2,5-Dimethoxy-4-nitroamphetamine

Last updated
DON
DON2DACS.svg
Clinical data
Other namesDON; 2,5-Dimethoxy-4-nitroamphetamine; 4-Nitro-2,5-dimethoxyamphetamine
Routes of
administration 		Oral
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H16N2O4
Molar mass 240.259 g·mol−1
3D model (JSmol)
Melting point 206 to 207 °C (403 to 405 °F) (hydrochloride)
231-232 °C ((R)-isomer) [1]
  • COc1cc(c(cc1CC(C)N)OC)N(=O)=O
  • 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 Yes check.svgY
  • Key:JQJRESSXOVAECC-UHFFFAOYSA-N Yes check.svgY
   (verify)

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug and amphetamine. [1] It is an analogue of DOM and DOB. [1] It is also closely related to 2C-N. [1] The drug is a serotonin 5-HT2 receptor agonist. [2]

Contents

Use and effects

In his book PiHKAL , Alexander Shulgin lists a dosage of DON as being 3 to 4.5 mg orally with amphetamine-like stimulation and mild psychedelic effects lasting 8 to 15 hours. [1]

Pharmacology

DON acts as a serotonin 5-HT2A and 5-HT2C receptor partial agonist, albeit with far lower potency and efficacy than other DOx drugs. [2] It is also a serotonin 5-HT2B receptor partial agonist. [3] Earlier studies have also reported its affinities at serotonin receptors, including the serotonin 5-HT2 and 5-HT1 receptors. [4] [5] The drug produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents. [6]

Chemistry

DON is in a class of compounds commonly known as α-methyl phenethylamines, or amphetamines and the full chemical name is 1-(2,5-dimethoxy-4-nitrophenyl)propan-2-amine. It has a stereocenter.

Society and culture

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.[ citation needed ] 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

References

  1. 1 2 3 4 5 DON Entry in PiHKAL
  2. 1 2 Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP (June 2002). "Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors". Br J Pharmacol. 136 (4): 510–519. doi:10.1038/sj.bjp.0704747. PMC   1573376 . PMID   12055129.
  3. ↑ Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M (2023). "Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors". Frontiers in Pharmacology. 14 1101290. doi: 10.3389/fphar.2023.1101290 . PMC   9902381 . PMID   36762110.
  4. ↑ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID   3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  5. ↑ 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)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID   6479216.
  6. ↑ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152.
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