norfenefrine

Names

[ CAS No. ]:
536-21-0

[ Name ]:
norfenefrine

[Synonym ]:
7,8-Dihydro-14-hydroxynormorphinone
noroxymorphone
Esbuphon
3-(2-Amino-1-hydroxyethyl)phenol
1-(m-hydroxyphenyl)-2-aminoethanol
norfenefrine
4-Hydroxydihydronormorphinone
a-(Aminomethyl)-3-hydroxybenzene Methanol
14-Hydroxydihydronormorphinone
3-[(1RS)-2-amino-1-hydroxyethyl]phenol
DL-[2-hydroxy-2-(3-hydroxyphenyl)ethyl]amine
Zondel
(5|A)-4,5-Epoxy-3,14-dihydroxy-morphinan-6-one
Benzenemethanol, α-(aminomethyl)-3-hydroxy-
norphenylephrine
Stagural
a-(Aminomethyl)-m-hydroxybenzyl Alcohol
Novadral
(5alpha)-4,5-Epoxy-3,14-dihydroxymorphinan-6-one
1-(3'-hydroxy-phenyl)-2-amino-ethanol
DL-m-Octopamine
N-noroxymorphone
Norphenephrine

Biological Activity

[Description]:

Norfenefrine is an orally active, endogenously found α-adrenergic agonist and can be used for the research of female stress incontinence[1][2].

[Related Catalog]:

Research Areas >> Endocrinology

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

[Target]

Adrenergic Receptor[2]

[In Vivo]

Norfenefrine (1.25-5.00 mg/kg; s.c.; once) stimulates respiratory tract mucus secretion in mice[1]. Animal Model: Male NMRI mice[1] Dosage: 1.25, 2.50, and 5.00 mg/kg Administration: Subcutaneous injection, once Result: Stimulated intratracheal phenol red secretion.

[References]

[1]. Engler H, et al. Tracheal phenol red secretion, a new method for screening mucosecretolytic compounds. J Pharmacol Methods. 1984 Jun;11(3):151-7.

[2]. Jørgensen L, et al. Acute effect of norfenefrine on the urethral pressure profile in females with genuine stress incontinence. Urol Int. 1991;46(2):176-9.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
360.7±27.0 °C at 760 mmHg

[ Molecular Formula ]:
C₈H₁₁NO₂

[ Molecular Weight ]:
153.178

[ Flash Point ]:
172.0±23.7 °C

[ Exact Mass ]:
153.078979

[ PSA ]:
66.48000

[ LogP ]:
-0.28

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.614

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DN7250000

CHEMICAL NAME :: Benzyl alcohol, alpha-(aminomethyl)-m-hydroxy-

CAS REGISTRY NUMBER :: 536-21-0

BEILSTEIN REFERENCE NO. :: 1211018

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C8-H11-N-O2

MOLECULAR WEIGHT :: 153.20

WISWESSER LINE NOTATION :: Z1YQR CQ

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 :: 390 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,217,1968

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 32 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,217,1968

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 28100 ug/kg

TOXIC EFFECTS :: Endocrine - hyperglycemia Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,60,1968

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17400 ug/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,217,1968

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 263 mg/kg

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

REFERENCE :: RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,295,1970

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 198 mg/kg

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

REFERENCE :: RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,295,1970

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 459 mg/kg

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

REFERENCE :: RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,295,1970

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4900 ug/kg

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

REFERENCE :: RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,295,1970 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 810 mg/kg/90D-C

TOXIC EFFECTS :: Cardiac - other changes Lungs, Thorax, or Respiration - other changes Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,60,1968

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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