Deoxyepinephrine
Names | |
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Preferred IUPAC name
4-[2-(Methylamino)ethyl]benzene-1,2-diol | |
Other names
Epinine; N-Methyldopamine
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Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.007.200 |
KEGG | |
MeSH | Deoxyepinephrine |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H13NO2 | |
Molar mass | 167.21 g/mol |
Appearance | colorless crystalline solid |
Melting point | 188 to 189 °C (370 to 372 °F; 461 to 462 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Deoxyepinephrine, also known by the common names N-methyldopamine and epinine, is an
Occurrence
Epinine does not seem to occur widely, but it is present as a minor alkaloid in some plants, such as the
Chemistry
Preparation
The first total synthesis of epinine was reported by Buck, who prepared it from
An earlier
Common salts of epinine are: hydrochloride, C9H13NO2.HCl, m.p. 179-180 °C; sulfate, (C9H13NO2)2.H2SO4, m.p. 289-290 °C;[1] hydrobromide, C9H13NO2.HBr, m.p. 165-166 °C.[11]
Structure
The X-ray structure of epinine hydrobromide has been reported.[13]
Pharmacology
One of the most prominent pharmacological characteristics of epinine, its ability to raise blood pressure, was noted as early as 1910, by Barger and Dale, who reported that "methylamino-ethyl-catechol", as they called it, had about 1/7 x the
Eventually, epinine was determined to be a non-selective stimulant of dopamine (DA) receptors, α-, and β-
Comparable studies, in which blood pressure, heart rate and serum prolactin levels were measured after the administration of 0.5-4 μg/kg/min of epinine by i.v. infusion over a 15-minute period to healthy humans, were reported subsequently by Daul and co-workers.[17] These investigators found that at lower doses (0.5 or 1.0 μg/kg/min), which produced plasma concentrations of 20-80 nM/L, epinine, in common with dopamine, caused a fall in prolactin level, but did not affect blood pressure or heart rate. At higher doses (2.0 or 4.0 μg/kg/min), epinine significantly increased both systolic and diastolic blood pressure, as well as heart rate. In contrast, dopamine caused an increase in systolic blood pressure and heart rate only. Both drugs increased
Toxicity
LD50 for HCl salt: 212 mg/kg (mouse; i.p.). For comparison, it might be noted that dopamine has a LD50 of 1978 mg/kg under the same conditions.[18]
See also
References
- ^ a b c F. L. Pyman (1910). "XXVIII. Isoquinoline derivatives. Part III. o-Dihydroxy-bases. The conversion of 1-keto-6,7-dimethoxy-2-methyltetrahydroisoquinolines into 3:4-dihydroxyphenylethylalkylamines." J. Chem. Soc., Trans. 97 264-280.
- ^ P. A. Zwieten (1994). "Pharmacotherapy of congestive heart failure." Pharmacy World & Science 16 334 - 342.
- ^ R. Gifford, W. C. Randolph, F. C. Heineman and J. A. Ziemniak (1986). "Analysis of epinine and its metabolites in man after oral administration of its pro-drug ibopamine using high-performance liquid chromatography with electrochemical detection." Journal of Chromatography B 381 83-93. doi 10.1016/S0378-4347(00)83567-7
- ^ J. Lundstrom (1971). "Biosynthesis of mescaline and tetrahydroisoquinoline alkaloids in Lophophora williamsii (Lem.) Coult. Occurrence and biosynthesis of catecholamine and other intermediates." Acta Chem. Scand. 25 3489-3499. http://actachemscand.dk/pdf/acta_vol_25_p3489-3499.pdf
- ^ B. A. Clement, C. M. Goff and T. D. A. Forbes (1998). "Toxic amines and alkaloids from Acacia rigidula." Phytochemistry 49 1377-1380.
- ^ T. A. Smith (1977). "Phenethylamine and related compounds in plants." Phytochemistry 16 9-18.
- ^ P. Laduron, P. van Gompel, J. Leysen and M. Claeys (1974). " In vivo formation of epinine in adrenal medulla. A possible step for adrenaline biosynthesis." Naunyn-Schmiedebergs Arch. Pharmacol. 286 227-238.
- ^ F. Märki, J. Axelrod and B. Witkop (1962). "Catecholamines and N-methyltransferase in the South American toad (Bufo marinus)." Biochim. Biophys. Acta 58 367-369.
- ^ S. Tanaka and N. Takeda (1997). "Biogenic monoamines in the brain and the corpus cardiacum between albino and normal strains of the migratory locust, Locusta migratoria." Comp. Biochem. Physiol. Pt. C: Comp. Pharmacol. Toxicol. 117 221-227.
- ^ a b J. S. Buck (1930). "Synthesis of lodal and epinine." J. Am. Chem. Soc. 52 4119-4122.
- ^ a b R. Borgman et al. (1973). "Synthesis and pharmacology of centrally acting dopamine derivatives and analogs in relation to Parkinson's Disease." J. Med. Chem. 16 630-633.
- ^ The Merck Index, 15th Ed. (2013), p. 524 Monograph 2904, O'Neil: The Royal Society of Chemistry. Available online at: http://www.rsc.org/Merck-Index/monograph/mono1500002904
- ^ J. Giesecke (1976). "The structure of the catecholamines. V. The crystal and molecular structure of epinine hydrobromide." Acta Crystallographica Section B 32 2337-2340.
- ^ G. Barger and H. H. Dale (1910)."Chemical structure and sympathomimetic action of amines." J. Physiol. 41 19-59.
- ^ a b M. L. Tainter (1930). "Comparative actions of sympathomimetic compounds: catechol derivatives." J. Pharmacol. Exp. Ther. 40 43-64.
- ^ L. J. van Woerkens, F. Boomsma, A. J. Man in 't Veld, M. M. Bevers, P. D. Verdouw (1992). "Differential cardiovascular and neuroendocrine effects of epinine and dopamine in conscious pigs before and after adrenoceptor blockade." Br. J. Pharmacol. 107 303–310.
- ^ A. Daul et al. (1995). "Dose-dependent separation of dopaminergic and adrenergic effects of epinine in healthy volunteers." Naunyn-Schmiedebergs Arch. Pharmacol. 352 429-437
- ^ J. Z. Ginos et al. (1975). "Cholinergic effects of molecular segments of apomorphine and dopaminergic effects of N,N-dialkylated dopamines." 18 1194-1200.