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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/04/16 21:58:10」(JST)
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Cyclazocine
|
Systematic (IUPAC) name |
3-(Cyclopropylmethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
or
2-Cyclopropylmethyl-2'-hydroxy-5,9-dimethyl-6,7-benzomorphan |
Clinical data |
Legal status
|
|
Routes of
administration
|
Oral |
Identifiers |
CAS Registry Number
|
7346-09-0 N |
ATC code
|
None |
PubChem |
CID 19143 |
IUPHAR ligand |
1604 |
ChemSpider |
18063 Y |
UNII |
J5W1B1159C Y |
KEGG |
D03618 Y |
ChEMBL |
CHEMBL56585 N |
Chemical data |
Formula |
C18H25NO |
Molecular mass
|
271.40 g/mol |
SMILES
- Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)C)C
|
InChI
-
InChI=1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3 Y
Key:YQYVFVRQLZMJKJ-UHFFFAOYSA-N Y
|
N (what is this?) (verify) |
Cyclazocine is a mixed opioid agonist/antagonist related to dezocine, pentazocine and phenazocine. This family of opioid drugs is called the benzomorphans or benzazocines.[1] It is a KOR agonist and MOR partial agonist, and also has high affinity for the DOR.[2]
Use
Research into the use of cyclazocine for the treatment of bipolar patients with depression was undertaken by Fink and colleagues (1970). It showed that 8 out of 10 patients experienced moderate improvement.
Research during the 1960s and 1970s into the possible use of cyclazocine for management of pain, and later for assisting treatment of narcotic addiction was severely hampered by the drug's psychotomimetic, dysphoric, and hallucinatory effects.[3]
See also
References
- ^ Archer, S.; Glick, S. D.; Bidlack, J. M. (1996). "Cyclazocine Revisited". Neurochemical Research 21 (11): 1369–1373. doi:10.1007/BF02532378. PMID 8947927.
- ^ Bidlack JM, Cohen DJ, McLaughlin JP, Lou R, Ye Y, Wentland MP (July 2002). "8-Carboxamidocyclazocine: a long-acting, novel benzomorphan". J. Pharmacol. Exp. Ther. 302 (1): 374–80. doi:10.1124/jpet.302.1.374. PMID 12065740.
- ^ Freedman, A. M.; Fink, M.; Sharoff, R.; Zaks, A. (1967). "Cyclazocine and Methadone in Narcotic Addiction" (pdf). The Journal of the American Medical Association 202 (3): 191–194. doi:10.1001/jama.1967.03130160065011. PMID 6072354.
Hallucinogens
|
|
Psychedelics
5-HT2AR agonists |
Lysergamides
|
- AL-LAD
- ALD-52
- BU-LAD
- IP-LAD
- Diallyllysergamide
- Dimethyllysergamide
- Ergometrine
- ETH-LAD
- LAE-32
- LPD-824
- LSA
- LSD
- LSD-Pip
- LSH
- LSM-775
- 2-Butyllysergamide
- LSZ
- 3-Pentyllysergamide
- Methylergometrine
- Methylisopropyllysergamide
- Methysergide
- MLD-41
- PARGY-LAD
- PRO-LAD
|
|
Phenethylamines
|
|
|
Piperazines
|
|
|
Tryptamines
|
- 1-Me-5-MeO-DiPT
- 2,N,N-TMT
- 4,5-DHP-α-MT
- 4,5-DHP-DMT
- 4-AcO-DALT
- 4-AcO-DET
- 4-AcO-DiPT
- 4-AcO-DMT
- 4-AcO-DPT
- 4-AcO-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
- Ibogaine
- Iprocin
- MET
- Miprocin
- MiPT
- Norbaeocystin
- Noribogaine
- PiPT
- Psilocin
- Psilocybin
- Voacangine
|
|
Others
|
- AL-38022A
- ALPHA
- Dimemebfe
- M-ALPHA
- RH-34
|
|
|
Dissociatives
NMDAR antagonists |
Adamantanes
|
- Amantadine
- Memantine
- Rimantadine
|
|
Arylcyclohexylamines
|
- 3-MeO-PCP
- 4-MeO-PCP
- Dieticyclidine
- Esketamine
- Ethketamine
- Eticyclidine
- Gacyclidine
- Ketamine
- Methoxetamine
- Methoxyketamine
- PCPr
- Phencyclidine
- Rolicyclidine
- Tenocyclidine
- Tiletamine
|
|
Morphinans
|
