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Details

Stereochemistry RACEMIC
Molecular Formula C11H16BrNO2.ClH
Molecular Weight 310.615
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROLAMFETAMINE HYDROCHLORIDE

SMILES

Cl.COC1=CC(Br)=C(OC)C=C1CC(C)N

InChI

InChIKey=SPBBKPOIDQIWDZ-UHFFFAOYSA-N
InChI=1S/C11H16BrNO2.ClH/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 ClH
Molecular Weight 36.461
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
Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.
1996 Jan 12
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
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 10:21:27 GMT 2023
Edited
by admin
on Sat Dec 16 10:21:27 GMT 2023
Record UNII
OII49KV8F3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROLAMFETAMINE HYDROCHLORIDE
Common Name English
(±)-1-(4-BROMO-2,5-DIMETHOXYPHENYL)-2-AMINOPROPANE HYDROCHLORIDE
Systematic Name English
BROLAMFETAMINE HYDROCHLORIDE [INCB:GREEN LIST]
Common Name English
PHENETHYLAMINE, 4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE
Systematic Name English
4-bromo-2,5-DMA hydrochloride
Common Name English
4-BROMO-2,5-DIMETHOXYAMPHETAMINE HYDROCHLORIDE
Systematic Name English
DOB HYDROCHLORIDE
Common Name English
BENZENEETHANAMINE, 4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
CAYMAN
11142
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
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INCB IDS CODE
PD 009
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
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EPA CompTox
DTXSID1048883
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
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PUBCHEM
12626562
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
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CAS
29705-96-2
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
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FDA UNII
OII49KV8F3
Created by admin on Sat Dec 16 10:21:27 GMT 2023 , Edited by admin on Sat Dec 16 10:21:27 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE