DON was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973. Its properties and effects in humans were described by Juan Sebastian Gomez-Jeria and colleagues in the mid-1980s. Subsequently, the drug was reviewed by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). DON was encountered as a novel designer drug in Japan by the late 2000s.
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DON's dose as 3.0 to 4.5mg orally and its duration as 8 to 15hours. The 3mg dose produced mostly stimulant-like effects while the 4.5mg dose produced full hallucinogenic effects. Its onset was a little over 1hour. The duration of the psychedelic effects was about 8hours and the duration of the stimulation was at least 14hours, although in some people the psychedelic effects were longer-lasting.
The drug's effects were reported to include enhanced color perception, intense visual hallucinations, some auditory distortion, strong amphetamine-like stimulation, a frequent desire for physical activity, anxiety, stomach cramps, slight hypothermia, and little or no physical malaise. It was said to have very similar qualitative effects to those of DOB except for its additional strong stimulant component. Due to its pronounced stimulant effects, it was hypothesized that DON might have a reduced likelihood of potentially unpleasant and insightful experiences and thus might have more recreational potential.
DON is in a class of compounds commonly known as α-methylphenethylamines, or amphetamines and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has a stereocenter.
DON was first described in the scientific literature by Ronald Coutts and Jerry Malicky by 1973. Its properties and effects in humans were described by Juan Sebastian Gomez-Jeria and colleagues in 1986 and 1987. Subsequently, the drug was reviewed by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). DON was encountered as a novel designer drug in Japan by 2008 or 2009.
1234567891011Gómez-Jeria, JS; Cassels, BK; Clavijo, R; Vargas, V; Quintana, R; Saavedra-Aguilar, JC. (1986). Spectroscopic characterization of a new hallucinogen: 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON). Microgram 19 (11), 153–161. https://isomerdesign.com/bitnest/external/Microgram/19.11 "Here we can say that a dose of 4.5 mg of DON nitrate produces the standard effects described in the literature (10,11). The only qualitative difference between DON and its 4-Br analog (008) is that DON has a very strong stimulating action reminiscent of amphetamine. This action seems to reduce the incidence of insightful, and therefore potentially unpleasant experiences, and thus seems likely to appear on the market as an illicit recreational drug."
123456789101112131415Gomez-Jeria JS, Cassels BK, Saavedra-Aguilar JC (1987). "A quantum-chemical and experimental study of the hallucinogen (±)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)". European Journal of Medicinal Chemistry. 22 (5): 433–437. doi:10.1016/0223-5234(87)90032-8. (±)-DON nitrate was subjected to preliminary screening by eight normal volunteers familiar with the effects of psychotropic substances, following published procedure [17]. Once the active dose level had been established, the number of subjects was increased to a total of 16 (12 male, 4 female, aged 21—51 years), with a total of 30 trials. [...] The subjects were asked to describe their experiences at the end of each session. [...] DON may be a potent hallucinogen, if its relatively poor lipid solubility does not prevent it from reaching the CNS efficiently. Acute oral administration of a total dose of 2 mg of the racemic nitrate (6.6 μmol) results, after a period of a little more than 1 h, in an amphetamine-like stimulated state. When 3 mg (10 μmol) are taken, these symptoms are maintained but stomach cramps and anxiety appear, the volunteers declaring that the general feeling is suggestive of the beginning of a hallucinogenic experience. At a total dose of 4.5 mg (15 μmol), the malaise is minimal or absent, and a psychedelic (not psychotomimetic) state ensues, with intense visual hallucinations, enhanced perception of color, slight hyperthermia and often a desire for physical activity. Visual and sometimes auditive distortions persist for about 8 h and amphetamine-like stimulation is usually present at least into the 14th h, although some subjects also reported longer-lasting psychedelic experiences.
12Uchiyama N, Miyazawa N, Kawamura M, Kikura-Hanajiri R, Goda Y (February 2010). "[Analysis of newly distributed designer drugs detected in the products purchased in fiscal year 2008]". Yakugaku Zasshi (in Japanese). 130 (2): 263–270. doi:10.1248/yakushi.130.263. PMID20118651.
↑Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". Journal of Medicinal Chemistry. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
↑Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". European Journal of Pharmacology. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID6479216.
