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
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;
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)

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INNTooltip International Nonproprietary Name) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.