CAS number 67460-68-8
ChemSpider 95083 YesY
Jmol-3D images Image 1
Image 2
Molecular formula C11H16N2O4
Molar mass 240.26 g/mol
Melting point

206-207 °C hydrochloride
231-232 °C (R)-Isomer

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,5-Dimethoxy-4-nitroamphetamine (DON) is an analogue of DOM and DOB. It is also closely related to 2C-N, and produces hallucinogenic, psychedelic, and entheogenic effects.



DON is in a class of compounds commonly known as alpha-methyl phenethylamines, or amphetamines and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has an active stereocenter and (R)-DON is the more active isomer. Concentrated solution is dark brown but transparent viscous liquid.


DON produces psychedelic and entheogenic effects that last up to 8–30 hours. In his book PiHKAL (Phenethylamines i Have Known And Loved), Alexander Shulgin lists a dosage of DON as being 3-4.5 mg orally. When dropped into nose, the dose is the same but onset is shorter. Dosages up to 7.5 mg reportedly produce high-intensity psychedelic effect with colorful visuals. There was a report of long-lasting psychosis in a young man after taking 12.5 mg DON hydrochloride.[citation needed] Unlike DOB, DON shows visible stimulation effect, including muscular activity slightly similar to amphetamine. It also has been known to be more visual than most of its psychedelic amphetamine counterparts.


The mechanism that produces the hallucinogenic and entheogenic effects of DON is similar to that of DOB and other analogs, this being agonist activity at a number of serotonin receptors, primarily 5-HT2A, 5-HT2C and 5-HT1A.


The toxicity of DON is not known.


DON is unscheduled and unregulated in the United States, however 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. DON is Class A in the UK after the table of contents of Pihkal and Tihkal were added to the schedules.

See also

  • 2,5-Dimethoxy-4-Substituted Amphetamines

External links

Wikimedia Foundation. 2010.

Look at other dictionaries:

  • DOx — 2,5 Dimethoxyamphetamine (2,5 DMA), the base structure of the DOx family. DOx is a term used to refer to a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2 and 5 positions of the phenyl ring, and a… …   Wikipedia

  • Substituted amphetamine — Optical isomers of amphetamine D amphetamine …   Wikipedia

  • Don — or DON may refer to Contents 1 People 2 Chemistry 3 Geography 4 …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.