2,5-Dimethoxy-4-nitroamphetamine

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug and amphetamine. It is an analog of DOM and DOB. It is also closely related to 2C-N.

2,5-Dimethoxy-4-nitroamphetamine

Names
Preferred IUPAC name 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine
Identifiers
CAS Number	67460-68-8 Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL8301 Y
ChemSpider	95083 Y
PubChem CID	105432
UNII	3FIV60666J Y
CompTox Dashboard (EPA)	DTXSID00874243
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 InChI=1/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 Key: JQJRESSXOVAECC-UHFFFAOYAW
SMILES COc1cc(c(cc1CC(C)N)OC)N(=O)=O [O-][N+](=O)c1cc(OC)c(cc1OC)CC(N)C
Properties
Chemical formula	C11H16N2O4
Molar mass	240.259 g·mol−1
Melting point	206 to 207 °C (403 to 405 °F; 479 to 480 K) (hydrochloride) 231-232 °C ((R)-isomer)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemistry

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 a stereocenter.

Effects

In his book PiHKAL, Alexander Shulgin lists a dosage of DON as being 3-4.5 mg orally with amphetamine-like stimulation lasting 8–15 hours.

Dangers

The toxicity of DON is not known.

Legality

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. 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