L-687,384

L-687,384
Clinical data
ATC code	none;
Identifiers
	IUPAC name 1'-benzylspiro[2,3-dihydro-1H-naphthalene-4,4'-piperidine];
CAS Number	95417-67-7 ;
PubChem CID	125328;
ChemSpider	111534 ;
UNII	NVE9K68QA3;
ChEMBL	ChEMBL303336;
CompTox Dashboard (EPA)	DTXSID30241828 ;
Chemical and physical data
Formula	C21H25N
Molar mass	291.438 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3ccccc3CN2CCC1(CC2)CCCc4c1cccc4;
	InChI InChI=1S/C21H25N/c1-2-7-18(8-3-1)17-22-15-13-21(14-16-22)12-6-10-19-9-4-5-11-20(19)21/h1-5,7-9,11H,6,10,12-17H2 ; Key:MLDCBJPLHBPJET-UHFFFAOYSA-N ;
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L-687,384 is a sigma receptor agonist, selective for the σ₁ subtype,^[1] as well as an NMDA antagonist.^[2]

References

^ Bergeron R, Debonnel G (February 1997). "Effects of low and high doses of selective sigma ligands: further evidence suggesting the existence of different subtypes of sigma receptors". Psychopharmacology. 129 (3): 215–24. doi:10.1007/s002130050183. PMID 9084059. S2CID 24537111.
^ McLarnon J, Sawyer D, Church J (June 1994). "The actions of L-687,384, a sigma receptor ligand, on NMDA-induced currents in cultured rat hippocampal pyramidal neurons". Neuroscience Letters. 174 (2): 181–4. doi:10.1016/0304-3940(94)90016-7. PMID 7526288. S2CID 10876486.
^ Quaglia W, Giannella M, Piergentili A, Pigini M, Brasili L, Di Toro R, Rossetti L, Spampinato S, Melchiorre C. 1'-Benzyl-3,4-dihydrospiro[2H-1- benzothiopyran-2,4'-piperidine] (spipethiane), a potent and highly selective sigma1 ligand. J Med Chem. 1998 May 7;41(10):1557-60. doi: 10.1021/jm970740r. PMID 9572880.

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[pmid9084059-1] Bergeron R, Debonnel G (February 1997). "Effects of low and high doses of selective sigma ligands: further evidence suggesting the existence of different subtypes of sigma receptors". Psychopharmacology. 129 (3): 215–24. doi:10.1007/s002130050183. PMID 9084059. S2CID 24537111.

[pmid7526288-2] McLarnon J, Sawyer D, Church J (June 1994). "The actions of L-687,384, a sigma receptor ligand, on NMDA-induced currents in cultured rat hippocampal pyramidal neurons". Neuroscience Letters. 174 (2): 181–4. doi:10.1016/0304-3940(94)90016-7. PMID 7526288. S2CID 10876486.

[3] Quaglia W, Giannella M, Piergentili A, Pigini M, Brasili L, Di Toro R, Rossetti L, Spampinato S, Melchiorre C. 1'-Benzyl-3,4-dihydrospiro[2H-1- benzothiopyran-2,4'-piperidine] (spipethiane), a potent and highly selective sigma1 ligand. J Med Chem. 1998 May 7;41(10):1557-60. doi: 10.1021/jm970740r. PMID 9572880.

[1]

[2]

[3]

v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists: AC-927 BD-1008 BD-1067 CM-156 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Zervimesine (CT-1812) Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

L-687,384

L-687,384

L-687,384

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Hub overview

Root Wikipedia Article

L-687,384

See also

References

Clinical data

ATC code	none
Identifiers
IUPAC name 1'-benzylspiro[2,3-dihydro-1H-naphthalene-4,4'-piperidine]
CAS Number	95417-67-7^Y
PubChem CID	125328
ChemSpider	111534^N
UNII	NVE9K68QA3
ChEMBL	ChEMBL303336
CompTox Dashboard (EPA)	DTXSID30241828
Chemical and physical data
Formula	C₂₁H₂₅N
Molar mass	291.438 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3ccccc3CN2CCC1(CC2)CCCc4c1cccc4
InChI InChI=1S/C21H25N/c1-2-7-18(8-3-1)17-22-15-13-21(14-16-22)12-6-10-19-9-4-5-11-20(19)21/h1-5,7-9,11H,6,10,12-17H2^N Key:MLDCBJPLHBPJET-UHFFFAOYSA-N^N
^NY (what is this?) (verify)