View source for 2,5-Dimethoxy-4-nitroamphetamine

'''DON'''
2,5-DIMETHOXY-4-NITROAMPHETAMINE



== SYNTHESIS ==
A solution of 8.4 g 2,5-dimethoxyamphetamine base in 40 mL acetic acid was added dropwise over the course of 0.5 h to 43 mL of 50% nitric acid which was well stirred and cooled with an external ice bath. The resulting solution was quenched with ice water, made basic with aqueous NaOH, and extracted with a benzene-ether mixture. The residue that remained after the removal of the solvent was dissolved in dilute HCl which, upon evaporation of the H2O, yielded a nearly colorless residue. Recrystallization from an ethanol/ether mixture gave, after drying, 10.5 g of 2,5-dimethoxy-4-nitroamphetamine hydrochloride (DON) with a mp of 206-207 °C. The acetamide derivative melted at 166-168 °C. The formamide derivative was easily hydrolyzed with 3N HCl. And the R-isomer of DON hydrochloride had a mp of 231-232 °C.
{{chembox
| ImageFile = Dimethoxynitroamphetamine.png
| ImageSize = 200px
| IUPACName = 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine
| OtherNames = 
| Section1 = {{Chembox Identifiers
| CASNo = 67460-68-8
| PubChem = 
| SMILES = COc1cc(c(cc1CC(C)N)OC)N(=O)=O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>11</sub>H<sub>16</sub>N<sub>2</sub>O<sub>4</sub>
| MolarMass = 240.26 g/mol
| Appearance = 
| Density = 
| MeltingPt = 206-207 °C [[hydrochloride]]<br>231-232 °C (''R'')-[[Isomer]]
| BoilingPt = 
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards = 
| FlashPt = 
| Autoignition = }}
}}
== DOSAGE ==
3.0 - 4.5 mg.


== DURATION ==
8 - 15 h.


== QUALITATIVE COMMENTS ==
(with 3.0 mg) There was an amphetamine-like stimulation that was apparent an hour into it, and considerable anxiety. I had stomach cramps, but there were indications that there might be something hallucinogenic at a higher dose.

(with 4.5 mg) An enhancement of color perception, and some auditory distortion, that was still noticeable some eight hours into the experience. The visual changes were intense. I felt I was running a slight fever, and was restless, but there was almost no physical malaise. I was still somewhat wound up even at the 14th hour.


== EXTENSIONS AND COMMENTARY ==
These qualitative comments are not true quotations, but have been reconstructed from the published summaries of the human trials reported by several South American researchers. I have personally never tasted DON and have only these fragments from which to create a portrait of activity. A brief quotation, from a note published by these researchers in a bulletin that is restricted to forensic scientists serving law enforcement agencies, is certainly subject to a number of interpretations. It reads as follows: "This action [a strong stimulant action reminiscent of amphetamine] seems to reduce the incidence of insightful, and therefore potentially unpleasant experiences, and thus [DON seems likely] to appear on the market as an illicit recreational drug." I must admit that I have tried, and I am still not able, to interpret this quotation. 
[[Category:Drugs]]
[[Category:PiHKAL]]
[[Category:Shulgin]]

{{PiHKAL}}