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Home > Encyclopedia > (±)-Adrenaline

(±)-Adrenaline

(±)-Adrenaline structure

(±)-Adrenaline 

structure
  • CAS No:

    329-65-7

  • Formula:

    C9H13NO3

  • Chemical Name:

    (±)-Adrenaline

  • Synonyms:

    1,2-Benzenediol,4-[1-hydroxy-2-(methylamino)ethyl]-;Benzyl alcohol,3,4-dihydroxy-α-[(methylamino)methyl]-,(±)-;1,2-Benzenediol,4-[1-hydroxy-2-(methylamino)ethyl]-,(±)-;4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol;Epirenamine;(±)-Adrenaline;dl-Epinephrine;(±)-Epinephrine;dl-Adrenaline;DL-Adrenaline;Racepinefrine;2-(Methylamino)-1-(3,4-dihydroxyphenyl)ethanol;1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol;Racepinephrine;2-Hydroxy-4-[1-hydroxy-2-(methylazaniumyl)ethyl]phenolate;6912-68-1;8059-19-6;8060-13-7

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

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.


3,4-dihydroxyl-alpha-[methylamino]methylbenzyl alcohol appears as odorless light brown or nearly white crystals. (NTP, 1992)


3,4-dihydroxyl-alpha-[methylamino]methylbenzyl alcohol appears as odorless light brown or nearly white crystals. (NTP, 1992)|Adrenaline is a catecholamine in which the aminoethyl side-chain is hydroxy-substituted at C-1 and methylated on nitrogen. It has a role as a human metabolite.|A racemic mixture of d-epinephrine and l-epinephrine.

(±)-Adrenaline Basic Attributes

183.204

183.20

206-347-6

2811

C10AX10|C - Cardiovascular system

2922509090

Characteristics

72.72000

-0.63

3,4-dihydroxyl-alpha-[methylamino]methylbenzyl alcohol appears as odorless light brown or nearly white crystals. (NTP, 1992)

1.3±0.1 g/cm3

212 °C

413.1±40.0 °C at 760 mmHg

207.9±17.9 °C

1.608

Sparingly soluble

Preserve in tight, light-resistant containers.

7.37X10-8 mm Hg at 25 deg C (est)

Slightly water soluble (NTP, 1992).

Amines, Phosphines, and Pyridines

Light sensitive. Incompatible with heat, air, iron salts, and alkalis. (NTP, 1992). An organic compound with both amine and alcohol substituents. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Incompatible with heat, air, iron salts, and alkalis. (NTP, 1992).

Safety Information

III

6.1(b)

UN 2811 6.1/PG 2

3

R24;R36/37/38

S26-S36/37-S45

DO2975000

T:Toxic;

In some commercially available injections, the air has been replaced with nitrogen to avoid oxidation. Withdrawal of doses from multiple-dose vials introduces air into the vials, subjecting the remaining epinephrine to oxidation. Oxidation of the drug imparts first a pink, then a brown color; epinephrine preparations must not be used if they have a pinkish or darker than slightly yellow color or contain a precipitate.

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

H311

Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide, foam, or Halon extiguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with 5% acetic acid, then transfer the dampened material to a suitable container. Use absorbent paper dampened with 5% acetic acid to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with 5% acetic acid followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to air and light, and store it under freezer conditions. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Drug Information

Glybera is indicated for adult patients diagnosed with familial lipoprotein lipase deficiency (LPLD) and suffering from severe or multiple pancreatitis attacks despite dietary fat restrictions. The diagnosis of LPLD has to be confirmed by genetic testing. The indication is restricted to patients with detectable levels of LPL protein.|Treatment of hyperchylomicronaemia

Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)|Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)|Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)|Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)|Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)|Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)

SYMPTOMS: Pallor, tremor, anxiety, nervousness, rapid, forceful pulse, rise in blood pressure and temperature, rapid breathing, dilation of the pupils. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Adrenaline Hydrochloride, Racemic Mixture

(±)-Adrenaline Use and Manufacturing

Uses

Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma. DL-Adrenaline is a hormone and a neurotransmitter secreted by the medulla of the adrenal glands. In medicine DL-Adrenaline is used chiefly as a stimulant in cardiac arrest, as a vasoconstrictor in shock, and as a bronchodilator and antispasmodic in bronch

Human drugs -> Glybera -> EMA Drug Category|Lipid modifying agents -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:183.20
XLogP3:-1.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:183.08954328
Monoisotopic Mass:183.08954328
Topological Polar Surface Area:72.7
Heavy Atom Count:13
Complexity:154
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Racepinephrine is a sympathomimetic amine used as a bronchodilator to treat conditions such as asthma and other respiratory diseases by stimulating alpha and beta-adrenergic receptors, leading to decreased mucosal edema and improved airflow.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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