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Home > Encyclopedia > N-(2-Chloroethyl)dibenzylamine

N-(2-Chloroethyl)dibenzylamine

N-(2-Chloroethyl)dibenzylamine structure

N-(2-Chloroethyl)dibenzylamine 

structure
  • CAS No:

    51-50-3

  • Formula:

    C16H18ClN

  • Chemical Name:

    N-(2-Chloroethyl)dibenzylamine

  • Synonyms:

    Benzenemethanamine,N-(2-chloroethyl)-N-(phenylmethyl)-;Dibenzylamine,N-(2-chloroethyl)-;N-(2-Chloroethyl)-N-(phenylmethyl)benzenemethanamine;Dibenamine;Dibenzylchlorethamine;Dibenzylchlorethylamine;N,N-Dibenzyl-β-chloroethylamine;SKF 199;N,N-Dibenzyl-2-chloroethylamine;2-(Dibenzylamino)ethyl chloride;N-(2-Chloroethyl)dibenzylamine;Dibenzyl-2-chloroethylamine;2-(N,N-Dibenzylamino)ethyl chloride

  • Categories:

    Organic Chemistry  >  Amides

Description

An alpha adrenergic antagonist.

N-(2-Chloroethyl)dibenzylamine Basic Attributes

259.777

259.77

43EXU2S56H

DTXSID20199001

OILY LIQUID

2921499090

Characteristics

3.2

3.8

1.0738 (rough estimate)

192 °C

194-195 °C @ Press: 12 Torr

147.3ºC

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/

Safety Information

STABLE IN ACID SOLN BUT RAPIDLY LOSES ACTIVITY IN NEUTRAL OR ALKALINE AQ SOLUTIONS /HYDROCHLORIDE/

Toxicity

...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.

Drug Information

Adrenergic alpha-Antagonists; Sympatholytics|ADRENERGIC BLOCKING AGENTS ARE USEFUL IN PREOPERATIVE MANAGEMENT OF PATIENTS WITH PHEOCHROMOCYTOMA, FOR THEIR PROLONGED TREATMENT IF TUMOR IS MALIGNANT OR OTHERWISE NOT AMENABLE TO SURGERY, & TO PREVENT PAROXYSMAL HYPERTENSION DURING OPERATIVE MANIPULATION OF TUMOR. /ALPHA-ADRENERGIC BLOCKING AGENTS/

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. /HALOALKYLAMINES/|BECAUSE OF DANGER OF SEVERE HYPOTENSION WHEN...ADMIN IN PRESENCE OF HYPOVOLEMIA, IV ADMIN MUST BE SLOW, PT...KEPT UNDER CONSTANT OBSERVATION, & BLOOD OR APPROPRIATE PLASMA-VOL EXPANDER MUST BE ON HAND... INHIBITION OF COMPENSATORY VASOCONSTRICTION...EXAGGERATES DEPRESSOR EFFECTS OF OPIOIDS. /HALOALKYLAMINES/

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. (See all compounds classified as Adrenergic alpha-Antagonists.)|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. (See all compounds classified as Sympatholytics.)

ABSORPTION FROM GI TRACT IS INCOMPLETE & SOMEWHAT CAPRICIOUS... THE METABOLIC FATE OF THESE HIGHLY UNSTABLE AGENTS IS POORLY UNDERSTOOD. /HALOALKYLAMINE ADRENERGIC BLOCKING AGENTS/

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...

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/

Chlorethylamine, Dibenzyl

N-(2-Chloroethyl)dibenzylamine Use and Manufacturing

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/

Uses

MEDICATION

C13-NMR SPECTRA OF DIBENAMINE IS PRESENTED.

Computed Properties

Molecular Weight:259.77
XLogP3:3.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:6
Exact Mass:259.1127773
Monoisotopic Mass:259.1127773
Topological Polar Surface Area:3.2
Heavy Atom Count:18
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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