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2,5-Dimethoxy-4-nitroamphetamine

2,5-Dimethoxy-4-nitroamphetamine
IUPAC name 1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine
Identifiers
CAS number
SMILES COc1cc(c(cc1CC(C)N)OC)N(=O)=O
Properties
Molecular formula C11H16N2O4
Molar mass 240.26 g/mol
Melting point

206-207 °C hydrochloride
231-232 °C (R)-Isomer
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

Contents

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 an active stereocenter and (R)-DON is the more active isomer. Concentrated solution is dark brown but transparent viscous liquid.

Effects

DON produces psychedelic and entheogenic effects that last up to 8-15 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 are tested on humans (usually in the mix with cannabis) to produce high-intensity psychedelic effect with colorful visuals. There was a report of long-lasting psychosis of the young man after taking 12.5 mg DON hydrochloride. Unlike DOB, DON shows visible stimulation effect, including muscular activity slightly similar to amphetamine. It also has been known to be less visual than most of its psychedelic amphetamine counterparts.

Pharmacology

The mechanism that produces the hallucinogenic and entheogenic effects of DON is unknown, but seems to be very close to DOB and analogs.

Dangers

The toxicity of DON is not known.

Legality

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. Regarding other factions in the world, possession of DON may be common in the practise of advanced psychiatry.

See also

External links

v • d • e
Psychedelic phenethylamines

Aleph • 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA-2 • DOB • DOC • DOET • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • Isoproscaline • Lophophine • MDA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Proscaline • TCB-2 • TMA
v • d • e
Drugs from PiHKAL

AEM · AL · Aleph · Aleph-2 · Aleph-4 · Aleph-6 · Aleph-7 · Ariadne · Asymbescaline · Buscaline · Beatrice · Bis-TOM · BOB · BOD · BOH · BOHD · BOM · 4-Bromo-3,5-dimethoxyamphetamine · 2-Bromo-4,5-methylenedioxyamphetamine · 2C-B · 3C-BZ · 2C-C · 2C-D · 2C-E · 3C-E · 2C-F · 2C-G · 2C-G-3 · 2C-G-4 · 2C-G-5 · 2C-G-N · 2C-H · 2C-I · 2C-N · 2C-O · 2C-O-4 · 2C-P · CPM · 2C-SE · 2C-T · 2C-T-2 · 2C-T-4 · psi-2C-T-4 · 2C-T-7 · 2C-T-8 · 2C-T-9 · 2C-T-13 · 2C-T-15 · 2C-T-17 · 2C-T-21 · 4-D · beta-D · DESOXY · 2,4-DMA · 2,5-DMA · 3,4-DMA · DMCPA · DME · DMMDA · DMMDA-2 · DMPEA · DOAM · DOB · DOBU · DOC · DOEF · DOET · DOI · DOM · psi-DOM · DON · DOPR · Escaline · EEE · EEM · EME · EMM · Ethyl-J (EBDB) · Ethyl-K · F-2 · F-22 · Flea · 3C-G-3 · 3C-G-4 · 3C-G-5 · 3C-G-N · Ganesha · HOT-2 · HOT-7 · HOT-17 · IDNNA · Isomescaline · Isoproscaline · Iris · J (BDB) · Lophophine · Mescaline · 4-MA · Madam-6 · Methallylescaline · MDA · MDAL · MDBU · MDBZ · MDCPM · MDDM · MDE · MDHOET · MDIP · MDMA · MDMC (EDMA) · MDMEO · MDMEOET · MDMP · MDOH · MDPEA · MDPH · MDPL · MDPR · Metaescaline · MEDA · MEE · MEM · MEPEA · Meta-DOB · Meta-DOT · Methyl-DMA · Methyl-DOB · Methyl-J (MBDB) · Methyl-K · Methyl-MA (PMMA) · Methyl-MMDA-2 · MMDA · MMDA-2 · MMDA-3a · MMDA-3b · MME · Metaproscaline · MPM · Ortho-DOT · Proscaline · Phenescaline · Phenethylamine · Propynyl · Symbescaline · 2,3,4,5-Tetramethoxyamphetamine · 3-TASB · 4-TASB · 5-TASB · Thiobuscaline · 3-TE · 4-TE · 3-TIM · 4-TIM · 5-TIM · 3-TM · 4-TM · TMA · TMA-2 · TMA-3 · TMA-4 · TMA-5 · TMA-6 · 3-TME · 4-TME · 5-TME · 2T-MMDA-3a · 4T-MMDA-2 · 2-TOET · 5-TOET · 2-TOM · 5-TOM · TOMSO · Thioproscaline · Trisescaline · 3-TSB · 4-TSB · 3-T-Trisescaline · 4-T-Trisescaline
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