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Gepefrine

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(Redirected from 3-Hydroxyamphetamine) 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
IUPAC name
  • (±)-3-(2-aminopropyl)phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.012.779 Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol
3D model (JSmol)
SMILES
  • OC1=CC(C(C)N)=CC=C1
InChI
  • 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
  • Key:WTDGMHYYGNJEKQ-ZETCQYMHSA-N
  (verify)

Gepefrine, also known as 3-hydroxyamphetamine or α-methyl-meta-tyramine and sold under the brand names Pressionorm and Wintonin, is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany.

Pharmacology

Gepefrine is described as a sympathomimetic and antihypotensive agent.

Chemistry

Gepefrine, also known as 3-hydroxy-α-methylphenethylamine or as 3-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. It is used pharmaceutically as the (S)-enantiomer and as the tartrate salt. Related compounds include meta-tyramine (3-hydroxyphenethylamine), 4-hydroxyamphetamine (norpholedrine), 3,4-dihydroxyamphetamine (α-methyldopamine), and metaraminol ((1R,2S)-3,β-dihydroxyamphetamine), among others.

History

Gepefrine was synthesized by 1968 and was introduced for medical use in Germany by 1981.

Society and culture

Names

Gepefrine is the generic name of the drug and its INNTooltip International Nonproprietary Name. Brand names of gepefrine include Pressionorm and Wintonin.

Other drugs

Gepefrine is a known metabolite of amphetamine in rats.

References

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 487. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.
  2. Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 127. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
  3. ^ Publishing, W.A.W.A. (2013). Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. Elsevier Science. p. 1760. ISBN 978-0-8155-1856-3. Retrieved 2024-09-01.
  4. ^ Jonsson 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. ^ Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. pp. 73–74. ISBN 978-1-4757-2085-3. Retrieved 2024-09-01.
  6. Challener, C.A. (2017). Chiral Drugs. Routledge Revivals. Taylor & Francis. p. 552. ISBN 978-1-351-80804-0. Retrieved 1 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
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulatorsMonoamine reuptake inhibitorsAdrenergicsDopaminergicsSerotonergicsMonoamine metabolism modulatorsMonoamine neurotoxins
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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