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Racemethorphan
- Racemorphan
|
|
Others
|
- 2-MDP
- 8A-PDHQ
- Aptiganel
- Dexoxadrol
- Diphenidine
- Dizocilpine
- Etoxadrol
- Ibogaine
- Methoxphenidine
- Midafotel
- NEFA
- Neramexane
- Nitrous oxide
- Noribogaine
- Perzinfotel
- Remacemide
- Selfotel
- Xenon
|
|
|
Deliriants
mAChR antagonists |
- Atropine
- Benactyzine
- Benzatropine
- Benzydamine
- Biperiden
- BRN-1484501
- Brompheniramine
- BZ
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Chloropyramine
- Chlorphenamine
- Clemastine
- CS-27349
- Cyclizine
- Cyproheptadine
- Dicycloverine
- Dimenhydrinate
- Diphenhydramine
- Ditran
- Doxylamine
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Elemicin
- Flavoxate
- Hyoscyamine
- JB-318
- JB-336
- Meclozine
- Mepyramine
- Myristicin
- Orphenadrine
- Oxybutynin
- Pheniramine
- Phenyltoloxamine
- Procyclidine
- Promethazine
- Scopolamine
- Tolterodine
- Trihexyphenidyl
- Tripelennamine
- Triprolidine
- WIN-2299
|
|
Miscellaneous |
Cannabinoids
CB1R agonists
|
Phytocannabinoids
|
- Cannabinol
- THC (Dronabinol)
- THCV
- (Cannabidiol has different mechanism of action)
|
|
Synthetic
|
- 4-HTMPIPO
- 5F-PB-22
- AB-001
- AB-005
- A-836,339
- AB-CHMINACA
- AB-FUBINACA
- AB-PINACA
- ADB-FUBINACA
- ADB-PINACA
- ADBICA
- AM-630
- AM-679
- AM-694
- AM-1220
- AM-1221
- AM-1235
- AM-1241
- AM-1248
- AM-2201
- AM-2232
- AM-2233
- APICA
- APINACA
- CB-13
- CP 47,497
- CP 55,244
- CP 55,940
- DMHP
- HU-210
- HU-308
- JWH-007
- JWH-015
- JWH-018
- JWH-019
- JWH-030
- JWH-073
- JWH-081
- JWH-098
- JWH-116
- JWH-122
- JWH-149
- JWH-167
- JWH-182
- JWH-193
- JWH-198
- JWH-200
- JWH-203
- JWH-210
- JWH-250
- JWH-251
- JWH-398
- JWH-424
- JTE 7-31
- JTE-907
- Levonantradol
- MAM-2201
- MDA-19
- MN-25
- NESS-0327
- NESS-040C5
- Nabilone
- Nabitan
- Org 28611
- Parahexyl
- QUCHIC
- QUPIC
- RCS-4
- RCS-8
- SDB-006
- STS-135
- THC-O-acetate
- THC-O-phosphate
- UR-144
- WIN 55,212-2
- XLR-11
|
|
|
D2R agonists
|
- Apomorphine
- 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).
|
|
GABAAR agonists
|
- Eszopiclone
- Gaboxadol
- Ibotenic acid
- Muscimol
- Zaleplon
- Zolpidem
- Zopiclone
|
|
Inhalants
Mixed MOA
|
- Aliphatic hydrocarbons
- Butane
- Gasoline
- Kerosene
- Propane
- Aromatic hydrocarbons
- Ethers
- Haloalkanes
- Chlorofluorocarbons
- Chloroform
|
|
κOR agonists
|
- 2-EMSB
- 2-MMSB
- Alazocine
- Bremazocine
- Butorphanol
- Cyclazocine
- Cyprenorphine
- Dextrallorphan
- Dezocine
- Enadoline
- Herkinorin
- HZ-2
- Ibogaine
- Ketazocine
- LPK-26
- Metazocine
- Nalbuphine
- Nalorphine
- Noribogaine
- Pentazocine
- Phenazocine
- Salvinorin A
- Spiradoline
- Tifluadom
- U-50488
- U-69,593
|
|
MAO inhibitors
|
- Harmaline
- Harmine
- Tetrahydroharmine
- Yohimbine
|
|
σR agonists
|
- DMT
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Noscapine
|
|
Others
|
- Glaucine
- Isoaminile
- Pukateine
|
|
|
Opioidergics
|
|
Receptor
(ligands) |
MOR |
|
|
DOR |
|
|
KOR |
- Agonists: 6'-GNTI
- 8-CAC
- 18-MC
- 14-Methoxymetopon
- β-Chlornaltrexamine
- β-Funaltrexamine
- Adrenorphin (metorphamide)
- Akuuamicine
- Alazocine
- Allomatrine
- Asimadoline
- BAM-12P
- BAM-18P
- BAM-22P
- Big dynorphin
- Bremazocine
- BRL-52537
- Butorphanol
- BW-373U86
- Cebranopadol
- Ciprefadol
- CR845
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Diamorphine (heroin)
- Diacetylnalorphine
- Dihydroetorphine
- Dihydromorphine
- Dynorphin A
