Homocysteic acid
![]() L-Homocysteic acid | |
Names | |
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IUPAC name (2S)-2-Amino-4-sulfobutanoic acid | |
Other names Homocysteate | |
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Properties | |
Chemical formula | C4H9NO5S |
Molar mass | 183.18 g·mol−1 |
Appearance | white or colorless solid |
Melting point | 261 °C (502 °F; 534 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
Homocysteic acid is the organosulfur compound with the formula HO3SCH2CH2CH(NH2)CO2H. A white solid, it is sulfonic acid-containing non-proteinogenic amino acid. It is aanalog of glutamic acid and is a potent NMDA receptor agonist.[1][2] It is related to homocysteine, a by-product of methionine metabolism.
Homocysteic acid is prepared by the oxidation of homocystine with aqueous bromine.[3]
References
- ^ Grandes, P; Kq, KQD; Morino, P; Cuénod, M; Streit, P (1991). "Homocysteate, an Excitatory Transmitter Candidate Localized in Glia". The European Journal of Neuroscience. 3 (12): 1370–1373. doi:10.1111/j.1460-9568.1991.tb00070.x. PMID 12106235. S2CID 23139077.
- ^ Yuzaki, M; Connor, JA (1999). "Characterization of L-homocysteate-induced currents in Purkinje cells from wild-type and NMDA receptor knockout mice". Journal of Neurophysiology. 82 (5): 2820–6. doi:10.1152/jn.1999.82.5.2820. PMID 10561449. S2CID 16073533.
- ^ Watkins, J. C. (1962). "The Synthesis of Some Acidic Amino Acids Possessing Neuropharmacological Activity". Journal of Medicinal and Pharmaceutical Chemistry. 5 (6): 1187–1199. doi:10.1021/jm01241a010. PMID 14056452.
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- Agonists: Main site agonists: 5-Fluorowillardiine
- Acromelic acid (acromelate)
- AMPA
- BOAA
- Domoic acid
- Glutamate
- Ibotenic acid
- Proline
- Quisqualic acid
- Willardiine; Positive allosteric modulators: Aniracetam
- Cyclothiazide
- CX-516
- CX-546
- CX-614
- Farampator (CX-691, ORG-24448)
- CX-717
- CX-1739
- CX-1942
- Diazoxide
- Hydrochlorothiazide (HCTZ)
- IDRA-21
- LY-392098
- LY-395153
- LY-404187
- LY-451646
- LY-503430
- Mibampator (LY-451395)
- Nooglutyl
- ORG-26576
- Oxiracetam
- PEPA
- Pesampator (BIIB-104, PF-04958242)
- Piracetam
- Pramiracetam
- S-18986
- Tulrampator (S-47445, CX-1632)
- Antagonists: ACEA-1011
- ATPO
- Becampanel
- Caroverine
- CNQX
- Dasolampanel
- DNQX
- Fanapanel (MPQX)
- GAMS
- Kaitocephalin
- Kynurenic acid
- Kynurenine
- Licostinel (ACEA-1021)
- NBQX
- PNQX
- Selurampanel
- Tezampanel
- Theanine
- Topiramate
- YM90K
- Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
- Cyclopropane
- Enflurane
- Ethanol (alcohol)
- Evans blue
- GYKI-52466
- GYKI-53655
- Halothane
- Irampanel
- Isoflurane
- Perampanel
- Pregnenolone sulfate
- Sevoflurane
- Talampanel; Unknown/unsorted antagonists: Minocycline
- Agonists: Main site agonists: 5-Bromowillardiine
- 5-Iodowillardiine
- Acromelic acid (acromelate)
- AMPA
- ATPA
- Domoic acid
- Glutamate
- Ibotenic acid
- Kainic acid
- LY-339434
- Proline
- Quisqualic acid
- SYM-2081; Positive allosteric modulators: Cyclothiazide
- Diazoxide
- Enflurane
- Halothane
- Isoflurane
- Antagonists: ACEA-1011
- CNQX
- Dasolampanel
- DNQX
- GAMS
- Kaitocephalin
- Kynurenic acid
- Licostinel (ACEA-1021)
- LY-382884
- NBQX
- NS102
- Selurampanel
- Tezampanel
- Theanine
- Topiramate
- UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
- Enflurane
- Ethanol (alcohol)
- Evans blue
- NS-3763
- Pregnenolone sulfate
- Agonists: Main site agonists: AMAA
- Aspartate
- Glutamate
- Homocysteic acid (L-HCA)
- Homoquinolinic acid
- Ibotenic acid
- NMDA
- Proline
