2,5-Dimethoxy-4-butylamphetamine

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
CAS Number	63779-89-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL8214 ;
ChemSpider	8236274 ;
PubChem CID	10060720;
UNII	6ARH6DPN4N ;
CompTox Dashboard (EPA)	DTXSID90434976 ;
	InChI 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 Key: NGVDYAULSQKEGW-UHFFFAOYSA-N ; 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
Chemical formula	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). verify (what is ?) Infobox references

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 to 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 serotonin 5-HT₂ receptor affinity, but fails to substitute for hallucinogens in animal drug discrimination tests or produce hallucinogenic effects in humans.^[1] These findings suggest that it has low efficacy and is thus an antagonist or weak partial agonist at the serotonin 5-HT_2A receptor. However, DOBU has since been found to act as a full agonist of the serotonin 5-HT_2A receptor.^[2] Hence, the reasons for the lack of psychedelic effects with DOBU remain unknown.^[2] DOBU is inactive as an agonist of the serotonin 5-HT_2B receptor though still shows affinity for the serotonin 5-HT_2C receptor.^[2]

Isomers

Alternative isomers of DOBU can also be produced, where the 4-(n-butyl) group of DOBU is replaced with any of the three other butyl isomers, the iso-butyl, sec-butyl and tert-butyl compounds being called DOIB, DOSB, and DOTB, respectively.^[3]^[4]^[5] All are significantly less potent than DOBU, with DOIB being active at around 10–15 mg, and DOSB at 25–30 mg, and both being primarily stimulant in action with little or no psychedelic effects.^[3]^{[additional citation(s) needed]} The most highly branched isomer DOTB was completely inactive in both animal and human trials.^[3]^{[additional citation(s) needed]} However, it was also reported that DOTB and DOAM partially generalized to DOM in animal drug discrimination tests.^[6]

References

^ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". Journal of Medicinal Chemistry. 33 (3): 1032–1036. doi:10.1021/jm00165a023. PMID 2308135.
^ ^a ^b ^c Luethi, Dino; Rudin, Deborah; Hoener, Marius C.; Liechti, Matthias E. (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines" (PDF). The FASEB Journal. 36 (S1). doi:10.1096/fasebj.2022.36.S1.R2691. ISSN 0892-6638.
^ ^a ^b ^c ^d Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. pp. 95–142.
^ ^a ^b Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795.
^ ^a ^b Shulgin, Alexander T. (2003). "Basic Pharmacology and Effects". In Laing, Richard R. (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
^ Glennon RA, Young R, Rosecrans JA (April 1982). "A comparison of the behavioral effects of DOM homologs". Pharmacol Biochem Behav. 16 (4): 557–559. doi:10.1016/0091-3057(82)90414-2. PMID 7071089.

External links

[SeggelYousifLyon1990-1] Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". Journal of Medicinal Chemistry. 33 (3): 1032–1036. doi:10.1021/jm00165a023. PMID 2308135.

[LuethiRudinHoener2022-2] Luethi, Dino; Rudin, Deborah; Hoener, Marius C.; Liechti, Matthias E. (2022). "Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines" (PDF). The FASEB Journal. 36 (S1). doi:10.1096/fasebj.2022.36.S1.R2691. ISSN 0892-6638.

[NicholsGlennon1984-3] Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. pp. 95–142.

[JacobShulgin1994-4] Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795.

[Shulgin2003-5] Shulgin, Alexander T. (2003). "Basic Pharmacology and Effects". In Laing, Richard R. (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.

[GlennonYoungRosecrans1982-6] Glennon RA, Young R, Rosecrans JA (April 1982). "A comparison of the behavioral effects of DOM homologs". Pharmacol Biochem Behav. 16 (4): 557–559. doi:10.1016/0091-3057(82)90414-2. PMID 7071089.

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2,5-Dimethoxy-4-butylamphetamine

Isomers

See also

References

External links

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