Epinephrine
From DrugPedia: A Wikipedia for Drug discovery
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'''Epinephrine''' (also referred to as '''adrenaline'''; ''see [[#Terminology|Terminology]]'') is a [[hormone]] and [[neurotransmitter]]. It is a [[catecholamine]], a [[sympathomimetic]] [[monoamine]] derived from the [[amino acid]]s [[phenylalanine]] and [[tyrosine]]. The [[Latin]] roots ''ad-''+''renes'' and the [[Greek language|Greek]] roots ''epi-''+''nephros'' both literally mean "on/to the [[kidney]]" (referring to the [[adrenal gland]], which sits atop the kidneys and secretes epinephrine). Epinephrine is often shortened to '''E''' or to '''EPI''' in Medical [[jargon]]. Epinephrine increases the response of the sympathetic division of the Autonomic Nervous System. | '''Epinephrine''' (also referred to as '''adrenaline'''; ''see [[#Terminology|Terminology]]'') is a [[hormone]] and [[neurotransmitter]]. It is a [[catecholamine]], a [[sympathomimetic]] [[monoamine]] derived from the [[amino acid]]s [[phenylalanine]] and [[tyrosine]]. The [[Latin]] roots ''ad-''+''renes'' and the [[Greek language|Greek]] roots ''epi-''+''nephros'' both literally mean "on/to the [[kidney]]" (referring to the [[adrenal gland]], which sits atop the kidneys and secretes epinephrine). Epinephrine is often shortened to '''E''' or to '''EPI''' in Medical [[jargon]]. Epinephrine increases the response of the sympathetic division of the Autonomic Nervous System. | ||
| + | ==History== | ||
| + | Epinephrine was isolated and identified in 1895 by [[Napoleon Cybulski]], a [[Poland|Polish]] [[physiology|physiologist]]. In May 1896, [[William Horatio Bates|William Bates]] reported the discovery of a substance produced by the adrenal gland in the ''New York Medical Journal''.<ref name="bates-eye">{{cite web |url=http://www.central-fixation.com/bates-medical-articles/use-of-extract-of-suprarenal-capsule.php |title=The Use of Extract of Suprarenal Capsule in the Eye - www.Central-Fixation.com |format= |work= |accessdate=}}</ref> The discovery was repeated in 1897 by [[John Jacob Abel]].<ref>Aronson JK (2000). "[http://bmj.bmjjournals.com/cgi/content/full/320/7233/506 Where name and image meet]" - the argument for "adrenaline". ''British Medical Journal'' '''320''', 506-9.</ref> | ||
| + | [[Jokichi Takamine]], a Japanese chemist, independently discovered the same hormone in 1900.<ref>{{cite journal |author=Yamashima T |title=Jokichi Takamine (1854–1922), the samurai chemist, and his work on adrenalin |journal=J Med Biogr |volume=11 |issue=2 |pages=95–102 |year=2003 |pmid=12717538}}</ref><ref>{{cite journal |author=Bennett M |title=One hundred years of adrenaline: the discovery of autoreceptors |journal=Clin Auton Res |volume=9 |issue=3 |pages=145–59 |year=1999 |pmid=10454061 |doi=10.1007/BF02281628}}</ref> In 1901 he isolated and purified the hormone epinephrine from cow glands. | ||
| + | |||
| + | Epinephrine was first artificially synthesized in 1904 by [[Friedrich Stolz]]. | ||
'''KEGG Pathway'''(C00788,D00095) | '''KEGG Pathway'''(C00788,D00095) | ||
*Tyrosine metabolism | *Tyrosine metabolism | ||
Revision as of 06:57, 17 February 2009
Epinephrine Pubchem(5816)
The active sympathomimetic hormone from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics.
Epinephrine (also referred to as adrenaline; see Terminology) is a hormone and neurotransmitter. It is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. The Latin roots ad-+renes and the Greek roots epi-+nephros both literally mean "on/to the kidney" (referring to the adrenal gland, which sits atop the kidneys and secretes epinephrine). Epinephrine is often shortened to E or to EPI in Medical jargon. Epinephrine increases the response of the sympathetic division of the Autonomic Nervous System.
History
Epinephrine was isolated and identified in 1895 by Napoleon Cybulski, a Polish physiologist. In May 1896, William Bates reported the discovery of a substance produced by the adrenal gland in the New York Medical Journal.<ref name="bates-eye">Template:Cite web</ref> The discovery was repeated in 1897 by John Jacob Abel.<ref>Aronson JK (2000). "Where name and image meet" - the argument for "adrenaline". British Medical Journal 320, 506-9.</ref>
Jokichi Takamine, a Japanese chemist, independently discovered the same hormone in 1900.<ref>Yamashima T (2003). "Jokichi Takamine (1854–1922), the samurai chemist, and his work on adrenalin". J Med Biogr 11 (2): 95–102. PMID 12717538.</ref><ref>Bennett M (1999). "One hundred years of adrenaline: the discovery of autoreceptors". Clin Auton Res 9 (3): 145–59. doi:. PMID 10454061.</ref> In 1901 he isolated and purified the hormone epinephrine from cow glands.
