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 2–3 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-HT_2A receptor.^[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): 1032–6. doi:10.1021/jm00165a023. PMID 2308135.

[pmid2308135-1] 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): 1032–6. doi:10.1021/jm00165a023. PMID 2308135.

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