2,5-Dimethoxy-4-propylamphetamine
Psychedelic drug
From Wikipedia, the free encyclopedia
2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM.[1][2] It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a propyl group.[1] The drug is taken orally.[1]
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| Other names | 2,5-Dimethoxy-4-propylamphetamine; 4-Propyl-2,5-dimethoxyamphetamine; DOPR; DOPr |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Onset of action | Very slow[1] |
| Duration of action | 20–30 hours[1] |
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| Formula | C14H23NO2 |
| Molar mass | 237.343 g·mol−1 |
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The drug acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[2][3] It produces psychedelic-like effects in animals.[2][3]
DOPR was first described in the literature by Alexander Shulgin in 1970.[4] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOPR's dose as 2.5 to 5 mg orally and its duration as 20 to 30 hours.[1] It is said to have a very slow onset.[1] The effects of DOPR have been reported to include closed-eye imagery, visuals, thinking changes, and insomnia and sleep disruption, among others.[1] In one of the reports, it was described as a "heavy duty psychedelic", including strong and unignorable visuals.[1]
Interactions
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.[2][5][6][3][7] It has very weak affinity for the serotonin 5-HT1 receptor.[8] The drug has also been assessed at other receptors.[2]
It produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents.[2][3] It is slightly more potent but slightly less efficacious than DOM in producing the head-twitch response.[2] 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.[2][3]
DOPR showed no significant effects on locomotor activity in rodents at the assessed doses, but showed a trend towards hyperlocomotion at the highest dose.[3] In a subsequent study however, it produced hyperlocomotion at lower doses and hypolocomotion at higher doses.[2] The drug has shown pro-motivational effects in rodents at sub-hallucinogenic doses or so-called "microdoses".[5][6][9] DOPR's close analogue DOET has also been clinically studied at sub-hallucinogenic doses as a "psychic energizer".[10][11][12][13][14][15] DOPR produces antidepressant-like effects in rodents.[9]
At higher doses, DOPR produces hypothermia in rodents.[2]
Pharmacokinetics
DOPR crosses the blood–brain barrier in rodents.[2] The drug showed the highest brain/plasma ratio among DOM homologues in rodents, whereas 2,5-dimethoxyamphetamine (2,5-DMA) showed the lowest.[2] This was involved in potency differences between the drugs.[2]
Chemistry
History
DOPR was first described in the literature by Alexander Shulgin in 1970.[4] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Legal status
Canada
DOPR is a controlled substance in Canada under phenethylamine blanket-ban language.[16]
United States
DOPR is not an explicitly controlled substance in the United States.[17] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.