ACPD

Names
Preferred IUPAC name

1-Aminocyclopentane-1,3-dicarboxylic acid[1]

Identifiers

CAS Number

* 39026-63-6 N
* 56827-69-1 (1R,3S) Y
* 111900-32-4 (1S,3R) Y

3D model (JSmol)

* Interactive image

Abbreviations  | ACPD
ChEMBL |

* ChEMBL168278 N

ChemSpider |

* 1270 N
* 201559 (1R,3R) Y
* 66220 (1R,3S) Y
* 94574 (1S,3R) Y
* 5036967 (1S,3S) N

MeSH | 1-amino-1,3-dicarboxycyclopentane

PubChem CID

* 1310
* 44381972 (1S)
* 231345 (1R,3R)
* 73537 (1R,3S)
* 104766 (1S,3R)
* 6604704 (1S,3S)

RTECS number |

* GY4060000 (1S,3R)

InChI

* InChI=1S/C7H11NO4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4H,1-3,8H2,(H,9,10)(H,11,12) N

Key: YFYNOWXBIBKGHB-UHFFFAOYSA-N N

SMILES

* NC1(CCC(C1)C(O)=O)C(O)=O

Properties

Chemical formula

| C7H11NO4
Molar mass | 173.168 g·mol−1
Appearance  | White crystals

Solubility in water

| 20 g dm−3
Solubility in ethanol | 240 mg dm−3
log P | -0.709
Acidity (pKa)  | 2.112
Basicity (pKb)  | 11.885
Isoelectric point | 2.84
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H312, H315, H319, H332, H335

GHS precautionary statements

| P261, P280, P305+351+338

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

1-Amino-1,3-dicarboxycyclopentane (ACPD) is a chemical compound that binds to the metabotropic glutamate receptor (mGluR),[2] acting as a mGluR agonist. ACPD is a rigid analogue of the neurotransmitter glutamate and does not activate ionotropic glutamate receptors.[3] However, it has been reported to be an agonist of the glycine site of the NMDA receptor.[citation needed] ACPD can induce convulsions in neonatal rats.[4]

## References

1. ↑ "1-amino-1,3-dicarboxycyclopentane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1310.
2. ↑ "1S,3R-ACPD-sensitive (metabotropic) [3H]glutamate receptor binding in membranes". Neurosci. Lett. 145 (1): 100–4. September 1992. doi:10.1016/0304-3940(92)90213-Q. PMID 1461560.
3. ↑ "(trans)-1-amino-cyclopentyl-1,3-dicarboxylate stimulates quisqualate phosphoinositide-coupled receptors but not ionotropic glutamate receptors in striatal neurons and Xenopus oocytes". Mol. Pharmacol. 38 (1): 1–6. July 1990. PMID 2164627. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=2164627.
4. ↑ "Seizures and brain injury in neonatal rats induced by 1S,3R-ACPD, a metabotropic glutamate receptor agonist". J. Neurosci. 13 (10): 4445–55. October 1993. doi:10.1523/JNEUROSCI.13-10-04445.1993. PMID 8410197.

Glutamate receptor modulators

* v
* t
* e

Ionotropic glutamate receptor modulators

AMPAR|

* Agonists: Main site agonists: 5-Fluorowillardiine
* Acromelic acid (acromelate)
* AMPA
* BOAA
* Domoic acid
* Glutamate
* Ibotenic acid
* Proline
* Quisqualic acid
* Willardiine; Positive allosteric modulators: Aniracetam
* BIIB-104 (PF-04958242)
* 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
* 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

KAR|

* 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

NMDAR|

* 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
* DHEA (prasterone)
* DHEA sulfate (prasterone sulfate)
* Epipregnanolone sulfate
* 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

* v
* t
* e

Metabotropic glutamate receptor modulators

Group I|

| mGluR1|

* Agonists: ACPD
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* Ro01-6128
* Ro67-4853
* Ro67-7476
* VU-71
* Theanine

* Antagonists: BAY 36-7620
* CPCCOEt
* Cyclothiazide
* LY-367,385
* LY-456,236
* MCPG
* NPS-2390

|

mGluR5|

* Agonists: ACPD
* ADX-47273
* CDPPB
* CHPG
* DFB
* DHPG
* Glutamate
* Ibotenic acid
* Quisqualic acid
* VU-1545

* Antagonists: CTEP
* DMeOB
* LY-344,545
* Mavoglurant
* MCPG
* NPS-2390
* Remeglurant
* SIB-1757
* SIB-1893; Negative allosteric modulators: Basimglurant
* Dipraglurant
* Fenobam
* GRN-529
* MPEP
* MTEP
* Raseglurant

Group II|

| mGluR2|

* Agonists: BINA
* CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* LY-566,332
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149)

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039
* PCCG-4; Negative allosteric modulators: Decoglurant
* RO4491533

|

mGluR3|

* Agonists: CBiPES
* DCG-IV
* Eglumegad
* Glutamate
* Ibotenic acid
* LY-379,268
* LY-404,039 (pomaglumetad)
* LY-487,379
* MGS-0028
* Pomaglumetad methionil (LY-2140023)
* Talaglumetad

* Antagonists: APICA
* CECXG
* EGLU
* HYDIA
* LY-307,452
* LY-341,495
* MCPG
* MGS-0039; Negative allosteric modulators: Decoglurant
* RO4491533

Group III|

| mGluR4|

* Agonists: Glutamate
* L-AP4
* PHCCC
* VU-001,171
* VU-0155,041; Positive allosteric modulators: Foliglurax
* MPEP

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

|

mGluR6|

* Agonists: Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

mGluR7|

* Agonists: AMN082
* Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MMPIP
* MPPG
* MSOP
* MTPG
* UBP-1112

mGluR8|

* Agonists: DCPG
* Glutamate
* L-AP4

* Antagonists: CPPG
* MAP4
* MPPG
* MSOP
* MTPG
* UBP-1112

See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:ACPD&oldid=362377"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H332]: Harmful if inhaled
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AMPAR]: α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
*[KAR]: Kainate receptor
*[NMDAR]: N-Methyl-D-aspartate receptor
*[DHEA]: Dehydroepiandrosterone
*[mGluR1]: Metabotropic glutamate receptor 1
*[mGluR5]: Metabotropic glutamate receptor 5
*[mGluR2]: Metabotropic glutamate receptor 2
*[mGluR3]: Metabotropic glutamate receptor 3
*[mGluR4]: Metabotropic glutamate receptor 4
*[mGluR6]: Metabotropic glutamate receptor 6
*[mGluR7]: Metabotropic glutamate receptor 7
*[mGluR8]: Metabotropic glutamate receptor 8