racepinefrine

{{Short description|Chemical compound}}

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{{Infobox drug

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| image = Adrenaline.svg

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| tradename = AsthmaNefrin, Dey-Dose, Micronefrin, Nephron, S-2 Inhalant, Vaponefrin, Vaponephrin

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| CAS_number = 329-65-7

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| PubChem = 838

| IUPHAR_ligand =

| DrugBank = DB11124

| ChemSpiderID = 815

| UNII = GR0L9S3J0F

| KEGG = D05688

| ChEBI = 194548

| ChEMBL = 1740

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| synonyms = Racepinephrine; Racemic epinephrine; Racemic adrenaline; DL-Epinephrine; DL-Adrenaline; dl-Epinephrine; dl-Adrenaline; (±)-Epinephrine; (±)-Adrenaline

| IUPAC_name = 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

| C=9 | H=13 | N=1 | O=3

| SMILES = CNCC(C1=CC(=C(C=C1)O)O)O

| StdInChI = 1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3

| StdInChIKey = UCTWMZQNUQWSLP-UHFFFAOYSA-N

}}

Racepinefrine ({{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|USAN|United States Adopted Name}}), or racepinephrine, sold under the brand name Vaponefrin among others, is a sympathomimetic medication described as a vasoconstrictor, bronchodilator, cardiostimulant, mydriatic, and antiglaucoma agent.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA247 | access-date=1 September 2024 | page=1-PA247}}{{cite book | vauthors = Buckingham J | title=Dictionary of Natural Products | publisher=Taylor & Francis | year=1993 | isbn=978-0-412-46620-5 | url=https://books.google.com/books?id=1W0NUD42fA4C&pg=PA87 | access-date=2024-09-01 | page=87}}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | series=Index nominum | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA909 | access-date=1 September 2024 | page=909}}{{cite book | author = W.A.W.A. Publishing | title=Pharmaceutical Manufacturing Encyclopedia | publisher=Elsevier Science | series=Volumes 1-4 | year=2013 | isbn=978-0-8155-1856-3 | url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1448 | access-date=1 September 2024 | pages=1448–1449}}{{cite book | vauthors = Milne GW | title=Drugs: Synonyms and Properties | publisher=Taylor & Francis | series=Routledge Revivals | year=2018 | isbn=978-1-351-78990-5 | url=https://books.google.com/books?id=dloPEAAAQBAJ&pg=PA513 | access-date=1 September 2024 | page=513}} It is the racemic form of epinephrine (adrenaline) and is also known as dl-epinephrine and (±)-epinephrine. The drug is used pharmaceutically as the hydrochloride salt. It has been marketed in the United States and Canada.