2,5-Dimethoxy-4-nitroamphetamine

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug and amphetamine.^[1] It is an analogue of DOM and DOB.^[1] It is also closely related to 2C-N.^[1] The drug is a serotonin 5-HT₂ receptor agonist.^[2]

DON

Clinical data
Other names	DON; 2,5-Dimethoxy-4-nitroamphetamine; 4-Nitro-2,5-dimethoxyamphetamine
Routes of administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine
CAS Number	67460-68-8 Y
PubChem CID	105432
ChemSpider	95083 Y
UNII	3FIV60666J
ChEMBL	ChEMBL8301 Y
CompTox Dashboard (EPA)	DTXSID00874243
Chemical and physical data
Formula	C11H16N2O4
Molar mass	240.259 g·mol−1
3D model (JSmol)	Interactive image
Melting point	206 to 207 °C (403 to 405 °F) (hydrochloride) 231-232 °C ((R)-isomer)[1]
SMILES COc1cc(c(cc1CC(C)N)OC)N(=O)=O
InChI InChI=1S/C11H16N2O4/c1-7(12)4-8-5-11(17-3)9(13(14)15)6-10(8)16-2/h5-7H,4,12H2,1-3H3 Y Key:JQJRESSXOVAECC-UHFFFAOYSA-N Y
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Use and effects

In his book PiHKAL, Alexander Shulgin lists a dosage of DON as being 3 to 4.5 mg orally with amphetamine-like stimulation and mild psychedelic effects lasting 8 to 15 hours.^[1]

Pharmacology

DON acts as a serotonin 5-HT_2A and 5-HT_2C receptor partial agonist, albeit with far lower potency and efficacy than other DOx drugs.^[2] It is also a serotonin 5-HT_2B receptor partial agonist.^[3] Earlier studies have also reported its affinities at serotonin receptors, including the serotonin 5-HT₂ and 5-HT₁ receptors.^[4][5] The drug produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.^[6]

Chemistry

DON is in a class of compounds commonly known as α-methyl phenethylamines, or amphetamines and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has a stereocenter.

Society and culture

Legal status

DON is unscheduled in the United States, but because of its close similarity in structure and effects to DOM and DOB, possession and sale of DON may be subject to prosecution under the Federal Analog Act.^{[citation needed]} DON is listed as a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act after the table of contents of PiHKAL and TiHKAL were added to the schedules.

See also

• DOx