Dexoxadrol

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Dexoxadrol

Systematic (IUPAC) name
(2S)-2-[(4S)-2,2-di(phenyl)-1,3-dioxolan-4-yl]piperidine
Clinical data
Legal status	Legal
Identifiers
CAS number	6495-46-1^N
ATC code	None
PubChem	CID 3034023
ChemSpider	2298576^Y
UNII	Verifiedfields = changed JY5N9F45AG Verifiedfields = changed^N
ChEMBL	CHEMBL1165411^Y
Chemical data
Formula	C₂₀H₂₃N O₂
Mol. mass	309.40 g/mol
SMILES O1C[C@@H](OC1(c2ccccc2)c3ccccc3)[C@H]4NCCCC4
InChI InChI=1S/C20H23NO2/c1-3-9-16(10-4-1)20(17-11-5-2-6-12-17)22-15-19(23-20)18-13-7-8-14-21-18/h1-6,9-12,18-19,21H,7-8,13-15H2/t18-,19+/m0/s1^Y Key:HGKAMARNFGKMLC-RBUKOAKNSA-N^Y
N (what is this?) (verify)

Dexoxadrol (Dioxadrol) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. Dexoxadrol, along with another related drug etoxadrol, were developed as analgesics for use in humans, but development was discontinued after patients reported side effects such as nightmares and hallucinations.^[1]^[2]

References

↑ Sax, M.; Wünsch, B. (2006). "Relationships between the structure of dexoxadrol and etoxadrol analogues and their NMDA receptor affinity". Current Topics in Medicinal Chemistry 6 (7): 723–732. doi:10.2174/156802606776894483. PMID 16719812.
↑ Aepkers, M.; Wünsch, B. (2005). "Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol". Bioorganic and Medicinal Chemistry 13 (24): 6836–6849. doi:10.1016/j.bmc.2005.07.030. PMID 16169732.

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-LAD CYP-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 Lysergic acid 2-butyl amide LSZ Lysergic acid 3-pentyl amide Methylergometrine Methylisopropyllysergamide Methysergide N1-Methyl-lysergic acid diethylamide PARGY-LAD PRO-LAD

Phenethylamines	Aleph 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY βk-2C-B 2C-C 2C-C-FLY 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 2C-E-NBOMe 2C-EF 2C-F 2C-F-NBOMe 2C-G 2C-G-NBOMe 2C-H-NBOMe 2C-I 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 2C-T-4-NBOMe 2C-T-7 2C-T-7-FLY 2C-T-7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-17 2C-T-19 2C-T-21 2C-TFM 25TFM-NBOMe 2C-YN 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBOMe 2C-P-NBOMe 3C-AL 3C-E 3C-P 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY DESOXY DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Juncosamine Lophophine Macromerine MDA MDEA MDMA Mescaline Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA NBOMe-mescaline Proscaline TCB-2 TFMFly TMA

Piperazines	pFPP TMFPP mCPP

Tryptamines	1-Methyl-5-methoxy-diisopropyltryptamine 2,N,N-TMT 4,5-DHP-AMT 4,5-DHP-DMT 4-Acetoxy-DALT 4-Acetoxy-DET 4-Acetoxy-DiPT 4-Acetoxy-DMT 4-Acetoxy-DPT 4-Acetoxy-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Iprocin MET Miprocin MiPT Norbaeocystin PiPT Psilocin Psilocybin

Others	AL-38022A Elemicin Ibogaine Myristicin Noribogaine Voacangine

Dissociatives
NMDAR antagonists

Adamantanes	Amantadine Memantine Rimantadine

Arylcyclohexylamines	3-MeO-PCP 4-MeO-PCP Dieticyclidine Diphenidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine Neramexane PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others	2-MDP 8A-PDHQ Aptiganel Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 JWH-018 JWH-030 JWH-073 JWH-081 JWH-200 JWH-250 Levonantradol Nabilone Nabitan Parahexyl WIN 55,212-2

D₂R agonists

Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Piribedil
Pramipexole
Ropinirole
Rotigotine
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists

Inhalants
Mixed MOA

Aliphatic hydrocarbons
- Butane
- Gasoline
- Kerosene
- Propane
Aromatic hydrocarbons
- Toluene
Ethers
- Diethyl ether
- Enflurane
Haloalkanes
- Chlorofluorocarbons
- Chloroform

κOR agonists

MAO inhibitors

σR agonists

Others

Glutamatergics

Ionotropic

AMPA	Agonists: 5-Fluorowillardiine AMPA Domoic acid Quisqualic acid; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 CX-691 CX-717 Diazoxide HCTZ IDRA-21 LY-392,098 LY-404,187 LY-451,395 LY-451,646 LY-503,430 Org 26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Sunifiram Unifiram Antagonists: ATPO Barbiturates BGG492 Caroverine CNQX DNQX GYKI-52466 NBQX Perampanel Talampanel Tezampanel Topiramate; Negative allosteric modulators: GYKI-53,655

