Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H16BrNO2 |
| Molecular Weight | 274.154 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(Br)=C(OC)C=C1CC(C)N
InChI
InChIKey=FXMWUTGUCAKGQL-UHFFFAOYSA-N
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
| Molecular Formula | C11H16BrNO2 |
| Molecular Weight | 274.154 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Brolamfetamine (also known as DOB, bromo-DMA, and 4-bromo-2,5-dimethoxyphenylisopropylamine) is one of a vast number of compounds used recreationally to achieve hallucinogenic effects. Brolamfetamine is one of the most potent hallucinogens, with its hallucinogenic potency directly linked to its abuse potential. Brolamfetamine acts as a partial agonist of 5HT2A, 5HT2B, 5HT2C, and TAAR1 receptors, but it’s psychedelic effects are mainly mediated by its agonistic properties at the 5-HT2A receptor. Animal studies have shown physiologic effects including hypertension, tachycardia, hyperpyrexia, pupillary dilatation, and peripheral vasoconstriction. In general, Brolamfetamine having a similar effect to LSD, with slower onset (up to 3–4 h to peak intoxication) and longer duration of effect (up to 36 h). Brolamfetamine is not commonly available, through periods of higher circulation were reported in Australia in 1983, Ireland in 2003, and in Italy in 2015. Brolamphetamine, as well as many other synthetic hallucinogens, are increasingly being sold as LSD. Internationally Brolamfetamine is a Schedule I drug under the Convention on Psychotropic Substances. Due to its selectivity, Brolamfetamine is often used in scientific research when studying the 5-HT2 receptor subfamily.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose. | 2005-10-04 |
|
| Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. | 2004-11-18 |
|
| Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004-08 |
|
| Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists. | 2001-10 |
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| 1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character. | 2001-09-27 |
|
| Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors. | 2000-02 |
|
| Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. | 1999-01 |
|
| Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs. | 1998-07 |
|
| Activating mutations of the serotonin 5-HT2C receptor. | 1997-09 |
|
| Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities. | 1996-01-12 |
|
| Serotonergic involvement in haloperidol-induced catalepsy. | 1993-04 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15979834
effective dose of 2 mg for an 80 kg man
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:13:08 GMT 2025
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Mon Mar 31 18:13:08 GMT 2025
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| Record UNII |
67WJC4Y2QY
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Validated (UNII)
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Designer-drugs-2,5-Dimethoxy-4-bromoamphetamine
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DEA NO. |
7391
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C47794
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PiHKAL
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CHEMBL6607
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5874
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100000088651
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2,5-Dimethoxy-4-bromoamphetamine
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C80757
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DTXSID5050428
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62065
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PD 009
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SUB05903MIG
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |
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