2,5-dimethoxy-4-bromoamphetamine

DOB
Chemical name	(4-bromo-2,5-Dimethoxy-amphetamine or 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane
Chemical formula	C11H16BrNO2
Molecular mass	274.15 g/mol
Melting point	63 - 65 °C 207 - 208 °C (hydrochloride)
CAS numbers	32156-26-6, 43061-15-0, 43061-16-1, 64638-07-9
SMILES	N[C@H](C)CC1=C(OC)C=C(Br)C(OC)=C1 (R-isomer)

DOB (or Bromo-DMA) is a psychedelic hallucinogenic drug of the phenethylamine class of compounds, sometimes used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967. The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(-)-DOB is the more active stereoisomer. In his book PIHKAL (Phenethylamines I Have Known and Loved), Shulgin lists the dosage range as 1 to 3 mg. DOB is generally taken orally. DOB is classified as a Schedule 1 substance in the United States, and is similarly controlled in other parts of the world. Internationally, DOB is a Schedule I drug under the Convention on Psychotropic Substances[1].

The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. According to Shulgin, the effects of DOB typically last 18 to 30 hours. Onset of the drug is also long, sometimes taking up to three hours.

Although rare on the black market, sales of DOB on blotter paper, misrepresented as LSD, and in tablet form, misrepresented as MDMA, have been reported.

External links

• DOB Entry in PIHKAL
• Erowid DOB Vault

Categorization