2,5-Dimethoxy-4-sec-butylamphetamine

2,5-Dimethoxy-4-sec-butylamphetamine (DOSB or DOSBu), also known as 1-(2,5-dimethoxy-4-(2-butyl)phenyl)-2-aminopropane (1-DBPAP), is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families.^[1][2][3][4]

DOSB

Clinical data
Other names	2,5-Dimethoxy-4-sec-butylamphetamine; 4-sec-Butyl-2,5-dimethoxyamphetamine; DOSB; DOSBu; 2,5-Dimethoxy-4-(2-butyl)amphetamine; 1-(2,5-dimethoxy-4-(2-butyl)phenyl)-2-aminopropane; 1-DBPAP
Routes of administration	Oral
Drug class	Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 1-(4-butan-2-yl-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	89556-71-8
PubChem CID	146057
ChemSpider	128843
ChEMBL	ChEMBL332535
CompTox Dashboard (EPA)	DTXSID101008866
Chemical and physical data
Formula	C15H25NO2
Molar mass	251.370 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C)C1=C(C=C(C(=C1)OC)CC(C)N)OC
InChI InChI=1S/C15H25NO2/c1-6-10(2)13-9-14(17-4)12(7-11(3)16)8-15(13)18-5/h8-11H,6-7,16H2,1-5H3 Key:VEQUTPSVRQTUHR-UHFFFAOYSA-N

Effects

In humans, DOSB is active at doses of 25 to 30 mg orally.^[3] Similarly to DOBU, it is said that there is a "strong stimulation factor, with real and long-lasting sleep disturbance".^[3] In a subsequent publication however, Alexander Shulgin stated that DOSB was inactive at 25 mg orally.^[4] David E. Nichols also said that DOSB was inactive at up to 10 mg orally.^[5]

Pharmacology

The affinity of DOSB for the rat serotonin 5-HT₂ receptor was about 7.8 nM.^[1][2][6] For comparison, the affinities of LSD and DOM in the same study were 6.31 nM and 18.6 nM, respectively.^[6] DOSB substitutes for LSD in rodent drug discrimination tests, albeit much less potently than DOM (ED₅₀Tooltip median effective dose = 1.80 mg/kg versus 0.148 mg/kg, respectively; ~12-fold difference) and with only partial generalization (70% versus 99%, respectively).^{[1][2][3][7][6]} However, in a subsequent study, full generalization was obtained.^[6]

Chemistry

DOSB is part of the series of straight-chain and branched-chain 4-alkylated DOx drugs that also includes DOM, DOET, DOPR, DOBU, DOAM, and DOHx, among others.^[4][8][9]

Some other notable analogues of DOSB include DOBU (n-butyl), DOIB (iso-butyl), and DOTB (sec-butyl).^{[1][2][10][11][5]}

DOIB, DOSB, and DOTB.^{[1][2][10][11][5]}

History

DOSB was first described in the scientific literature by 1984.^[7][5]