2,5-Dimethoxy-4-bromoamphetamine

DOB
INN: Brolamfetamine
	Chemical structure of (±)-DOB
	Ball-and-stick model of (R)-DOB
Clinical data
Other names	DOB; 4-Bromo-2,5-dimethoxyamphetamine; Brolamfetamine; Brolamphetamine; Bromo-DMA; 2,5-Dimethoxy-4-bromo-α-methylphenethylamine; 4-Bromo-2,5-dimethoxyphenyl-isopropylamine
Routes of; administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Onset of action	1–2 hours; Peak: 3–4 hours
Duration of action	18–36 hours
Identifiers
	IUPAC name 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	64638-07-9 (racemate); 43061-15-0 (R-isomer); 43061-16-1 (S-isomer);
PubChem CID	62065;
PubChem SID	46507989;
IUPHAR/BPS	155;
DrugBank	DB01484 ;
ChemSpider	55902 ;
UNII	67WJC4Y2QY;
KEGG	D12707;
ChEMBL	ChEMBL6607 ;
CompTox Dashboard (EPA)	DTXSID5050428 ;
Chemical and physical data
Formula	C11H16BrNO2
Molar mass	274.158 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	63–65 °C (145–149 °F) ; (207–208 °C hydrochloride)
	SMILES CC(CC1=CC(=C(C=C1OC)Br)OC)N;
	InChI InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 ; Key:FXMWUTGUCAKGQL-UHFFFAOYSA-N ;
	(verify)

2,5-Dimethoxy-4-bromoamphetamine (DOB), also known as brolamfetamine (INNTooltip International Nonproprietary Name), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. For many years, prior to the discovery of newer compounds, DOB was the most potent known phenethylamine psychedelic. It is taken orally.

The drug acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor. Analogues of DOB include 2C-B, DOM, DOI, and Bromo-DragonFLY (DOB-DFLY), among others.

DOB was first synthesized by Alexander Shulgin in 1967 and was described by him and his colleagues in the scientific literature in 1971. Shulgin subsequently further described the effects of DOB in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).