2,5-Dimethoxy-4-propylamphetamine

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DOPR
Clinical data
Other names2,5-Dimethoxy-4-propylamphetamine; 4-Propyl-2,5-dimethoxyamphetamine; DOPR; DOPr
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of actionVery slow[1]
Duration of action20–30 hours[1]
Identifiers
  • 1-(2,5-dimethoxy-4-propylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC14H23NO2
Molar mass237.343 g·mol−1
3D model (JSmol)
  • O(c1cc(c(OC)cc1CC(N)C)CCC)C
  • InChI=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 ☒N
  • Key:UEEAUFJYLUJWQJ-UHFFFAOYSA-N checkY
  (verify)

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]

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

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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

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

Pharmacology

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Pharmacodynamics

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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] DOPR's close analogue DOET has also been clinically studied at sub-hallucinogenic doses as a "psychic energizer".[9][10][11][12][13][14]

At higher doses, DOPR produces hypothermia in rodents.[2]

Pharmacokinetics

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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

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Synthesis

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The chemical synthesis of DOPR has been described.[1]

Analogues

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The alternative structural isomer DOIP, with a 4-isopropyl substitution, is also known but is around ten times weaker than DOPR, with an active dose of some 20–30 mg (as compared to 2–5 mg for DOPR).[1]

History

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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]

See also

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References

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