2,5-Dimethoxy-4-propylamphetamine

2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[1] It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved).^[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR.

2,5-Dimethoxy-4-propylamphetamine

Clinical data
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; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	20–30 hours[1]
Identifiers
IUPAC name 1-(2,5-Dimethoxy-4-propylphenyl)propan-2-amine
CAS Number	63779-88-4 Y 53581-55-8 (hydrochloride)
PubChem CID	542051
ChemSpider	472021 Y
UNII	L3P287BI9W
ChEMBL	ChEMBL8569 Y
CompTox Dashboard (EPA)	DTXSID40337347
Chemical and physical data
Formula	C14H23NO2
Molar mass	237.343 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc(c(OC)cc1CC(N)C)CCC)C
InChI 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 Y
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Use and effects

According to Alexander Shulgin in PiHKAL, the dosage of DOPR is 2.5 to 5 mg and its duration is 20 to 30 hours.^[1] He described DOPR as a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion.^[1]

Pharmacology

Pharmacodynamics

DOPR acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.^[2][3][4][5]

It produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents.^[4] 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.^[4]

DOPR showed no significant effects on locomotor activity in rodents at the assessed doses, but showed a trend towards hyperlocomotion at the highest dose.^[4] The drug has shown pro-motivational effects in rodents at sub-hallucinogenic doses or so-called "microdoses".^[2][3] DOPR's close analogue 2,5-dimethoxy-4-ethylamphetamine (DOET) has also been clinically studied at sub-hallucinogenic doses as a "psychic energizer".^{[6][7][8][9][10][11]} The non-hallucinogenic analogue Ariadne has indirect dopaminergic effects in rodents^[4] and pro-motivational effects in monkeys as well.^[12]

Chemistry

Analogues

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]

Structure of DOIP.

See also

• ASR-2001
• DOPF
• DOx