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phenyltoloxamine

Names

[ CAS No. ]:
92-12-6

[ Name ]:
phenyltoloxamine

[Synonym ]:
Feniltolossamina [DCIT]
Phenyltoloxamine
Phenoxadrine
Antin
[2-(2-benzyl-phenoxy)-ethyl]-dimethyl-amine
Histionex
2-Dimethylamino-1-(2-benzyl-phenoxy)-aethan
Bistrimin
Phenoxadrin
UNII-K65LB6598J
Phenyl-toloxamin
Phentoloxamine
Bristamin
[2-(2-Benzyl-phenoxy)-aethyl]-dimethyl-amin

Biological Activity

[Description]:

Phenyltoloxamine (Bistrimin) is an antihistamine agent with sedative and analgesic effects. Phenyltoloxamine also has potent Sigma-1 receptor binding affinity (Ki: 160 nM)[1][2][3].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor
Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease
Signaling Pathways >> GPCR/G Protein >> Sigma Receptor
Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

Sigma 1 Receptor:160 nM (Ki)


[In Vitro]

Phenyltoloxamine (10-50 μM, 24 h) demonstrates cytotoxicity in EVSA-T cells[2]. Phenyltoloxamine exhibits potent Sigma 1 Receptor (S1R) binding affinity with a Ki value of 160 nM[3]. Phenyltoloxamine (100 μM) inhibits human liver macrosaml CYP2D6 enzyme by 99.0%[4].

Chemical & Physical Properties

[ Density]:
1.022g/cm3

[ Boiling Point ]:
359.2ºC at 760 mmHg

[ Molecular Formula ]:
C17H21NO

[ Molecular Weight ]:
255.35500

[ Flash Point ]:
106ºC

[ Exact Mass ]:
255.16200

[ PSA ]:
12.47000

[ LogP ]:
3.21780

[ Index of Refraction ]:
1.552

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KH2376000
CHEMICAL NAME :
Ethanamine, N,N-dimethyl-2-(2-(phenylmethyl)phenoxy)-
CAS REGISTRY NUMBER :
92-12-6
BEILSTEIN REFERENCE NO. :
1986598
LAST UPDATED :
199701
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C17-H21-N-O
MOLECULAR WEIGHT :
255.39

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1127 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
246 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
55 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83250 No. of Facilities: 19 (estimated) No. of Industries: 1 No. of Occupations: 9 No. of Employees: 934 (estimated) No. of Female Employees: 506 (estimated)

Synthetic Route

Precursor & DownStream


Related Compounds