Adiphenine Hydrochloride

Names

[ CAS No. ]:
50-42-0

[ Name ]:
Adiphenine Hydrochloride

[Synonym ]:
Trasentin Hydrochloride
MFCD00242658
Benzeneacetic acid, α-phenyl-, 2-(diethylamino)ethyl ester, hydrochloride (1:1)
2-Diethylaminoethyl diphenylacetate hydrochloride
Adiphenine HCl
Benzeneacetic acid, α-phenyl-, 2- (diethylamino)ethyl ester, hydrochloride
Trasentine
Diphenylacetic Acid 2-(Diethylamino)ethyl Ester Hydrochloride
EINECS 200-036-9
2-(Diethylamino)ethyl diphenylacetate hydrochloride (1:1)
Lunal
Diphenylacetyldiethylaminoethanol Hydrochloride
a-Phenylbenzeneacetic Acid 2-(Diethylamino)ethyl Ester Hydrochloride
2-(diethylamino)ethyl 2,2-diphenylacetate,hydrochloride
Acetic acid, diphenyl-, 2- (diethylamino)ethyl ester hydrochloride
Adiphenine Hydrochloride
2-(Diethylamino)ethyl Diphenylacetate Hydrochloride
Adiphenine (hydrochloride)

Biological Activity

[Description]:

Adiphenine HCl is a nicotinic receptor inhibitor, used as an antispasmodic drug.Target: nAChRAdiphenine decreased the frequency of ACh-induced single-channel currents. adiphenine decreased cluster duration (36-fold at 100 micromolxL(-1)). adiphenine did not change amplitude but increased the decay rate (IC(50)= 15 micromolxL(-1)) [1]. Adiphenine was administered in3H-labelled form in doses of 15 u.mole/kg intravenously to male Wistar rats. Plasma and brain levels of the unchanged drug were measured [1]. The elimination of the3H -labelled compound from the plasma was monophasic with a half-life of 13 minutes. The unchanged drug was detectable in the plasma for 30 minutes after the injection. The time course of brain levels of unchanged drug paralleled that found in the plasma with a half-life of 9 to 12 minutes. In all experiments, brain and plasma levels of unchanged adiphenine correlate highly [2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Neurological Disease

[References]

[1]. Spitzmaul, G., et al., The local anaesthetics proadifen and adiphenine inhibit nicotinic receptors by different molecular mechanisms. Br J Pharmacol, 2009. 157(5): p. 804-17.

[2]. Michelot, J., et al., Adiphenine plasma levels and blood-brain barrier crossing in the rat. Eur J Drug Metab Pharmacokinet, 1985. 10(4): p. 273-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
423ºC at 760 mmHg

[ Melting Point ]:
71-74 °C(lit.)

[ Molecular Formula ]:
C₂₀H₂₆ClNO₂

[ Molecular Weight ]:
347.879

[ Flash Point ]:
133.2ºC

[ Exact Mass ]:
347.165222

[ PSA ]:
29.54000

[ LogP ]:
4.50550

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AH2625000

CHEMICAL NAME :: Acetic acid, diphenyl-, 2-(diethylamino)ethyl ester, hydrochloride

CAS REGISTRY NUMBER :: 50-42-0

LAST UPDATED :: 199603

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C20-H25-N-O2.Cl-H

MOLECULAR WEIGHT :: 347.92

WISWESSER LINE NOTATION :: 2N2&2OVYR&R &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 96,151,1949

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 81,174,1944

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 59,149,1938

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 185 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 82,23,1944

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 33,145,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 27 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 96,151,1949

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intradermal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1250 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 59,149,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Cardiac - other changes Lungs, Thorax, or Respiration - other changes

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 59,365,1937

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Cardiac - other changes Lungs, Thorax, or Respiration - other changes

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 59,365,1937

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Cardiac - other changes Lungs, Thorax, or Respiration - other changes

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 59,365,1937

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BDCBAD Berichte der Deutschen Chemischen Gesellschaft. Abteilung B: Abhandlungen. (Heidelberg, Fed. Rep. Ger.) V.62-77, 1929-45. For publisher information, see CHBEAM. Volume(issue)/page/year: 72,1551,1939

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - tremor Lungs, Thorax, or Respiration - other changes

REFERENCE :: QJPPAL Quarterly Journal of Pharmacy & Pharmacology. (London, UK) V.2-21, 1929-48. For publisher information, see JPPMAB. Volume(issue)/page/year: 11,679,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - tremor Lungs, Thorax, or Respiration - other changes

REFERENCE :: QJPPAL Quarterly Journal of Pharmacy & Pharmacology. (London, UK) V.2-21, 1929-48. For publisher information, see JPPMAB. Volume(issue)/page/year: 11,679,1938

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes Cardiac - other changes

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 59,365,1937

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 14,731,1959

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - ataxia Lungs, Thorax, or Respiration - other changes

REFERENCE :: QJPPAL Quarterly Journal of Pharmacy & Pharmacology. (London, UK) V.2-21, 1929-48. For publisher information, see JPPMAB. Volume(issue)/page/year: 11,679,1938

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AH2625000

Related Compounds

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