Epinephrine was first artificially synthesized in 1904 by Friedrich Stolz. KEGG Pathway(C00788,D00095)
- Tyrosine metabolism
- Neuroactive ligand-receptor interaction
Target
- alpha1a-adrenergic receptor agonist
- alpha1b-adrenergic receptor agonist
- alpha1d-adrenergic receptor agonist
- alpha2a-adrenergic receptor agonist
- alpha2b-adrenergic receptor agonist
- alpha2c-adrenergic receptor agonist
- beta1-adrenergic receptor agonist
- beta2-adrenergic receptor agonist
- beta3-adrenergic receptor agonist
Activity Adrenergic [vasoconstrictor]
| Physical Property | Value | Units | Temp (deg C) | Source |
|---|---|---|---|---|
| Melting Point | 211.5 | deg C | EXP | |
| pKa Dissociation Constant | 8.59 | (none) | 25 | EXP |
| log P (octanol-water) | (-1.37E+00) | (none) | EXP | |
| Water Solubility | 180 | mg/L | 20 | EXP |
| Vapor Pressure | 7.37E-07 | mm Hg | 25 | EST |
| Henry's Law Constant | 7.06E-19 | atm-m3/mole | 25 | EST |
| Atmospheric OH Rate Constant | 1.38E-10 | cm3/molecule-sec | 25 | EST |
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | intravenous | 500ug/kg (0.5mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| cat | LDLo | subcutaneous | 20mg/kg (20mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| dog | LD50 | intravenous | 100ug/kg (0.1mg/kg) | Drugs in Japan Vol. 6, Pg. 120, 1982. | |
| dog | LD50 | subcutaneous | 5mg/kg (5mg/kg) | Drugs in Japan Vol. 6, Pg. 120, 1982. | |
| dog | LDLo | parenteral | 5ug/kg (0.005mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 1, Pg. 189, 1968. |
| guinea pig | LDLo | intravenous | 100ug/kg (0.1mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| guinea pig | LDLo | subcutaneous | 800ug/kg (0.8mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| infant | TDLo | multiple routes | 625ug/kg/I (0.625mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
LUNGS, THORAX, OR RESPIRATION: CYANOSIS KIDNEY, URETER, AND BLADDER | "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Southern Medical Journal. Vol. 78, Pg. 874, 1985. |
| man | LDLo | subcutaneous | 7ug/kg (0.007mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
CARDIAC: OTHER CHANGES | Annals of Emergency Medicine. Vol. 28, Pg. 725, 1996. |
| man | TDLo | intramuscular | 2ug/kg (0.002mg/kg) | VASCULAR: REGIONAL OR GENERAL ARTERIOLAR CONSTRICTION | American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990. |
| man | TDLo | intravenous | 16ug/kg (0.016mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | American Journal of Emergency Medicine. Vol. 5, Pg. 64, 1987. |
| man | TDLo | intravenous | 285ug/kg (0.285mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | American Journal of Emergency Medicine. Vol. 7, Pg. 485, 1989. |
| man | TDLo | intravenous | 3mg/kg (3mg/kg) | VASCULAR: CONTRACTION (ISOLATED TISSUES) | American Journal of Emergency Medicine. Vol. 8, Pg. 46, 1990. |
| man | TDLo | oral | 77mg/kg (77mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: NAUSEA OR VOMITING | Annals of Emergency Medicine. Vol. 19, Pg. 671, 1990. |
| man | TDLo | subcutaneous | 8571ng/kg/80M (0.008571mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION | American Heart Journal. Vol. 111, Pg. 1193, 1986. |
| man | TDLo | subcutaneous | 43ug/kg (0.043mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Annals of Emergency Medicine. Vol. 19, Pg. 680, 1990. |
| mouse | LD50 | intraperitoneal | 4mg/kg (4mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 110, 1947. | |
| mouse | LD50 | intravenous | 217ug/kg (0.217mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976. |
| mouse | LD50 | subcutaneous | 1470ug/kg (1.47mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 202, Pg. 658, 1943. | |
| mouse | LDLo | oral | 50mg/kg (50mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| mouse | LDLo | unreported | 10mg/kg (10mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: EXCITEMENT | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 162, Pg. 46, 1931. |
| rabbit | LD50 | intravenous | 50ug/kg (0.05mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rabbit | LD50 | subcutaneous | 4mg/kg (4mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rabbit | LDLo | oral | 30mg/kg (30mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| rat | LD50 | intramuscular | 3500mg/kg (3500mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 105, 1973. | |
| rat | LD50 | intravenous | 150ug/kg (0.15mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 41, Pg. 365, 1931. | |
| rat | LD50 | skin | 62mg/kg (62mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(4), Pg. 30, 1964. |
| rat | LD50 | subcutaneous | 5mg/kg (5mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941. |
| rat | LDLo | intraperitoneal | 10mg/kg (10mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 268, 1946. |
| rat | LDLo | oral | 30mg/kg (30mg/kg) | "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 22, 1948. | |
| women | TDLo | intravenous | 6ug/kg (0.006mg/kg) | CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | British Medical Journal. Vol. 286, Pg. 519, 1983. |
