Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H16BrNO2.BrH |
Molecular Weight | 355.066 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.COC1=CC(Br)=C(OC)C=C1CC(C)N
InChI
InChIKey=KOUBEZAODVTFTG-UHFFFAOYSA-N
InChI=1S/C11H16BrNO2.BrH/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2;/h5-7H,4,13H2,1-3H3;1H
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 | ( + / - ) |
Molecular Formula | BrH |
Molecular Weight | 80.912 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Serotonergic involvement in haloperidol-induced catalepsy. | 1993 Apr |
|
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities. | 1996 Jan 12 |
|
Activating mutations of the serotonin 5-HT2C receptor. | 1997 Sep |
|
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs. | 1998 Jul |
|
Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. | 1999 Jan |
|
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 Feb |
|
Multiple conformations of native and recombinant human 5-hydroxytryptamine(2a) receptors are labeled by agonists and discriminated by antagonists. | 2001 Oct |
|
1-[2-methoxy-5-(3-phenylpropyl)]-2-aminopropane unexpectedly shows 5-HT(2A) serotonin receptor affinity and antagonist character. | 2001 Sep 27 |
|
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004 Aug |
|
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. | 2004 Nov 18 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:04:35 GMT 2023
by
admin
on
Sat Dec 16 08:04:35 GMT 2023
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Record UNII |
1S6K9S6785
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Record Status |
Validated (UNII)
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Record Version |
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1S6K9S6785
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53581-53-6
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62064
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DTXSID7049001
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admin on Sat Dec 16 08:04:35 GMT 2023 , Edited by admin on Sat Dec 16 08:04:35 GMT 2023
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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