phaclofen

{{Short description|GABAB receptor antagonist}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 449584465

| ImageFile=Phaclofen.svg

| ImageSize=

| IUPACName=[3-amino-2-(4-chlorophenyl)propyl]phosphonic acid

| OtherNames=

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=108351-35-5

| PubChem=1641

| IUPHAR_ligand = 1091

| SMILES=C1=CC(=CC=C1C(CN)CP(=O)(O)O)Cl

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 1579

| InChI = 1/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)

| InChIKey = VSGNGLJPOGUDON-UHFFFAOYAO

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VSGNGLJPOGUDON-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula=C₉H₁₃ClNO₃P

| MolarMass=249.631 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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|Section3={{Chembox Hazards

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Phaclofen, or phosphonobaclofen, is a selective antagonist for the GABA_B receptor.{{cite journal |title = Phaclofen: a peripheral and central baclofen antagonist |vauthors = Kerrn D, Ong J, Prager R, Gynther B, Curtis D |journal = Brain Research |volume = 405 |date = 3 March 1987 |issue = 1 |pages = 150–154 |doi=10.1016/0006-8993(87)90999-1|pmid = 3032346 |s2cid = 29595421 }} It was the first selective GABA_B antagonist discovered, but its utility was limited by the fact that it does not cross the blood brain barrier.{{cite journal |journal=J Med Chem |title=Phosphinic acid analogues of GABA. 2. Selective, orally active GABAB antagonists |pmid=7650685 |date=August 18, 1995 |doi=10.1021/jm00017a016 |vauthors=Froestl W, Mickel SJ, von Sprecher G, Diel PJ, Hall RG, Maier L, Strub D, Melillo V, Baumann PA, Bernasconi R, et. al. |volume=38 |issue=17 |pages=3313–3331 }}