Gepefrine

{{Short description|Sympathomimetic drug in the amphetamine family}}

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 447926897

| drug_name = 3-Hydroxyamphetamine

| image = Gepefrine.png

| image_class = skin-invert-image

| width = 225px

| tradename = Pressionorm, Wintonin

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| elimination_half-life =

| excretion =

| index2_label = S-form

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1075-61-2

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 18840-47-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L9JB0763SW

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = V51RRX51VH

| ATC_prefix = C01

| ATC_suffix = CA15

| PubChem = 219105

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB13703

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 2105064

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 189921

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07150

| synonyms = 3-Hydroxyamphetamine; meta-Hydroxyamphetamine; α-Methyl-meta-tyramine; 3-Hydroxy-α-methylphenethylamine

| IUPAC_name = (±)-3-(2-aminopropyl)phenol

| C=9 | H=13 | N=1 | O=1

| SMILES = OC1=CC(C[C@H](C)N)=CC=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WTDGMHYYGNJEKQ-ZETCQYMHSA-N

}}

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.{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA487 | access-date = 24 April 2012 | year = 2000 | publisher = Taylor & Francis US | isbn = 978-3-88763-075-1 | page = 487}}{{cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA127 | access-date = 24 April 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 127}}{{cite journal | vauthors = Jonsson J | title = Identification of metahydroxyamphetamine as a metabolite of amphetamine in the rat | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 18 | issue = 2 | pages = 189–199 | date = October 1977 | pmid = 918344 }}