2,5-Dimethoxy-4-butylamphetamine

2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), only low dosages of 2–3 mg were tested, with the duration simply listed as "very long". DOBU produces paresthesia and difficulty sleeping, but with few other effects. Compared to shorter chain homologues such as DOM, DOET and DOPR which are all potent hallucinogens, DOBU has an even stronger 5-HT2 binding affinity but fails to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting it has low efficacy and is thus an antagonist or weak partial agonist at the 5-HT2A receptor.

"DOBU" redirects here. For other uses, see Dobu (disambiguation).
2,5-Dimethoxy-4-butylamphetamine
Names
Preferred IUPAC name
1-(4-Butyl-2,5-dimethoxyphenyl)propan-2-amine
Other names
2,5-Dimethoxy-4-butyl-amphetamine
2,5-Dimethoxy-4-butyl-1-ethyl-(alpha-methyl)amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H25NO2/c1-5-6-7-12-9-15(18-4)13(8-11(2)16)10-14(12)17-3/h9-11H,5-8,16H2,1-4H3 Y
    Key: NGVDYAULSQKEGW-UHFFFAOYSA-N Y
  • InChI=1/C15H25NO2/c1-5-6-7-12-9-15(18-4)13(8-11(2)16)10-14(12)17-3/h9-11H,5-8,16H2,1-4H3
    Key: NGVDYAULSQKEGW-UHFFFAOYAF
SMILES
  • C1(=CC(=C(C=C1CC(C)N)OC)CCCC)OC
  • O(c1cc(c(OC)cc1CC(N)C)CCCC)C
Properties
C15H25NO2
Molar mass 251.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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