2,5-Dimethoxy-4-bromoamphetamine

2,5-Dimethoxy-4-bromoamphetamine

(R)-isomer
Names
IUPAC name 1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine
Other names 4-Bromo-2,5-dimethoxy-amphetamine
Identifiers
CAS Number	64638-07-9 (racemate) N 43061-15-0 (R) N 43061-16-1 (S) N
3D model (Jmol)	Interactive image
ChemSpider	55902 Y
DrugBank	DB01484 Y
IUPHAR/BPS	155
PubChem CID	62065
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 Y Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N Y InChI=1/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-UHFFFAOYAD
SMILES Brc1cc(OC)c(cc1OC)CC(N)C
Properties
Chemical formula	C11H16BrNO2
Molar mass	274.15 g/mol
Melting point	63 to 65 °C (145 to 149 °F; 336 to 338 K) (207–208 °C hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) 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.

The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(–)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors, making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.

DOB is a 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT₂ receptor subfamily. It is an agonist of human TAAR1.