Gepefrine

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]

3-Hydroxyamphetamine

Clinical data
Trade names	Pressionorm, Wintonin
Other names	3-Hydroxyamphetamine; meta-Hydroxyamphetamine; α-Methyl-meta-tyramine; 3-Hydroxy-α-methylphenethylamine
ATC code	C01CA15 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (±)-3-(2-aminopropyl)phenol
CAS Number	1075-61-2 Y S-form: 18840-47-6 Y
PubChem CID	219105
DrugBank	DB13703 Y
ChemSpider	189921 Y
UNII	L9JB0763SW S-form: V51RRX51VH Y
KEGG	D07150 Y
ChEMBL	ChEMBL2105064 Y
ECHA InfoCard	100.012.779
Chemical and physical data
Formula	C9H13NO
Molar mass	151.209 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC1=CC(C[C@H](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 Y Key:WTDGMHYYGNJEKQ-ZETCQYMHSA-N Y
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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]