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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

Signal Word

Danger

Hazard Statements

H302,H310 + H330

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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.
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
Helena Carmo et al.
Toxicology, 206(1), 75-89 (2004-12-14)
4-Bromo-2,5-dimethoxyphenethylamine (2C-B) is a psychoactive designer drug of abuse that is sold under the street names "Venus", "Bromo", "Erox", "XTC" or "Nexus". Concern has been raised because only little is known about its toxicity and metabolism in humans. In the
Michael A Benneyworth et al.
Molecular pharmacology, 72(2), 477-484 (2007-05-29)
Recent clinical studies reveal that selective agonists of group II metabotropic glutamate (mGlu) receptors have robust efficacy in treating positive and negative symptoms in patients with schizophrenia. Group II mGlu receptor agonists also modulate the in vivo activity of psychotomimetic
Katerina Beránková et al.
Forensic science international, 170(2-3), 94-99 (2007-07-17)
2,5-Dimethoxy-4-bromoamphetamine (DOB) is one of the potent hallucinogenic phenylalkylamines, whose ingestion has already caused several deaths reported all over the world. However, there is insufficient information on DOB properties based on controlled pharmacokinetic studies available. The aim of this study
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