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2,5-Dimethoxy-4-nitroamphetamine

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2,5-Dimethoxy-4-nitroamphetamine

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2,5-Dimethoxy-4-nitroamphetamine
IUPAC name

1-(2,5-Dimethoxy-4-nitrophenyl)propan-2-amine
Identifiers
CAS number 67460-68-8
ChemSpider 95083 YesY
ChEMBL CHEMBL8301 YesY
Jmol-3D images Image 1
Image 2
Properties
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.

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 8–30 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.

Pharmacology

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.

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. DON is Class A in the UK after the table of contents of Pihkal and Tihkal were added to the schedules.

See also

External links
Psychedelics
5-HT2AR agonists
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
Miscellaneous
Others
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 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 • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous

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