 2,5-Dimethoxy-4-Propylamphetamine (DOPR) Increased Effortful Motivation in Mice Neuropsychopharmacology 47 Suppl 1 371–520 (390–390) December 2022 36456695 9714408 10.1038/s41386-022-01486-z DOPR caused a dose-dependent increase in HTR (F(5,30)=60.0, p < 0.0001), with doses of 3.2 and 10 mg/kg passing a Bonferroni post hoc correction relative to vehicle (p < 0.002), and peak effect at 3.2 mg/kg. [...] The binding affinity at 5-HT2A of the two compounds was similar, with DOPR having a Ki of 17.56 nM and DOI having a Ki of 14.51 nM. [...] DOPR and DOI also show agonist activity at 5-HT2A (EC50 of 0.12 and 0.19 nM, respectively) and 5-HT2C (EC50 of 0.27 and 0.82 nM, respectively) receptors, with >25-fold lower potency at 5-HT2B receptors and no significant activity at 5-HT1A (both > 1,000 nM EC50). [...] The positive effect of DOPR on effortful motivation points to possible therapeutic applications in psychiatric illness states characterized by reduced effortful motivation as measured by the PRBT. The similarity of effects of DOPR to well-studied drugs such as DOI and amphetamine provides a useful reference point to interpret its pharmacological effects. Importantly, the doses needed to increase breakpoint in the PRBT were as low as 0.0106 mg/kg. While 0.1 mg/kg increased HTR, this effect was not significant, and maximal effect at 3.2 mg/kg, supporting the premise that low doses of DOPR may be therapeutic in anhedonia states without causing unwanted hallucinogenic side effects. Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D January 2023 Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs ACS Chemical Neuroscience 14 1 119–135 10.1021/acschemneuro.2c00597 10147382 36521179 We propose the following rationale for the rapid effects of Ariadne in the mouse [Parkinson's disease (PD)] model, as an initial guiding hypothesis for future studies. The in vitro profile suggests that Ariadne’s effect on dopamine neurotransmission is indirect, namely not via direct modulation of DAT or dopamine receptors. It has been demonstrated that 5-HT2A agonists increase dopamine release in nucleus accumbens and other regions of the mesolimbic system.43 It is therefore likely that 5-HT2A agonists also stimulate DA release in more dorsal areas of the striatum that are compromised by the PD pathology. Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors Frontiers in Pharmacology 14 1101290 2023 36762110 9902381 10.3389/fphar.2023.1101290 free It has very weak affinity for the serotonin 5-HT1 receptor. Glennon RA Central serotonin receptors as targets for drug research J Med Chem 30 1 1–12 January 1987 3543362 10.1021/jm00384a001 Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites The drug has also been assessed at other receptors. It produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents. It is slightly more potent but slightly less efficacious than DOM in producing the head-twitch response. As with many other psychedelics, DOPR shows an inverted U-shaped dose–response curve in terms of the HTR, increasing it at lower doses and having diminished effectiveness at higher doses. DOPR showed no significant effects on locomotor activity in rodents at the assessed doses, but showed a trend towards hyperlocomotion at the highest dose. In a subsequent study however, it produced hyperlocomotion at lower doses and hypolocomotion at higher doses. The drug has shown pro-motivational effects in rodents at sub-hallucinogenic doses or so-called "microdoses". DOPR's close analogue DOET has also been clinically studied at sub-hallucinogenic doses as a "psychic energizer". Baggott MJ Learning about STP: A Forgotten Psychedelic from the Summer of Love History of Pharmacy and Pharmaceuticals 65 1 1 October 2023 2694-3034 10.3368/hopp.65.1.93 free 93–116 https://hopp.uwpress.org/content/wphopp/65/1/93.full.pdf 26 January 2025 Iversen LL, Iversen SD, Snyder SH Shulgin AT Stimulants Psychotomimetic Drugs: Structure-Activity Relationships Springer US Boston, MA 1978 978-1-4757-0512-6 10.1007/978-1-4757-0510-2_6 243–333 https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 Snyder SH, Faillace LA, Weingartner H DOM (STP), a new hallucinogenic drug, and DOET: effects in normal subjects Am J Psychiatry 125 3 113–120 September 1968 4385937 10.1176/ajp.125.3.357 Snyder SH, Faillace LA, Weingartner H A new psychotropic agent. Psychological and physiological effects of 2,5-dimethoxy-4-ethyl amphetamine (DOET) in man Arch Gen Psychiatry 21 1 95–101 July 1969 4389442 10.1001/archpsyc.1969.01740190097014 Snyder SH, Weingartner H, Faillace LA DOET (2,5-dimethoxy-4-ethylamphetamine), a new psychotropic drug. Effects of varying doses in man Arch Gen Psychiatry 24 1 50–55 January 1971 4923215 10.1001/archpsyc.1971.01750070052006 Snyder SH, Unger S, Blatchley R, Barfknecht CF Stereospecific actions of DOET (2,5-dimethoxy-4-ethylamphetamine) in man Arch Gen Psychiatry 31 1 103–106 July 1974 4599412 10.1001/archpsyc.1974.01760130079013 DOPR produces antidepressant-like effects in rodents.Noback M, Flesher M, Cuccurazzu B, Halberstadt A, Young J ACNP 64th Annual Meeting: Poster Abstracts P584-P872: The psychedelic DOPR improves depression-related behavior in mice Neuropsychopharmacology 51 S1 2026 0893-133X 41507446 12783840 10.1038/s41386-025-02281-2 410–571 https://www.nature.com/articles/s41386-025-02281-2 18 January 2026 At higher doses, DOPR produces hypothermia in rodents. Pharmacokinetics DOPR crosses the blood–brain barrier in rodents. The drug showed the highest brain/plasma ratio among DOM homologues in rodents, whereas 2,5-dimethoxyamphetamine (2,5-DMA) showed the lowest. This was involved in potency differences between the drugs. Chemistry Synthesis The chemical synthesis of DOPR has been described. Analogues Analogues of DOPR include DOM, DOET, DOiP, DOBU, DOAM, DOPF, 2C-P, and 4C-P, among others. History DOPR was first described in the literature by Alexander Shulgin in 1970.phenethylamines and their pharmacologically-acceptable salts Google Patents 14 July 1969 https://patents.google.com/patent/US3547999 27 November 2025 Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Society and culture Legal status Canada DOPR is a controlled substance in Canada under phenethylamine blanket-ban language.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 United States DOPR is not an explicitly controlled substance in the United States. Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) January 2026 U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division United States https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption. See also DOx (psychedelics) Stimulant § Serotonin 5-HT2A receptor agonists Motivation-enhancing drug § Serotonin 5-HT2A receptor agonists ASR-2001 DOPF Ariadne References External links DOPR - Isomer Design DOPR - PiHKAL - Erowid DOPR - PiHKAL - Isomer Design DOPR - The Shulgin Index DOPR - TripSit The Small & Handy DOPR Thread - Bluelight DOPR: Why It’s Wise to Avoid This Shulgin Psychedelic - Tripsitter Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Designer drugs Category:DOx (psychedelics) Category:PiHKAL Category:Pro-motivational agents Category:Psychedelic phenethylamines