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D7412

Sigma-Aldrich

(±)-2,5-Dimethoxy-4-bromoamphetamine hydrobromide

Synonym(s):

(±)-DOB hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C11H16BrNO2 · HBr
CAS Number:
53581-53-6
Molecular Weight:
355.07
MDL number:
MFCD00069251
UNSPSC Code:
12352116
PubChem Substance ID:
24894134
NACRES:
NA.77

drug control

USDEA Schedule I; Home Office Schedule 1; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIA (Portugal)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
veterinary

SMILES string

Br[H].COc1cc(CC(C)N)c(OC)cc1Br

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Biochem/physiol Actions

Hallucinogenic; 5-HT2 serotonin receptor agonist.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 4 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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M Titeler et al.
Biochemical pharmacology, 36(19), 3265-3271 (1987-10-01)
The affinities of putative serotonin receptor agonists and antagonists for 5-HT1A, 5-HT1B, 5-HT1C, and 5-HT2 receptors were assayed using radioligand binding assays. The 5-HT1 sites were labeled with the agonist radioligands [3H]-8-hydroxy-2-(di-n-propylamino)-tetralin [3H]-8-OH-DPAT, [3H]-5-HT, and [3H]mesulergine. The 5-HT2 receptor was
W A Heller et al.
European journal of pharmacology, 138(1), 115-117 (1987-06-12)
DOB, 4-bromo-2,5-dimethyloxyamphetamine, a potent hallucinogen, displays high affinity for the 5-HT2 receptor in binding assays. Since 5-HT contractile responses in guinea pig trachea are mediated by 5-HT2 receptors, we assessed the activity of DOB and related analogs in this preparation.
Marie Balíková
Forensic science international, 153(1), 85-91 (2005-06-28)
2,5-Dimethoxy-4-bromoamphetamine (DOB) is a strongly acting hallucinogen with an estimated effective dose of 2 mg for an 80 kg man. The case of two men who ingested a new "hallucinogen LSD-like" designer drug is reported here. They experienced intense hallucinations
Danielle M Schultz et al.
Bioorganic & medicinal chemistry, 16(11), 6242-6251 (2008-05-10)
Phenylalkylamines that possess conformationally rigidified furanyl moieties in place of alkoxy arene ring substituents have been shown previously to possess the highest affinities and agonist functional potencies at the serotonin 5-HT(2A) receptor among this chemical class. Further, affinity declines when
R S Westphal et al.
Molecular pharmacology, 46(5), 937-942 (1994-11-01)
Expression of the 5-hydroxytryptamine type 2C (5-HT 2C) receptor in NIH/3T3 fibroblasts results in agonist-independent 5-HT2C receptor activation. Some 5-HT2c receptor antagonists decrease this activation and are termed inverse agonists. The present study uses this system to evaluate functional and
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