2,5-Dimethoxy-4-amylamphetamine

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2,5-Dimethoxy-4-amylamphetamine
DOAM.png
DOAM molecule
Names
IUPAC name
2-(2,5-Dimethoxy-4-pentyl-phenyl)-1-methyl-ethylamine
Other names
2,5-Dimethoxy-4-amyl-amphetamine;
2,5-Dimethoxy-4-amyl-1-ethyl-(alpha-methyl)amine
Identifiers
63779-90-8 N
Abbreviations DOAM
ChEMBL ChEMBL161416 YesY
ChemSpider 10440619 YesY
Jmol 3D model Interactive image
Interactive image
  • InChI=1S/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3 YesY
    Key: VLJORLCVOAUUKM-UHFFFAOYSA-N YesY
  • InChI=1/C16H27NO2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12H,5-9,17H2,1-4H3
    Key: VLJORLCVOAUUKM-UHFFFAOYAN
  • CCCCCC1=CC(OC)=C(CC(C)N)C=C1OC
  • COc1cc(CCCCC)c(cc1CC(C)N)OC
Properties
C16H27NO2
Molar mass 265.39 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. DOAM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the 5-HT2 binding affinity increases, rising to a maximum with the 4-(n-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than n-propyl, or with other bulky groups such as isopropyl, t-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low efficacy and are thus antagonists or weak partial agonists at the 5-HT2A receptor.[1][2][3]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.

See also

External links

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