2,5-Dimethoxy-4-bromoamphetamine

2,5-Dimethoxy-4-bromoamphetamine

(R)-isomer
Names
IUPAC name 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane
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
ChEMBL	ChEMBL6607 Y
ChemSpider	55902 Y
DrugBank	DB01484 Y
IUPHAR/BPS	155
Jmol 3D model	Interactive image
PubChem	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)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (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.

Chemistry

Tabs of DOB, confiscated by police in Concord, California in 2006.

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.

Pharmacology

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.

It has been suggested that DOB is a prodrug metabolized in the lungs.

Legal status

Internationally DOB is a Schedule I drug under the Convention on Psychotropic Substances.

Canada

Listed as a Schedule 1 as it is an analogue of amphetamine.

Australia

DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.

See also

• 2,5-Dimethoxy-4-Substituted Amphetamines
• 2C-B - the alpha-desmethyl derivative of DOB

External links

• DOB Entry in PiHKAL
• DOB Entry in PiHKAL • info
• Erowid DOB Vault