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D7412

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

Name: (±)-2,5-Dimethoxy-4-bromoamphetamine hydrobromide
Brand: SIGMA

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

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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

GHS06

signalword

Danger

hcodes

H302,H310 + H330

pcodes

P260 - P262 - P280 - P301 + P312 - P302 + P352 + P310 - P304 + P340 + P310

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

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Selectivity of serotonergic drugs for multiple brain serotonin receptors. Role of [3H]-4-bromo-2,5-dimethoxyphenylisopropylamine ([3H]DOB), a 5-HT2 agonist radioligand.

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

Potent agonist activity of DOB at 5-HT2 receptors in guinea pig trachea.

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.

Direct injection of 5-HT2A receptor agonists into the medial prefrontal cortex produces a head-twitch response in rats.

D L Willins et al.

The Journal of pharmacology and experimental therapeutics, 282(2), 699-706 (1997-08-01)

The serotonin (5-HT)(2A/2c) agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI), the 5-HT2C agonist 6-chloro-2-[1-piperazinyl]-pyrazine and the 5-HT2A partial agonist m-chloro-phenylpiperazine (mCPP) were injected bilaterally into the medial prefrontal cortex of male rats. DOI and mCPP, but not 6-chloro-2-[1-piperazinly]-pyrazine, elicited a dose-dependent head-twitch response (HTR).

Radiolabelling of the human 5-HT2A receptor with an agonist, a partial agonist and an antagonist: effects on apparent agonist affinities.

A J Sleight et al.

Biochemical pharmacology, 51(1), 71-76 (1996-01-12)

Previous work has shown that 5-hydroxytryptamine (5-HT)2A receptors can be radiolabelled with various radioligands, including partial agonists, such as [125I]-DOI and [3H]-DOB, and antagonists, such as [3H]-ketanserin and [3H]-spiperone. Because 5-HT has high affinity for the 5-HT2A receptor when displacing

'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.

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

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