Perzinfotel: Difference between revisions

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Revision as of 11:47, 1 August 2022 editFfffrr (talk \| contribs)Extended confirmed users99,459 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper ← Previous edit		Revision as of 12:29, 11 May 2023 edit undoM97uzivatel (talk \| contribs)Extended confirmed users6,578 editsNo edit summaryNext edit →
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	{{Short description\|Chemical compound}}		{{Short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
	\| Verifiedfields = changed		\|Verifiedfields = changed
	\| Watchedfields = changed		\|Watchedfields = changed
	\| verifiedrevid = 443223642		\|verifiedrevid = 443223642
	\| IUPAC_name = 2-(8,9-Dioxo-2,6-diazabicyclonon-1(7)-en-2-yl)ethylphosphonic acid		\|IUPAC_name = 2-(8,9-Dioxo-2,6-diazabicyclonon-1(7)-en-2-yl)ethylphosphonic acid
	\| image = Perzinfotel.svg		\|image = Perzinfotel.svg
	\| width = 150		\|width = 150
		⚫	\|CAS_number_Ref = {{cascite\|correct\|??}}

		⚫	\|CAS_number = 144912-63-0
	<!--Clinical data-->
	\| ~~tradename~~ =		\|ATC_prefix = none
		⚫	\|PubChem = 6918236
	\| routes_of_administration =
		⚫	\|DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}

		⚫	\|UNII_Ref = {{fdacite\|correct\|FDA}}
	<!--Pharmacokinetic data-->
		⚫	\|UNII = FX5AUU7Z8T
	\| metabolism =
		⚫	\|KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| elimination_half-life =
		⚫	\|KEGG = D05447
	\| excretion =
		⚫	\|ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}

		⚫	\|ChemSpiderID = 5293443
	<!--Identifiers-->
		⚫	\|C=9 \| H=13 \| N=2 \| O=5 \| P=1
⚫	\| CAS_number_Ref = {{cascite\|correct\|??}}
		⚫	\|smiles = C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O
⚫	\| CAS_number = 144912-63-0
		⚫	\|StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| ATC_prefix = none
		⚫	\|StdInChI = 1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16)
⚫	\| PubChem = 6918236
		⚫	\|StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\|StdInChIKey = BDABGOLMYNHHTR-UHFFFAOYSA-N
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| UNII = FX5AUU7Z8T
⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
⚫	\| KEGG = D05447
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
⚫	\| ChemSpiderID = 5293443

	<!--Chemical data-->
⚫	\| C=9 \| H=13 \| N=2 \| O=5 \| P=1
⚫	\| smiles = C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O
⚫	\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	\| StdInChI = 1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16)
⚫	\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	\| StdInChIKey = BDABGOLMYNHHTR-UHFFFAOYSA-N
	}}		}}
	'''Perzinfotel''' ('''EAA-090''') is a drug which acts as a potent ].<ref>{{cite journal \| vauthors = Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, Miller TL, Tasse RP, Zaleska MM, Moyer JA \| display-authors = 6 \| title = Design and synthesis of non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral alpha-amino acid bioisostere \| journal = Journal of Medicinal Chemistry \| volume = 41 \| issue = 2 \| pages = 236–46 \| date = January 1998 \| pmid = 9457246 \| doi = 10.1021/jm970504g }}</ref> It has ] effects and has been investigated for the treatment of ],<ref>{{cite journal \| vauthors = Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S ~~\| display-authors = 6~~ \| title = Characterization of two novel N-methyl-D-aspartate antagonists: EAA-090 (2-non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride) \| journal = The Journal of Pharmacology and Experimental Therapeutics \| volume = 310 \| issue = 2 \| pages = 563–70 \| date = August 2004 \| pmid = 15075380 \| doi = 10.1124/jpet.104.066092 \| s2cid = 25505657 }}</ref> but lacks ] effects.<ref>{{cite journal \| vauthors = Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S \| title = Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity \| journal = The Journal of Pharmacology and Experimental Therapeutics \| volume = 313 \| issue = 3 \| pages = 1379–86 \| date = June 2005 \| pmid = 15764736 \| doi = 10.1124/jpet.105.084467 \| s2cid = 12989500 }}</ref> Nevertheless, it shows a good safety profile compared to older drugs, although further development of this drug has been discontinued.<ref>{{cite web \| title = Perzinfotel \| url = http://adisinsight.springer.com/drugs/800009946 \| work = Adis International Ltd. \| publisher = Springer Nature Switzerland AG }}</ref>		'''Perzinfotel''' ('''EAA-090''') is a drug which acts as a potent ].<ref>{{cite journal \| vauthors = Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, Miller TL, Tasse RP, Zaleska MM, Moyer JA \| display-authors = 6 \| title = Design and synthesis of non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral alpha-amino acid bioisostere \| journal = Journal of Medicinal Chemistry \| volume = 41 \| issue = 2 \| pages = 236–46 \| date = January 1998 \| pmid = 9457246 \| doi = 10.1021/jm970504g }}</ref> It has ] effects and has been investigated for the treatment of ],<ref>{{cite journal \| vauthors = Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S \| title = Characterization of two novel N-methyl-D-aspartate antagonists: EAA-090 (2-non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride) \| journal = The Journal of Pharmacology and Experimental Therapeutics \| volume = 310 \| issue = 2 \| pages = 563–70 \| date = August 2004 \| pmid = 15075380 \| doi = 10.1124/jpet.104.066092 \| s2cid = 25505657 }}</ref> but lacks ] effects.<ref>{{cite journal \| vauthors = Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S \| title = Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity \| journal = The Journal of Pharmacology and Experimental Therapeutics \| volume = 313 \| issue = 3 \| pages = 1379–86 \| date = June 2005 \| pmid = 15764736 \| doi = 10.1124/jpet.105.084467 \| s2cid = 12989500}}</ref> Nevertheless, it shows a good safety profile compared to older drugs, although further development of this drug has been discontinued.<ref>{{cite web \| title = Perzinfotel \| url = http://adisinsight.springer.com/drugs/800009946 \| work = Adis International Ltd. \| publisher = Springer Nature Switzerland AG }}</ref>

	Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.<ref name="BaudyButera2009">{{cite journal \| vauthors = Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, Magolda R, Sze JY, Brandt MR, Cummons TA, Kowal D, Pangalos MN, Zupan B, Hoffmann M, May M, Mugford C, Kennedy J, Childers WE \| display-authors = 6 \| title = Prodrugs of perzinfotel with improved oral bioavailability \| journal = Journal of Medicinal Chemistry \| volume = 52 \| issue = 3 \| pages = 771–8 \| date = February 2009 \| pmid = 19146418 \| doi = 10.1021/jm8011799 }}</ref>		Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.<ref name="BaudyButera2009">{{cite journal \| vauthors = Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, Magolda R, Sze JY, Brandt MR, Cummons TA, Kowal D, Pangalos MN, Zupan B, Hoffmann M, May M, Mugford C, Kennedy J, Childers WE \| display-authors = 6 \| title = Prodrugs of perzinfotel with improved oral bioavailability \| journal = Journal of Medicinal Chemistry \| volume = 52 \| issue = 3 \| pages = 771–8 \| date = February 2009 \| pmid = 19146418 \| doi = 10.1021/jm8011799 }}</ref>
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	{{Hallucinogens}}		{{Hallucinogens}}
	{{Ionotropic glutamate receptor modulators}}		{{Ionotropic glutamate receptor modulators}}
		⚫	{{nervous-system-drug-stub}}

	]		]
	]		]
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⚫	{{nervous-system-drug-stub}}

Revision as of 12:29, 11 May 2023

Chemical compound Pharmaceutical compound

Perzinfotel
Clinical data

ATC code	none
Identifiers
IUPAC name 2-(8,9-Dioxo-2,6-diazabicyclonon-1(7)-en-2-yl)ethylphosphonic acid
CAS Number	144912-63-0
PubChem CID	6918236
ChemSpider	5293443
UNII	FX5AUU7Z8T
KEGG	D05447
CompTox Dashboard (EPA)	DTXSID70162846
ECHA InfoCard	100.222.780
Chemical and physical data
Formula	C₉H₁₃N₂O₅P
Molar mass	260.186 g·mol
3D model (JSmol)	Interactive image
SMILES C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O
InChI InChI=1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16) Key:BDABGOLMYNHHTR-UHFFFAOYSA-N
(what is this?) (verify)

Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist. It has neuroprotective effects and has been investigated for the treatment of stroke, but lacks analgesic effects. Nevertheless, it shows a good safety profile compared to older drugs, although further development of this drug has been discontinued.

Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.

References

Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, et al. (January 1998). "Design and synthesis of non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral alpha-amino acid bioisostere". Journal of Medicinal Chemistry. 41 (2): 236–46. doi:10.1021/jm970504g. PMID 9457246.
Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S (August 2004). "Characterization of two novel N-methyl-D-aspartate antagonists: EAA-090 (2-non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride)". The Journal of Pharmacology and Experimental Therapeutics. 310 (2): 563–70. doi:10.1124/jpet.104.066092. PMID 15075380. S2CID 25505657.
Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S (June 2005). "Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity". The Journal of Pharmacology and Experimental Therapeutics. 313 (3): 1379–86. doi:10.1124/jpet.105.084467. PMID 15764736. S2CID 12989500.
"Perzinfotel". Adis International Ltd. Springer Nature Switzerland AG.
Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, et al. (February 2009). "Prodrugs of perzinfotel with improved oral bioavailability". Journal of Medicinal Chemistry. 52 (3): 771–8. doi:10.1021/jm8011799. PMID 19146418.

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25x-NB	25B-NB 25C-NB
25x-NB3OMe	25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe
25x-NB4OMe	25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe
25x-NBF	25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-NBF
25x-NBMD	25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD
25x-NBOH	25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH
25x-NBOMe	25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe
Atypical structures	25B-N1POMe 25B-NAcPip 25B-NB23DM 25B-NB25DM 25C-NBCl 25C-NBOEt 25C-NBOiPr 25I-N2Nap1OH 25I-N3MT2M 25I-N4MT3M 25I-NB34MD 25I-NBAm 25I-NBBr 25I-NBMeOH 25I-NBTFM 2CBCB-NBOMe 2CBFly-NBOMe 4-EA-NBOMe 5-APB-NBOMe 5MT-NBOMe C30-NBOMe DOB-NBOMe DOI-NBOMe FECIMBI-36 MDPEA-NBOMe N-Ethyl-2C-B NBOMe-escaline NBOMe-mescaline ZDCM-04

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AM-x	AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545
CP x	CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940
HU-x	HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345
JWH-x	JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424
Misc. designer cannabinoids	4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

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v t e Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor	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
KARTooltip Kainate receptor	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
NMDARTooltip N-Methyl-D-aspartate receptor	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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