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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
Structure of BROLAMFETAMINE

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

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 ( + / - )

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
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
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 Fri Dec 15 15:55:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:05 GMT 2023
Record UNII
67WJC4Y2QY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROLAMFETAMINE
INCB:GREEN LIST   INN   MART.  
INN  
Official Name English
J275.083J
Code English
BENZENEETHANAMINE, 4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYL-
Systematic Name English
BROLAMFETAMINE [INCB GREEN LIST]
Common Name English
BROMO-DMA
Common Name English
4-BROMO-2,5-DIMETHOXY-AMPHETAMINE
Systematic Name English
1-(4-BROMO-2,5-DIMETHOXYPHENYL)PROPAN-2-AMINE
Systematic Name English
DOB
Common Name English
brolamfetamine [INN]
Common Name English
(±)-4-BROMO-2,5-DIMETHOXY-.ALPHA.-METHYLPHENETHYLAMINE
Systematic Name English
BROLAMFETAMINE [MART.]
Common Name English
2,5-DIMETHOXY-4-BROMOAMPHETAMINE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-2,5-Dimethoxy-4-bromoamphetamine
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
DEA NO. 7391
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
WIKIPEDIA PiHKAL
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL6607
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
INN
5874
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
SMS_ID
100000088651
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
WIKIPEDIA
2,5-Dimethoxy-4-bromoamphetamine
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
NCI_THESAURUS
C80757
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID5050428
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
PUBCHEM
62065
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
INCB IDS CODE
PD 009
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
CAS
64638-07-9
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
FDA UNII
67WJC4Y2QY
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
EVMPD
SUB05903MIG
Created by admin on Fri Dec 15 15:55:05 GMT 2023 , Edited by admin on Fri Dec 15 15:55:05 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY