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DL-Adrenalin

Names

[ CAS No. ]:
329-65-7

[ Name ]:
DL-Adrenalin

[Synonym ]:
EINECS 206-347-6
4-[1-Hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-
dl-Epinephrine
Epinephrine dl-
adrenaline
rac Epinephrine
MFCD00063027
1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
(±)-3,4-Dihydroxy-a-[(methylamino)methyl]benzyl Alcohol
(±)-Epinephrine
Drenamist
UNII:GR0L9S3J0F
(±)-Adrenaline
4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
DL-Adrenalin
Benzyl alcohol, 3,4-dihydroxy-α-((methylamino)methyl)-, (-)-
(±)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
(±)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-
Epinephrin
Racepinephrine
Racemic epinephrine
Asthmanefrin

Biological Activity

[Description]:

DL-Epinephrine is the racemate of epinephrine. L-Epinephrine is a hormone secreted by the medulla of the adrenal glands. L-Epinephrine is an α-adrenergic and β-adrenergic receptor agonist.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Research Areas >> Neurological Disease

[In Vivo]

A 25 microliter volume of a 1-% L-epinephrine borate solution applied on the cornea of one eye in 12 monkeys reduces blood flow through the iris and the ciliary body by 59% and 20%, respectively, compared to the untreated control eyes[1]. Epinephrine is a direct-acting sympathomimetic α-adrenergic and β-adrenergic agonist with cyclic adenosine monophosphate-mediated, complex, bidirectional pharmacologic effects on many target organs[2]. In young adult rats, endogenous release of epinephrine facilitates stable memory formation for temporally associated events. Epinephrine enhances memory in young adult rats, in part, by increasing blood glucose levels needed to modulate memory[3]. Epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest. Epinephrine increases arterial blood pressure and coronary perfusion during CPR via alpha-1-adrenoceptor agonist effects[4].

[Animal admin]

Rats: For the immunohistochemistry experiments, rats receive an immediate post-training subcutaneous injection of saline (0.9%), glucose (250 mg/kg), or epinephrine (0.1 mg/kg) and are then returned to the holding cage[3].

[References]

[1]. Alm A, et al. The effect of topical l-epinephrine on regional ocular blood flow in monkeys. Invest Ophthalmol Vis Sci. 1980 May;19(5):487-91.

[2]. Simons FE, et al. First-aid treatment of anaphylaxis to food: focus on epinephrine. J Allergy Clin Immunol. 2004 May;113(5):837-44.

[3]. Morris KA, et al. Epinephrine and glucose modulate training-related CREB phosphorylation in old rats: relationships to age-related memory impairments. Exp Gerontol. 2013 Feb;48(2):115-27.

[4]. Callaway CW, et al. Epinephrine for cardiac arrest. Curr Opin Cardiol. 2013 Jan;28(1):36-42.


[Related Small Molecules]

Isoprenaline hydrochloride | ICI 118,551 (hydrochloride) | Phenylephrine hydrochloride | Yohimbine hydrochloride | Adrenaline | Ivabradine hydrochloride | Prazosin hydrochloride | Clenbuterol hydrochloride | Phentolamine mesilate | guanfacine hydrochloride | pimozide | Sotalol hydrochloride | Carvedilol | Atenolol | Metroprolol succinate

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
413.1±40.0 °C at 760 mmHg

[ Melting Point ]:
197 °C (dec.)(lit.)

[ Molecular Formula ]:
C9H13NO3

[ Molecular Weight ]:
183.204

[ Flash Point ]:
207.9±17.9 °C

[ Exact Mass ]:
183.089539

[ PSA ]:
72.72000

[ LogP ]:
-0.63

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.608

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Sparingly soluble

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DO2975000
CHEMICAL NAME :
Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (+-)-
CAS REGISTRY NUMBER :
329-65-7
BEILSTEIN REFERENCE NO. :
2212160
LAST UPDATED :
199709
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C9-H13-N-O3
MOLECULAR WEIGHT :
183.23
WISWESSER LINE NOTATION :
QR BQ DYQ1M1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
70 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea
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: 95,502,1949
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 68,501,1948
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,57,1948
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3400 ug/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - other changes Kidney, Ureter, Bladder - inflammation, necrosis, or scarring of bladder
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: 95,502,1949
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
250 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,57,1948 *** REVIEWS *** TOXICOLOGY REVIEW CHREAY Chemical Reviews. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1924- Volume(issue)/page/year: 9,389,1931 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4149 No. of Facilities: 399 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 8846 (estimated) No. of Female Employees: 6257 (estimated)

Safety Information

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R24;R36/37/38

[ Safety Phrases ]:
S26-S36/37-S45

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
DO2975000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2922509090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%


Related Compounds