2,5-Dimethoxy-4-bromoamphetamine

Dimethoxybromoamphetamine
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; 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)^[2] 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.^[3]^[4] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.^[3]

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ World Health Organization (2000). International Nonproprietary Names (INN) for Pharmaceutical Substances. World Health Organization. ISBN 978-0-11-986227-0.
^ ^a ^b Erowid Online Books: "PiHKAL" - #62 DOB
^ Shulgin AT, Sargent T, Naranjo C (1971). "4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog". Pharmacology. 5 (2): 103–107. doi:10.1159/000136181. PMID 5570923. S2CID 46844380.