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329-65-7

329-65-7 structure
329-65-7 structure
  • Name: DL-Adrenalin
  • Chemical Name: adrenaline
  • CAS Number: 329-65-7
  • Molecular Formula: C9H13NO3
  • Molecular Weight: 183.204
  • Catalog: Chemical reagent Organic reagent Phenols
  • Create Date: 2018-07-08 11:02:38
  • Modify Date: 2024-01-02 08:11:04
  • 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.

Name adrenaline
Synonyms 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
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
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.

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

Section I.Chemical Product and Company Identification
Chemical Name DL-Adrenaline
Portland OR
SynonymDL-Epinephrine
Chemical FormulaC9H13NO3
CAS Number329-65-7

Section II.Composition and Information on Ingredients
Toxicology Data
Chemical NameCAS Number Percent (%)TLV/PEL
DL-Adrenaline329-65-7Min. 98.0 (T) Not available.Rat LD50 (intravenous) 0.07 mg/kg
Mouse LD50 (intraperitoneal) 7.8
mg/kg
Mouse LD50 (intravenous) 3.4
mg/kg

Section III. Hazards Identification
Acute Health EffectsToxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health EffectsCARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or
many human organs.

Section IV.First Aid Measures
Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
Eye Contact
minutes. Get medical attention.
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing
Skin Contact
and shoes. Wash clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
IngestionINDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

Section V.Fire and Explosion Data
Not available.
May be combustible at high temperature.Auto-Ignition
Flammability
Flash PointsFlammable LimitsNot available.
Not available.
Combustion ProductsThese products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
and Instructions
Continued on Next Page
DL-Adrenaline
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.

Section VI.Accidental Release Measures
Spill CleanupToxic material. Teratogenic material. Irritating material. Light sensitive material. Heat sensitive material.
Stop leak if without risk. DO NOT get water inside container. DO NOT touch spilled material. Use water spray to reduce
Instructions
vapors. Prevent entry into sewers, basements or confined areas; dike if needed. Eliminate all sources of ignition. Consult
federal, state, and/or local authorities for assistance on disposal.

Section VII. Handling and Storage
TOXIC. TERATOGEN. IRRITANT. LIGHT SENSITIVE. HEAT SENSITIVE. REFRIGERATE. Keep locked up. Keep away
Handling and Storage
from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool place. Avoid
Information
excessive heat and light. DO NOT ingest. Do not breathe dust. Wear suitable protective clothing. If ingested, seek medical
advice immediately and show the container or the label. Treat symptomatically and supportively.
Always store away from incompatible compounds such as oxidizing agents, acids.

Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
Personal Protection
inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this
product.
Exposure LimitsNot available.

Section IX. Physical and Chemical Properties
Solid. (Crystal, powder. Pale yellow -Solubility
Physical state @ 20°CNot available.
greyish yellow red.)
Not available.
Specific Gravity
Molecular Weight183.20Partition CoefficientNot available.
Boiling PointNot available.Not applicable.
Vapor Pressure
Melting Point197°C (386.6°F)Vapor DensityNot available.
Not available.Not available.
Refractive IndexVolatility
Critical TemperatureNot available.OdorNot available.
Not available.Not available.
ViscosityTaste

Section X.Stability and Reactivity Data

This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of InstabilityAvoid excessive heat and light.
IncompatibilitiesReactive with oxidizing agents, acids, acid chlorides, acid anhydrides.

Section XI. Toxicological Information
RTECS NumberDO2975000
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Rat LD50 (intravenous) 0.07 mg/kg
Toxicity Data
Mouse LD50 (intraperitoneal) 7.8 mg/kg
Mouse LD50 (intravenous) 3.4 mg/kg
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or many
human organs.
Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Acute Toxic Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Continued on Next Page
DL-Adrenaline

Section XII.Ecological Information
EcotoxicityNot available.
Not available.
Environmental Fate

Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

Section XIV. Transport Information
DOT ClassificationDOT CLASS 6.1: Toxic material.
PIN Number
Proper Shipping NameToxic solid, organic, n.o.s.
II
Packing Group (PG)
DOT Pictograms

Section XV. Other Regulatory Information and Pictograms
TSCA Chemical InventoryThis product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS ClassificationCLASS D-1B: Material causing immediate and serious toxic effects (TOXIC).
On DSL.
(Canada)
EINECS Number (EEC) 206-347-6
EEC Risk StatementsR23/24/25- Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38- Irritating to eyes, respiratory system and skin.


SECTION 16 - ADDITIONAL INFORMATION
N/A

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)
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

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Literature: Annali di Chimica (Rome, Italy), , vol. 41, p. 711,713 Zhurnal Obshchei Khimii, , vol. 28, p. 2530,2536 J. Gen. Chem. USSR (Engl. Transl.), , vol. 28, p. 2566,2570

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Literature: Tetrahedron, , vol. 47, # 27 p. 5019 - 5024

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Literature: Organic and Biomolecular Chemistry, , vol. 6, # 24 p. 4609 - 4614

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Literature: Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie, , vol. 193, p. 440,445 Pr.Soc.exp.Biol.Med., , vol. 45, p. 52
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%