# 2,5-Dimethoxy-4-bromoamphetamine

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INNTooltip International Nonproprietary Name) 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 drug acts as a serotonin 5-HT$_2$ receptor agonist.

## Chemistry

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.

## Side effects

Excessively high doses of DOB may cause diffuse arterial spasm. The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.

## Pharmacology
### Pharmacodynamics

DOB activities :
| Target | Affinity (K$_i$, nM) |
| 5-HT$_{1A}$ | 2,550–6,327 |
| 5-HT$_{1B}$ | 941 |
| 5-HT$_{1D}$ | 636 |
| 5-HT$_{1E}$ | 556–1,427 |
| 5-HT$_{1F}$ | ND |
| 5-HT$_{2A}$ | 0.6–81 (K$_i$) 0.52–50 (EC$_{50}$Tooltip half-maximal effective concentration) 57–97% (E$_{max}$Tooltip maximal efficacy) |
| 5-HT$_{2B}$ | 2.9–44 |
| 5-HT$_{2C}$ | 1.3–60 (K$_i$) 0.25–102 (EC$_{50}$) 58–112% (E$_{max}$) |
| 5-HT$_3$ | >10,000 |
| 5-HT$_4$ | ND |
| 5-HT$_{5A}$ | 5,311 |
| 5-HT$_6$ | 5,535 |
| 5-HT$_7$ | 506 |
| α$_{1A}$, α$_{1B}$ | >10,000 |
| α$_{1D}$ | ND |
| α$_{2A}$ | 4,266 |
| α$_{2B}$ | 1,527 |
| α$_{2C}$ | 594 |
| β$_1$ | 2,425 |
| β$_2$ | 303 |
| D$_1$, D$_2$ | >10,000 |
| D$_3$ | 808 |
| D$_4$, D$_5$ | >10,000 |
| H$_1$ | 9,120 |
| H$_2$–H$_4$ | >10,000 |
| M$_1$, M$_2$ | >10,000 |
| M$_3$ | 1,152 |
| M$_4$, M$_5$ | >10,000 |
| TAAR$_1$ | >1,000 |
| I$_1$ | 1,596 |
| σ$_1$ | 2,193 |
| σ$_2$ | >10,000 |
| SERTTooltip Serotonin transporter | 8,538 (K$_i$) |
| NETTooltip Norepinephrine transporter | >10,000 (K$_i$) |
| DATTooltip Dopamine transporter | >10,000 (K$_i$) |
| MAO-ATooltip Monoamine oxidase A | 100,000 (IC$_{50}$Tooltip half-maximal inhibitory concentration) (rat) |
| MAO-BTooltip Monoamine oxidase B | >100,000 (IC$_{50}$) (rat) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: ||
DOB is a serotonin 5-HT$_{2A}$, 5-HT$_{2B}$, and 5-HT$_{2C}$ receptor 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-HT$_2$ receptor subfamily.
It is a very weak agonist of the human trace amine-associated receptor 1 (TAAR1) and a weak agonist of the rhesus monkey TAAR1. In contrast to the serotonin releasing agent MDMA, DOB does not produce protein kinase C (PKC) activation in the brains of rodents in vivo. The PKC activation by MDMA appears to be dependent on uptake by the serotonin transporter (SERT).
DOB has been found to reduce aggression in rats.

## History

DOB was first synthesized by Alexander Shulgin in 1967. It was first described in the scientific literature in a paper by Shulgin, Claudio Naranjo, and another colleague in 1971. The INNTooltip International Nonproprietary Name of DOB, brolamfetamine, was proposed and recommended by the World Health Organization (WHO) in 1986. This was the same year that the Multidisciplinary Association for Psychedelic Studies (MAPS) was founded. DOB was registered with the WHO as a supposed "anorexic" (appetite suppressant).

## Society and culture
### Legal status

Internationally, DOB is a Schedule I substance under the Convention on Psychotropic Substances and the drug is legal only for medical, industrial or scientific purposes.

#### 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 (February 2017). 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.

#### Russia

Schedule I, possession of at least 10 mg is a criminal offence.

#### United Kingdom

DOB is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971.

#### United States

DOB is a Schedule I controlled substance under federal law in the United States. It was scheduled in 1973.