Gepefrine

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;
	(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.¹²³⁴

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.⁵¹ 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 1968⁵ 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.¹⁶

Other drugs

Gepefrine is a known metabolite of amphetamine in rats.⁴

References

"Gepefrine (Rec.INN)". Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 487. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.
Macdonald, F, ed. (1997). "Gepefrine". Dictionary of Pharmacological Agents. CRC Press. p. 127. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
"Gepefrin". Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. William Andrew Pub. 2013. p. 1760. ISBN 978-0-8155-1856-3. Retrieved 2026-05-21 – via Google Books.
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.
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.
Challener, C.A. (2017). Chiral Drugs. Routledge Revivals. Taylor & Francis. p. 552. ISBN 978-1-351-80804-0. Retrieved 1 September 2024 – via Google Books.

[IndexNominum2000-1] "Gepefrine (Rec.INN)". Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 487. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.

[Macdonald1997-2] Macdonald, F, ed. (1997). "Gepefrine". Dictionary of Pharmacological Agents. CRC Press. p. 127. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.

[PharmManuEnc2013-3] "Gepefrin". Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. William Andrew Pub. 2013. p. 1760. ISBN 978-0-8155-1856-3. Retrieved 2026-05-21 – via Google Books.

[Jonsson1977-4] 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.

[Elks2014-5] 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.

[Challener2017-6] Challener, C.A. (2017). Chiral Drugs. Routledge Revivals. Taylor & Francis. p. 552. ISBN 978-1-351-80804-0. Retrieved 1 September 2024 – via Google Books.

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