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Gepefrine

From Wikipedia, the free encyclopedia
Sympathomimetic drug in the amphetamine family
Pharmaceutical compound
3-Hydroxyamphetamine
Clinical data
Trade namesPressionorm, Wintonin
Other names3-Hydroxyamphetamine;meta-Hydroxyamphetamine; α-Methyl-meta-tyramine; 3-Hydroxy-α-methylphenethylamine
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (±)-3-(2-aminopropyl)phenol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.012.779Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)
  • OC1=CC(C[C@H](C)N)=CC=C1
  • InChI=1S/C9H13NO/c1-7(10)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5,10H2,1H3/t7-/m0/s1 checkY
  • Key:WTDGMHYYGNJEKQ-ZETCQYMHSA-N checkY
  (verify)

Gepefrine, also known as3-hydroxyamphetamine orα-methyl-meta-tyramine and sold under the brand namesPressionorm andWintonin, is asympathomimeticmedication used as anantihypotensive agent which has been marketed inGermany.[1][2][3][4]

Pharmacology

[edit]

Gepefrine is described as asympathomimetic andantihypotensive agent.[5]

Chemistry

[edit]

Gepefrine, also known as 3-hydroxy-α-methylphenethylamine or as 3-hydroxyamphetamine, is asubstituted phenethylamine andamphetaminederivative.[5] It is usedpharmaceutically as the (S)-enantiomer and as thetartratesalt.[5][1] Related compounds includemeta-tyramine (3-hydroxyphenethylamine),4-hydroxyamphetamine (norpholedrine),3,4-dihydroxyamphetamine (α-methyldopamine), andmetaraminol ((1R,2S)-3,β-dihydroxyamphetamine), among others.

History

[edit]

Gepefrine wassynthesized by 1968[5] and was introduced for medical use inGermany by 1981.[3]

Society and culture

[edit]

Names

[edit]

Gepefrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name.[5] Brand names of gepefrine includePressionorm andWintonin.[1][6]

Other drugs

[edit]

Gepefrine is a knownmetabolite ofamphetamine in rats.[4]

References

[edit]
  1. ^abcIndex Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 487.ISBN 978-3-88763-075-1. Retrieved24 April 2012.
  2. ^Macdonald F (1997).Dictionary of Pharmacological Agents. CRC Press. p. 127.ISBN 978-0-412-46630-4. Retrieved24 April 2012.
  3. ^abPublishing, W.A.W.A. (2013).Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. Elsevier Science. p. 1760.ISBN 978-0-8155-1856-3. Retrieved2024-09-01.
  4. ^abJonsson J (October 1977). "Identification of metahydroxyamphetamine as a metabolite of amphetamine in the rat".Research Communications in Chemical Pathology and Pharmacology.18 (2):189–199.PMID 918344.
  5. ^abcdeElks, J. (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. pp. 73–74.ISBN 978-1-4757-2085-3. Retrieved2024-09-01.
  6. ^Challener, C.A. (2017).Chiral Drugs. Routledge Revivals. Taylor & Francis. p. 552.ISBN 978-1-351-80804-0. Retrieved1 September 2024.
Cardiac stimulants excluding cardiac glycosides (C01C)
Adrenergic and
dopaminergic agents
Adrenergic agonists
α
β
mixed
Dopamine agonists
Both
Unknown/ungrouped
Phosphodiesterase inhibitors (PDE3I)
Other cardiac stimulants
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
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