NMDA	Agonists: Glutamate/acite site competitive agonists: Aspartate Glutamate Homoquinolinic acid Ibotenic acid NMDA Quinolinic acid Tetrazolylglycine; Glycine site agonists: ACBD ACPC ACPD Alanine CCG Cycloserine DHPG Fluoroalanine Glycine GLYX-13 HA-966 L-687,414 Milacemide Sarcosine Serine Tetrazolylglycine; Polyamine site agonists: Acamprosate Spermidine Spermine Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP LY-233,053 LY-235,959 LY-274,614 MDL-100,453 Midafotel (d-CPPene) NPC-12,626 NPC-17,742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Noncompetitive antagonists: ARR-15,896 Caroverine Dexanabinol FPL-12495 FR-115,427 Hodgkinsine Magnesium MDL-27,266 NPS-1506 Psychotridine Zinc; Uncompetitive pore blockers: 2-MDP 3-MeO-PCP 8A-PDHQ Alaproclate Amantadine Aptiganel ARL-12,495 ARL-15,896-AR ARL-16,247 Budipine Delucemine Dexoxadrol Dextrallorphan Dieticyclidine Dizocilpine Endopsychosin Esketamine Etoxadrol Eticyclidine Gacyclidine Ibogaine Indantadol Ketamine Ketobemidone Lanicemine Loperamide Memantine Meperidine (Pethidine) Methadone (Levomethadone) Methorphan (Dextromethorphan Levomethorphan) Methoxetamine Milnacipran Morphanol (Dextrorphan Levorphanol) NEFA Neramexane Nitromemantine Nitrous oxide Noribogaine Orphenadrine PCPr Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Riluzole Rimantadine Rolicyclidine Sabeluzole Tenocyclidine Tiletamine Tramadol Xenon; Glycine site antagonists: ACEA-1021 ACEA-1328 ACC Carisoprodol CGP-39653 CKA DCKA Felbamate Gavestinel GV-196,771 Kynurenic acid L-689,560 L-701,324 Lacosamide Licostinel LU-73,068 MDL-105,519 Meprobamate MRZ 2/576 PNQX ZD-9379; NR2B subunit antagonists: Besonprodil CO-101,244 (PD-174,494) CP-101,606 Eliprodil Haloperidol Ifenprodil Isoxsuprine Nylidrin Ro8-4304 Ro25-6981 Traxoprodil; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Acamprosate Diethylenetriamine Huperzine A Putrescine Ro 25-6981; Unclassified/unsorted antagonists: Chloroform Diethyl ether Diphenidine Enflurane Ethanol (alcohol) Halothane Isoflurane Methoxyflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Xylene

Kainate	Agonists: 5-Iodowillardiine ATPA Domoic acid Kainic acid LY-339,434 SYM-2081 Antagonists: BGG492 CNQX DNQX LY-382,884 NBQX NS102 Tezampanel Topiramate UBP-302; Negative allosteric modulators: NS-3763

Metabotropic

Group I	Agonists: Non-selective: ACPD DHPG Quisqualic acid; mGlu1-selective: Ro01-6128 Ro67-4853 Ro67-7476 VU-71; mGlu5-selective: ADX-47273 CDPPB CHPG DFB VU-1545 Antagonists: Non-selective: MCPG NPS-2390; mGlu1-selective: BAY 36-7620 CPCCOEt LY-367,385 LY-456,236; mGlu5-selective: CTEP Dipraglurant DMeOB LY-344,545 SIB-1757 SIB-1893; Negative allosteric modulators: Fenobam MPEP MTEP GRN-529

Group II	Agonists: Non-selective: CBiPES DCG-IV Eglumegad LY-379,268 LY-404,039 LY-487,379 MGS-0028; mGlu2-selective: BINA LY-566,332 Antagonists: Non-selective: APICA EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039; mGlu2-selective: PCCG-4 mGlu3-selective: CECXG; Negative allosteric modulators: RO4491533

Group III	Agonists: Non-selective: L-AP4; mGlu4-selective: PHCCC VU-001,171 VU-0155,041; mGlu7-selective: AMN082; mGlu8-selective: DCPG Antagonists: Non-selective: CPPG MAP4 MSOP MPPG MTPG UBP-1112; mGlu7-selective: MMPIP

Transporter
inhibitors

EAATs	DHKA PDC WAY-213,613

vGluTs	7-CKA Evans blue

Others

Precursors	L-Glutamine

Cofactors	α-Ketoglutaric acid Iron Sulfur Vitamin B2 (as FAD and FMN) Vitamin B3 (as NADPH)

Others	L-Theanine

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