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
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 |
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Serotonergic involvement in haloperidol-induced catalepsy. | 1993 Apr |
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Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs. | 1998 Jul |
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Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. | 1999 Jan |
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Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004 Aug |
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Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. | 2004 Nov 18 |
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Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose. | 2005 Oct 4 |
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
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WIKIPEDIA |
Designer-drugs-2,5-Dimethoxy-4-bromoamphetamine
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DEA NO. |
7391
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NCI_THESAURUS |
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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64638-07-9
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67WJC4Y2QY
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SUB05903MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)