SCH-50911 Names Preferred IUPAC name 2-[(2S )-5,5-Dimethylmorpholin-2-yl]acetic acid
Identifiers ChemSpider MeSH SCH-50911 UNII InChI=1S/C8H15NO3/c1-8(2)5-12-6(4-9-8)3-7(10)11/h6,9H,3-5H2,1-2H3,(H,10,11)/t6-/m0/s1
Y Key: SEYCKMQSPUVYEF-LURJTMIESA-N
Y InChI=1/C8H15NO3/c1-8(2)5-12-6(4-9-8)3-7(10)11/h6,9H,3-5H2,1-2H3,(H,10,11)/t6-/m0/s1
Key: SEYCKMQSPUVYEF-LURJTMIEBV
O=C(O)C[C@@H]1OCC(NC1)(C)C
Properties C8 H15 NO3 Molar mass 173.21 g·mol−1 Melting point 154.5 to 157 °C (310.1 to 314.6 °F; 427.6 to 430.1 K) (hydrochloride) Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
SCH-50911 is a selective GABAB antagonist .[ 1] Its main applications are in pharmacology research.
SCH-50911 also acts as an anticonvulsant under normal conditions. SCH-50911 induces acute withdrawal syndrome in GHB-dependent rats, similar to the delirium tremens seen in human alcohol withdrawal , and can precipitate convulsions in GHB-dependent animals.[ 2]
References ^ Blythin DJ, Kuo SC, Shue HJ, McPhail AT, Chapman RW, Kreutner W, et al. (July 1996). "Substituted morpholine-2S-acetic acid derivatives: Sch 50911 and related compounds as novel GABAB antagonists". Bioorganic & Medicinal Chemistry Letters . 6 (13): 1529– 34. doi :10.1016/S0960-894X(96)00267-3 . ^ Quang LS, Colombo G, Lobina C, Maccioni P, Orru A, Gessa GL, et al. (August 2006). "Evaluation for the withdrawal syndrome from gamma-hydroxybutyric acid (GHB), gamma-butyrolactone (GBL), and 1,4-butanediol (1,4-BD) in different rat lines". Annals of the New York Academy of Sciences . 1074 (1): 545– 58. Bibcode :2006NYASA1074..545Q . doi :10.1196/annals.1369.055 . PMID 17105952 . S2CID 86383425 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor Positive modulators (abridged; see here for a full list): α-EMTBL Alcohols (e.g., drinking alcohol , 2M2B ) Anabolic steroids Avermectins (e.g., ivermectin ) Barbiturates (e.g., phenobarbital ) Benzodiazepines (e.g., diazepam ) Bromide compounds (e.g., potassium bromide ) Carbamates (e.g., meprobamate ) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) ) Etazepine Etifoxine Fenamates (e.g., mefenamic acid ) Flavonoids (e.g., apigenin , hispidulin ) Fluoxetine Flupirtine Imidazoles (e.g., etomidate ) Kava constituents (e.g., kavain ) Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC ) Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon )) Norfluoxetine Petrichloral Phenols (e.g., propofol ) Phenytoin Piperidinediones (e.g., glutethimide ) Propanidid Pyrazolopyridines (e.g., etazolate ) Quinazolinones (e.g., methaqualone ) Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin ) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) ) Topiramate Valerian constituents (e.g., valerenic acid ) Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane ) Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems ) Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO ) BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil ) Flavonoids (e.g., amentoflavone , oroxylin A ) Flumazenil Fluoroquinolones (e.g., ciprofloxacin ) Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide ) Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin ) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor Negative modulators: Compound 14
See also Receptor/signaling modulators GABAA receptor positive modulators GABA metabolism/transport modulators