- Quinolinic acid
- Tetrazolylglycine
- Theanine; Glycine site agonists: β-Fluoro-D-alanine
- ACBD
- ACC (ACPC)
- ACPD
- AK-51
- Apimostinel (NRX-1074)
- B6B21
- CCG
- D-Alanine
- D-Cycloserine
- D-Serine
- DHPG
- Dimethylglycine
- Glycine
- HA-966
- L-687414
- L-Alanine
- L-Serine
- Milacemide
- Neboglamine (nebostinel)
- Rapastinel (GLYX-13)
- Sarcosine; Polyamine site agonists: Neomycin
- Spermidine
- Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol
- DHEATooltip Dehydroepiandrosterone (prasterone)
- DHEA sulfate (prasterone sulfate)
- Epipregnanolone sulfate
- Plazinemdor
- Pregnenolone sulfate
- SAGE-201
- SAGE-301
- SAGE-718
- Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- Kaitocephalin
- LY-233053
- LY-235959
- LY-274614
- MDL-100453
- Midafotel (d-CPPene)
- NPC-12626
- NPC-17742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101)
- 5,7-DCKA
- 7-CKA
- ACC
- ACEA-1011
- ACEA-1328
- Apimostinel (NRX-1074)
- AV-101
- Carisoprodol
- CGP-39653
- CNQX
- D-Cycloserine
- DNQX
- Felbamate
- Gavestinel
- GV-196771
- Harkoseride
- Kynurenic acid
- Kynurenine
- L-689560
- L-701324
- Licostinel (ACEA-1021)
- LU-73068
- MDL-105519
- Meprobamate
- MRZ 2/576
- PNQX
- Rapastinel (GLYX-13)
- ZD-9379; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Diethylenetriamine
- Huperzine A
- Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP
- 3-HO-PCP
- 3-MeO-PCE
- 3-MeO-PCMo
- 3-MeO-PCP
- 4-MeO-PCP
- 8A-PDHQ
- 18-MC
- α-Endopsychosin
- Alaproclate
- Alazocine (SKF-10047)
- Amantadine
- Aptiganel
- Argiotoxin-636
- Arketamine
- ARL-12495
- ARL-15896-AR
- ARL-16247
- Budipine
- Coronaridine
- Delucemine (NPS-1506)
- Dexoxadrol
- Dextrallorphan
- Dextromethadone
- Dextromethorphan
- Dextrorphan
- Dieticyclidine
- Diphenidine
- Dizocilpine
- Ephenidine
- Esketamine
- Etoxadrol
- Eticyclidine
- Fluorolintane
- Gacyclidine
- Ibogaine
- Ibogamine
- Indantadol
- Ketamine
- Ketobemidone
- Lanicemine
- Levomethadone
- Levomethorphan
- Levomilnacipran
- Levorphanol
- Loperamide
- Memantine
- Methadone
- Methorphan
- Methoxetamine
- Methoxphenidine
- Milnacipran
- Morphanol
- NEFA
- Neramexane
- Nitromemantine
- Noribogaine
- Norketamine
- Orphenadrine
- PCPr
- PD-137889
- Pethidine (meperidine)
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tabernanthine
- Tenocyclidine
- Tiletamine
- Tramadol; Ifenprodil (NR2B) site antagonists:
- Besonprodil
- Buphenine (nylidrin)
- CO-101244 (PD-174494)
- Eliprodil
- Haloperidol
- Isoxsuprine
- Radiprodil (RGH-896)
- Rislenemdaz (CERC-301, MK-0657)
- Ro 8-4304
- Ro 25-6981
- Safaprodil
- Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004
- MPX-007
- TCN-201
- TCN-213; Cations: Hydrogen
- Magnesium
- Zinc; Alcohols/volatile anesthetics/related: Benzene
- Butane
- Chloroform
- Cyclopropane
- Desflurane
- Diethyl ether
- Enflurane
- Ethanol (alcohol)
- Halothane
- Hexanol
- Isoflurane
- Methoxyflurane
- Nitrous oxide
- Octanol
- Sevoflurane
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Urethane
- Xenon
- Xylene; Unknown/unsorted antagonists: ARR-15896
- Bumetanide
- Caroverine
- Conantokin
- D-αAA
- Dexanabinol
- Flufenamic acid
- Flupirtine
- FPL-12495
- FR-115427
- Furosemide
- Hodgkinsine
- Ipenoxazone (MLV-6976)
- MDL-27266
- Metaphit
- Minocycline
- MPEP
- Niflumic acid
- Pentamidine
- Pentamidine isethionate
- Piretanide
- Psychotridine
- Transcrocetin (saffron)
- Unsorted: Allosteric modulators: AGN-241751
- See also: Receptor/signaling modulators
- Metabotropic glutamate receptor modulators
- Glutamate metabolism/transport modulators
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