Gacyclidine (GK-11) is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP).[1][2]
[edit] Synthesis
The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with Na-N3 in trichloroacetic acid to yield the azide (V). The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrile to provide the target compound as a diastereomeric mixture. [3]
[edit] See also
[edit] References
- ^ Hirbec H, Gaviria M, Vignon J. Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor. CNS Drug Reviews. 2001 Summer;7(2):172-98.
- ^ Hirbec H, Mausset AL, Kamenka JM, Privat A, Vignon J. Re-evaluation of phencyclidine low-affinity or "non-NMDA" binding sites. J Neurosci Res. 2002 May 1;68(3):305-14.
- ^ Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines. Jean-Marc Kamenka et al, 1993. "[1]"
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Psychedelics
5-HT2AR agonists |
- Lysergamides: AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAM-57
- Diallyllysergamide
- Ergometrine
- ETH-LAD
- LAE-32
- LSA
- LSD
- LSH
- LPD-824
- LSM-775
- Lysergic acid 2-butyl amide
- Lysergic acid 2,4-dimethylazetidide
- Lysergic acid 3-pentyl amide
- Methylergometrine
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- MLD-41
- PARGY-LAD
- PRO-LAD
Phenethylamines: Aleph
- 2C-B
- 2C-B-Dragonfly
- 2C-B-FLY
- 2C-C-FLY
- 2C-D-FLY
- 2C-E-FLY
- 2C-I-FLY
- 2CBFly-NBOMe
- 2C-T-7-FLY
- 2C-C
- 2C-C-NBOMe
- 2C-CN-NBOMe
- 2C-D
- 2CD-5EtO
- 2C-D-NBOMe
- 2C-E
- 2C-EF
- 2C-E-NBOMe
- 2C-F
- 2C-F-NBOMe
- 2C-G
- 2C-G-NBOMe
- 2C-H-NBOMe
- 2C-I
- 2C-N
- 2C-N-NBOMe
- 2C-O
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- 2C-P
- 2C-T
- 2C-T-2
- 2C-T-4
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- 2C-T-7
- 2C-T-7-NBOH
- 2C-T-8
- 2C-T-9
- 2C-T-13
- 2C-T-15
- 2C-T-17
- 2C-T-21
- 2C-TFM
- 2C-TFM-NBOMe
- 2C-YN
- 2CBCB-NBOMe
- 25B-NBOMe
- 25I-NBMD
- 25I-NBOH
- 25I-NBOMe
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- 5-APDB
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- Br-DFLY
- DESOXY
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- DOB
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- DOC
- DOEF
- DOET
- DOF
- DOI
- DOM
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- DOPR
- DOTFM
- Escaline
- Ganesha
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- IAP
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- Lophophine
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- MMDA
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- TCB-2
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Piperazines: pFPP
- TMFPP
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine
- 2,N,N-TMT
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- 4-HO-5-MeO-DMT
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- 4-Acetoxy-DIPT
- 4-Acetoxy-DMT
- 4-Acetoxy-DPT
- 4-Acetoxy-MiPT
- 4-HO-DPT
- 4-HO-MET
- 4-Propionyloxy-DMT
- 4-HO-MPMI
- 5-Me-MIPT
- 5-N,N-TMT
- 5-AcO-DMT
- 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
- 7,N,N-TMT
- α,N,N-TMT
- α-ET
- α-MT
- AL-37350A
- 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
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Dissociatives
NMDAR antagonists |
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Deliriants
mAChR antagonists |
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- Adamantanes: Amantadine
- Memantine
- Rimantadine; Aminotetralins: 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232; Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959; Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Lisuride
- LSD
- Pergolide; Dihydrexidine derivatives: 2-OH-NPA
- A-86,929
- Ciladopa
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine; Others: A-68,930
- A-77636
- A-412,997
- ABT-670
- ABT-724
- Aplindore
- Apomorphine
- Aripiprazole
- Bifeprunox
- BP-897
- CY-208,243
- Dizocilpine
- Etilevodopa
- Flibanserin
- Ketamine
- Melevodopa
- Modafinil
- Pardoprunox
- Phencyclidine
- PD-128,907
- PD-168,077
- PF-219,061
- Piribedil
- Pramipexole
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Rotigotine
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- SKF-89,145
- Sumanirole
- Terguride
- Umespirone
- WAY-100,635
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| Ionotropic |
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- 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
- 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
- Loperamide
- Memantine
- Meperidine (Pethidine)
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- 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
- ACPC
- 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
- Enflurane
- Ethanol (Alcohol)
- Halothane
- Isoflurane
- Methoxyflurane
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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| Metabotropic |
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Transporter
inhibitors |
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| Others |
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