N-(2-Chloroethyl)dibenzylamine

HCID 5820

Basic information

CAS
51-50-3
Standard SMILES
ClCCN(Cc1ccccc1)Cc1ccccc1
InChIKey
GSLWSSUWNCJILM-UHFFFAOYSA-N
Molecular formula
C16H18ClN
Average molar mass
259.77 g/mol
Monoisotopic mass
259.11277726

Names & identifiers

Preferred name
N-(2-Chloroethyl)dibenzylamine
IUPAC
N,N-dibenzyl-2-chloroethanamine
English name
Dibenamine
Molecular formula
C16H18ClN
Molecular weight
259.77

Names & synonyms

DIBENAMINE51-50-3N-(2-Chloroethyl)dibenzylamineN,N-Dibenzyl-2-chloroethanamine2-(Dibenzylamino)ethyl chlorideDibenzylchlorethylamine2-ChloroethyldibenzylamineSKF 199Dibenzylamine, N-(2-chloroethyl)-N,N-Dibenzyl-2-chloroethylamineN,N-Dibenzyl-beta-chloroethylamine43EXU2S56H
Show more names
N,N-Dibenzyl-2-chloroethan-1-amine(2-Chloroethyl)dibenzylaminebis(benzyl)-(2-chloroethyl)amine2-chloro-N,N-bis(phenylmethyl)ethanamine
DTXSID20199001Benzenemethanamine, N-(2-chloroethyl)-N-(phenylmethyl)-RefChem:388925DTXCID10121492DibenzylchlorethamineDibenzyl chlorethylamineDibenzyl(2-chloroethyl)amineN,N-Dibenzyl-.beta.-chloroethylamine

Database identifiers

CAS
51-50-3
PubChem CID
5820
DTXSID
DTXSID20199001
ChEMBL
CHEMBL3305685
UNII
43EXU2S56H
Nikkaji
J10.688G

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
3.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
18

Experimental & physicochemical properties

Color/FormOILY LIQUID
Stability/Shelf Life · 2 items

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 · 2 items

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/

Physicochemical properties

Melting point
192 °C · 192 °C
Boiling point
407.11 °C · 407.11°C (rough estimate)
Density
1.0738 · 1.0738 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
pka
6.5 · 6.50±0.50(Predicted)
FDA UNII
43 EXU2S56H · 43EXU2S56H

Safety & regulation

Toxicology

Interactions · 5 items

...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 · 3 items

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 · 2 items

...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.

Safety data

Hazardous Substances Data
51-50-3(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

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 · 2 items

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.

Absorption, Distribution and ExcretionABSORPTION FROM GI TRACT IS INCOMPLETE & SOMEWHAT CAPRICIOUS... THE METABOLIC FATE OF THESE HIGHLY UNSTABLE AGENTS IS POORLY UNDERSTOOD. /HALOALKYLAMINE ADRENERGIC BLOCKING AGENTS/

Uses & manufacturing

UsesMEDICATION
Methods of Manufacturing · 2 items

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/

Applications

UsesDibenamine is an alpha-adrenergic antagonist that exhibits the ability to block both basal and histamine-stimulated gastric acid secretion, making it therapeutically relevant in conditions involving excessive gastric acid production.

Suppliers3 total

上海之坤生物科技有限公司15821335126 15821335126 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

Related reactions

12 records

Compound notes

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