Grundinformationen
- Standard-SMILES
ClCCN(Cc1ccccc1)Cc1ccccc1- InChIKey
GSLWSSUWNCJILM-UHFFFAOYSA-N- Summenformel
- C16H18ClN
- Durchschnittliche Molmasse
- 259,77 g/mol
- Monoisotopische Masse
- 259,11277726
Namen und Bezeichner
- Bevorzugter Name
- N-(2-Chloroethyl)dibenzylamine
- IUPAC
- N,N-dibenzyl-2-chloroethanamine
- Englischer Name
- Dibenamine
- Summenformel
- C16H18ClN
- Molmasse
- 259.77
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
51-50-3- PubChem CID
- 5820
- DTXSID
DTXSID20199001- ChEMBL
CHEMBL3305685- UNII
- 43EXU2S56H
- Nikkaji
- J10.688G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,8
- Polarare Oberfläche (TPSA)
- 3,2 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 187
Experimentelle und physikochemische Eigenschaften
Stability/Shelf Life
TURNS YELLOW ON STORAGE & DECOMP ON STANDING TO FORM SOLID POLYMERIC COMPD /CHLOROETHYLAMINES/
STABLE IN ACID SOLN BUT RAPIDLY LOSES ACTIVITY IN NEUTRAL OR ALKALINE AQ SOLUTIONS /HYDROCHLORIDE/
Other Experimental Properties
MP: 192 °C, ALSO GIVEN AS 180-181 °C; PRACTICALLY INSOL IN H2O NEAR NEUTRALITY; SOLUBLE IN DIL ACID: 2% @ PH 2.1, 1% @ PH 2.4, 0.5% @ PH 2.74; SOL IN 95% ALCOHOL, PROPYLENE GLYCOL /HYDROCHLORIDE/
COLORLESS CRYSTALLINE SOLID /CHLOROETHYLAMINE HYDROCHLORIDE/
Physikochemische Eigenschaften
- Schmelzpunkt
- 192 °C · 192 °C
- Siedepunkt
- 407.11 °C · 407.11°C (rough estimate)
- Dichte
- 1.0738 · 1.0738 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- pka
- 6.5 · 6.50±0.50(Predicted)
Sicherheit und Regulatorisches
Toxikologische Informationen
Interactions
...ATROPINE APPEARS TO ANTAGONIZE ACTION OF DIBENAMINE OR "DEBLOCK".
REDN IN PRESSOR RESPONSE WITHOUT REVERSAL IS USUALLY SEEN WHEN CAPACITY FOR ADRENERGIC VASODILATATION IS LIMITED BY ANY FACTOR, FOR EXAMPLE, SYMPATHOMIMETIC AMINE USED (NOREPINEPHRINE, PHENYLEPHRINE, OR OTHER AGENTS WITH MINIMAL BETA-ADRENERGIC AGONISTIC ACTIVITY) OF PREPN EMPLOYED...
FORMATION OF 7% FORMALADHYDE INDUCED SC GRANULOMA WAS GREATLY SUPPRESSED BY EPINEPHRINE & SLIGHTLY BY NOREPINEPHRINE. DIBENAMINE WAS A WEAKER EXPTL GRANULOMA SUPPRESSOR.
CENTRAL EFFECTS OF SOME ADRENOLYTICS ON SPONTANEOUS MOTILITY & ON POTENTIATION OF SUBHYPNOTIC DOSES OF SODIUM PENTOBARBITAL WERE STUDIED IN MICE. DIBENAMINE POTENTIATED THE ACTION OF SODIUM PENTOBARBITAL. ALL DRUGS, EXCEPT BRETYLIUM DECR SPONTANEOUS MOTILITY.
For more Interactions (Complete) data for DIBENAMINE (9 total), please visit the HSDB record page.
Human Toxicity Excerpts
DIBENAMINE.../STIMULATES/ CNS TO CAUSE NAUSEA, VOMITING, HYPERVENTILATION, MOTOR EXCITABILITY...CONVULSIONS, PARTICULARLY WHEN RELATIVELY LARGE DOSE IS RAPIDLY INJECTED IV. IN MAN, CHARACTERISTIC LOSS OF TIME PERCEPTION MAY OCCUR.
LOSS OF VASOMOTOR CONTROL CAN RESULT IN POSTURAL HYPOTENSION & REFLEX TACHYCARDIA IN AMBULATORY PATIENTS, OR A SHARP FALL IN BLOOD PRESSURE IN THOSE WHO ARE HYPOVOLEMIC. /ALPHA-ADRENERGIC BLOCKING AGENTS/
OTHER RESULTS OF ALPHA-RECEPTOR BLOCKADE INCL MIOSIS, NASAL STUFFINESS, & INHIBITION OF EJACULATION. /ALPHA-ADRENERGIC BLOCKING AGENTS/
Non-Human Toxicity Excerpts
...TACHYCARDIA IN INTACT ANIMALS IS USUALLY EXAGGERATED BECAUSE PRESSOR RESPONSE IS PREVENTED & REFLEX VAGAL STIMULATION IS MINIMIZED. ...DIBENAMINE INDUCE/S/ REFLEX TACHYCARDIA...
BOVINE BRAIN SODIUM-POTASSIUM ACTIVATED ATPASE WAS IRREVERSIBLY INHIBITED BY DIBENAMINE & DIBENAMINE ANALOGS WHICH ARE ADRENERGIC ALPHA-BLOCKERS.
Sicherheitsdaten
- Giftige Stoffe Daten
- 51-50-3(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
ALPHA-ADRENERGIC BLOCKING AGENTS BIND SELECTIVELY TO ALPHA CLASS OF ADRENERGIC RECEPTORS & THEREBY INTERFERE WITH CAPACITY OF SYMPATHOMIMETIC AMINES TO INITIATE ACTIONS AT THESE SITES. ...DIBENAMINE BIND/S/ COVALENTLY TO ALPHA RECEPTOR & PRODUCE/S/ IRREVERSIBLE & INSURMOUNTABLE TYPE OF BLOCKADE.
...DIBENAMINE HAS RELATIVELY LOW ANTIHISTAMINIC ACTIVITY...
MeSH Pharmacological Classification
Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
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.
Verwendung und Herstellung
Methods of Manufacturing
CHLOROETHYLAMINES ARE PREPARED BY ACTION OF THIONYL CHLORIDE ON APPROPRIATE ETHANOLAMINE... FREE BASE IS LIBERATED BY TREATING HYDROCHLORIDE WITH SODIUM HYDROXIDE OR CARBONATE.
RABALD, DIMROTH, GERMAN PATENT 824,208 (1951 TO CF BOEHRINGER, MANN); CA 47, 2206 (1953). /HYDROCHLORIDE/
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