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 ; S-form: 18840-47-6 ;
PubChem CID	219105;
DrugBank	DB13703 ;
ChemSpider	189921 ;
UNII	L9JB0763SW; S-form: V51RRX51VH ;
KEGG	D07150 ;
ChEMBL	ChEMBL2105064 ;
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 ; 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.^[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

^ ^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.
^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 127. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
^ ^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.
^ ^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.
^ ^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.
^ Challener, C.A. (2017). Chiral Drugs. Routledge Revivals. Taylor & Francis. p. 552. ISBN 978-1-351-80804-0. Retrieved 1 September 2024.

[IndexNominum2000-1] 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 (1997). Dictionary of Pharmacological Agents. CRC Press. p. 127. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.

[PharmManuEnc2013-3] 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.

[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.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine