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;
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] is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.^[3] For many years, prior to the discovery of newer agents such as DOTFM, FLY compounds like Bromo-DragonFLY, and NBOMe compounds like 25I-NBOMe, DOB was the most potent known phenethylamine psychedelic.^[3]

The drug acts as an agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A receptor.^[4]^[5]

DOB was first synthesized by Alexander Shulgin in 1967 and was described by him and his colleagues in the scientific literature in 1971.^[6]^[7] Shulgin subsequently further described the effects of DOB in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[6]

^ Anvisa (24 July 2023). "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 25 July 2023). 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 Shulgin A (1981). "Profiles of Psychedelic Drugs: 10. DOB". J Psychoactive Drugs. 13 (1): 99. doi:10.1080/02791072.1981.10471457. PMID 7277091.
^ Cite error: The named reference Ray2010 was invoked but never defined (see the help page).
^ Cite error: The named reference RudinLuethiHoener2022 was invoked but never defined (see the help page).
^ ^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.

[1] Anvisa (24 July 2023). "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 25 July 2023). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[Organization2000-2] World Health Organization (2000). International Nonproprietary Names (INN) for Pharmaceutical Substances. World Health Organization. ISBN 978-0-11-986227-0.

[Shulgin1981-3] Shulgin A (1981). "Profiles of Psychedelic Drugs: 10. DOB". J Psychoactive Drugs. 13 (1): 99. doi:10.1080/02791072.1981.10471457. PMID 7277091.

[Ray2010-4] Cite error: The named reference Ray2010 was invoked but never defined (see the help page).

[RudinLuethiHoener2022-5] Cite error: The named reference RudinLuethiHoener2022 was invoked but never defined (see the help page).

[PiHKAL-6] Erowid Online Books: "PiHKAL" - #62 DOB

[ShulginSargentNaranjo1971-7] 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.

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