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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
Structure of BROLAMFETAMINE HYDROBROMIDE

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

effective dose of 2 mg for an 80 kg man
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:04:35 GMT 2023
Edited
by admin
on Sat Dec 16 08:04:35 GMT 2023
Record UNII
1S6K9S6785
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROLAMFETAMINE HYDROBROMIDE
Common Name English
BENZENEETHANAMINE, 4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYL-, HYDROBROMIDE (1:1)
Systematic Name English
BENZENEETHANAMINE, 4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYL-, HYDROBROMIDE, (±)-
Systematic Name English
DOB HYDROBROMIDE
Common Name English
Code System Code Type Description
FDA UNII
1S6K9S6785
Created by admin on Sat Dec 16 08:04:35 GMT 2023 , Edited by admin on Sat Dec 16 08:04:35 GMT 2023
PRIMARY
CAS
53581-53-6
Created by admin on Sat Dec 16 08:04:35 GMT 2023 , Edited by admin on Sat Dec 16 08:04:35 GMT 2023
PRIMARY
PUBCHEM
62064
Created by admin on Sat Dec 16 08:04:35 GMT 2023 , Edited by admin on Sat Dec 16 08:04:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID7049001
Created by admin on Sat Dec 16 08:04:35 GMT 2023 , Edited by admin on Sat Dec 16 08:04:35 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE