Gepefrine

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
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−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 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.[1][2][3][4]

Pharmacology

Gepefrine is described as a sympathomimetic and antihypotensive agent.[5]

Chemistry

Gepefrine, also known as 3-hydroxy-α-methylphenethylamine or as 3-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.[5] It is used pharmaceutically as the (S)-enantiomer and as the tartrate salt.[5][1] 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[5] and was introduced for medical use in Germany by 1981.[3]

Society and culture

Names

Gepefrine is the generic name of the drug and its INNTooltip International Nonproprietary Name.[5] Brand names of gepefrine include Pressionorm and Wintonin.[1][6]

Other drugs

Gepefrine is a known metabolite of amphetamine in rats.[4]

References

  1. ^ a b c 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. ^ a b 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. ^ a b 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. ^ a b c d e 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.