Grundinformationen
- Standard-SMILES
Br.NCCc1cc(O)c(O)cc1O- InChIKey
MLACDGUOKDOLGC-UHFFFAOYSA-N- Summenformel
- C8H12BrNO3
- Durchschnittliche Molmasse
- 250,09 g/mol
- Monoisotopische Masse
- 249,00005534
Überblick
See also: 6-Hydroxydopamine (annotation moved to); Hydroxydopamine (annotation moved to).
Namen und Bezeichner
- Bevorzugter Name
- 1,2,4-Benzenetriol, 5-(2-aminoethyl)-, hydrobromide (1:1)
- IUPAC
- 5-(2-aminoethyl)benzene-1,2,4-triol;hydrobromide
- Lokaler Name
- 5-(2-Aminoethyl)-4-hydroxypyrocatechinhydrobromid
- Englischer Name
- 6-HYDROXYDOPAMINE HYDROBROMIDE
- Summenformel
- C8H12BrNO3
- Molmasse
- 250.09
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
636-00-0- PubChem CID
- 176170
- DTXSID
DTXSID30212972- ChEMBL
CHEMBL1718398- UNII
- TWC1D4W0WB
- EC Number
- 211-247-0
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 86,7 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 142
Physikochemische Eigenschaften
- Schmelzpunkt
- 216 · 216-220 °C(lit.)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly), Water (Slightly)
- Aggregatzustand
- solid
- Farbe
- tan to brown
- BRN
- 3713280 · 3713280
- Stabilität
- Hygroscopic, Light Sensitive
- InChI
- InChI=1S/C8H11NO3.BrH/c9-2-1-5-3-7(11)8(12)4-6(5)10;/h3-4,10-12H,1-2,9H2;1H
- InChIKey
- MLACDGUOKDOLGC-UHFFFAOYSA-N
- SMILES
- C(C1C=C(O)C(O)=CC=1O)CN.Br
- CAS Datenbank
- 636 · 636-00-0(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Sicherheitsdaten
- F
- 3-10
- wgk
- 3
- RTECS-Nr.
- DC4600000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.
Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters.
Anwendungen
Beschreibung6-OHDA is a catecholaminergic neurotoxin that has been used to induce dopaminergic lesions and parkinsonian symptoms as a model of Parkinson''s disease in rodents. It induces locomotor impairment in mice and loss of tyrosine hydroxylase-reactive neurons in mouse brain when administered into the substantia nigra, medial forebrain bundle (MFB), or striatum at doses of 9, 6, and 18 μg, respectively. Intracisternal administration of 6-OHDA (200 μg) decreases dopamine and norepinephrine levels in rat brain. It induces apoptosis in primary rat cortical cells and PC12 rat adrenal cells when used at a concentration of 50 μM. 6-OHDA (75 μM) activates caspase-3, -8, and -9 in a time-dependent manner and increases the level of intracellular reactive oxygen species (ROS) in PC12 cells and induces apoptosis in rat substantia nigra when stereotaxically injected into the right MFB.
Verwenden6-Hydroxydopamine is a selective catecholaminergic neurotoxin. Studies show that 6-Hydroxydopamine can be used to create an animal model of Parkinson''s disease as it causes almost complete destruction of nigral dopaminergic neurons and their striatal terminals when injected into the substantia nigra of rats. 6-Hydroxydopamine induces apoptosis in PC12 cells.
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