2,5-Dimethoxy-4-propylamphetamine


2,5-Dimethoxy-4-propylamphetamine is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. 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. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL.

Use and effects

In his book PiHKAL, 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.

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. It has very weak affinity for the serotonin 5-HT1 receptor. The drug has also been assessed at other receptors.
It produces the head-twitch response, 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". DOPR produces antidepressant-like effects in rodents.
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 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. Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL.

Society and culture

Legal status

Canada

DOPR is a controlled substance in Canada under phenethylamine blanket-ban language.

United States

DOPR is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.