- Dynorphin B (rimorphin)
- Enadoline
- Eptazocine
- Erinacine E
- Ethylketazocine
- Etorphine
- FE 200665 (CR665)
- Fedotozine
- Fentanyl
- Gemazocine
- GR-89696
- GR-103545
- Hemorphin-4
- Herkinorin
- HS665
- Hydromorphone
- HZ-2
- Ibogaine
- ICI-199,441
- ICI-204,448
- Ketamine
- Ketazocine
- Laudanosine
- Leumorphin (dynorphin B-29)
- Levallorphan
- Levorphanol
- Lofentanil
- LPK-26
- Lufuradom
- Matrine
- MB-1C-OH
- Menthol
- Metazocine
- Metkefamide
- Mianserin
- Mirtazapine
- Morphine
- Moxazocine
- N-MPPP
- Nalbuphine
- NalBzOH
- Nalfurafine
- Nalmefene
- Nalorphine
- Naltriben
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- O-Desmethyltramadol
- Oripavine
- Oxilorphan
- Oxycodone
- Pentazocine
- Pethidine (meperidine)
- Phenazocine
- Proxorphan
- RB-64
- Salvinorin A (salvia)
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- SKF-10047
- Spiradoline (U-62,066)
- Thienorphine
- Tifluadom
- Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
- U-50,488
- U-54,494A
- U-69,593
- Xorphanol
- Antagonists: 4′-Hydroxyflavanone
- 4',7-Dihydroxyflavone
- 5'-GNTI
- 6β-Naltrexol
- 6β-Naltrexol-d4
- β-Chlornaltrexamine
- ALKS-5461
- Amentoflavone
- ANTI
- Apigenin
- Arodyne
- AT-076
- Binaltorphimine
- BU09059
- Buprenorphine
- Catechin
- Catechin gallate
- CERC-501 (LY-2456302)
- Clocinnamox
- Dezocine
- DIPPA
- Diprenorphine
- EGC
- ECG
- Epicatechin
- Hyperoside
- JDTic
- LY-255582
- LY-2196044
- LY-2459989
- LY-2795050
- Methylnaltrexone
- ML190
- ML350
- MR-2266
- Naloxone
- Naltrexone
- Naltrindole
- Naringenin
- Norbinaltorphimine
- Noribogaine
- Pawhuskin A
- PF-4455242
- Quadazocine
- Taxifolin
- UPHIT
- Zyklophin
- Unknown/unsorted: Akuammicine
- Akuammine
- Coronaridine
- Cyproterone acetate
- Dihydroakuuamine
- Ibogamine
- Tabernanthine
|
|
NOP |
- Agonists: (Arg14,Lys15)Nociceptin
- ((pF)Phe4)Nociceptin(1-13)NH2
- (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2
- Ac-RYYRWK-NH2
- Ac-RYYRIK-NH2
- Buprenorphine
- Cebranopadol
- Dihydroetorphine
- Etorphine
- MCOPPB
- MT-7716
- NNC 63-0532
- Nociceptin (orphanin FQ)
- Nociceptin (1-11)
- Nociceptin (1-13)NH2
- Norbuprenorphine
- Ro64-6198
- Ro65-6570
- SCH-221510
- SR-8993
- SR-16435
- Antagonists: (Nphe1)Nociceptin(1-13)NH2
- AT-076
- BAN-ORL-24
- J-113397
- JTC-801
- LY-2940094
- NalBzOH
- Nociceptin (1-7)
- Nocistatin
- SB-612111
- SR-16430
- Thienorphine
- Trap-101
- UFP-101
|
|
Unsorted /
unknown |
- β-Casomorphins
- Amidorphin
- BAM-20P
- Cytochrophin-4
- Deprolorphin
- Gliadorphin (gluteomorphin)
- Gluten exorphins
- Hemorphins
- Kava constituents
- MEAGL
- MEAP
- NEM
- Neoendorphins
- Peptide B
- Peptide E
- Peptide F
- Peptide I
- Rubiscolins
- Soymorphins
|
|
|
Enzyme
(inhibitors) |
Enkephalinase |
- BL-2401
- Candoxatril
- D -Phenylalanine
- Ecadotril
- Kelatorphan
- Racecadotril (acetorphan)
- RB-101
- RB-120
- RB-3007
- Selank
- Semax
- Spinorphin
- Thiorphan
- Tynorphin
- Ubenimex (bestatin)
|
|
|
Others |
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
|
|
See also: Neuropeptidergics • Peptidergics
|
|
Sigmaergics
|
|
Receptor
(ligands)
|
σ (1, 2)
|
- Agonists: 3-MeO-PCE
- 3-MeO-PCP
- 3-PPP
- 4-MeO-PCP
- 4-IBP
- 4-PPBP
- Afobazole
- Alazocine
- Amitriptyline
- Arketamine
- BD-1,008
- Berberine
- Captodiame
- Citalopram
- Clorgiline
- Cocaine
- Cyclazocine
- DHEA
- DHEA-S
- Desipramine
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Dimemorfan
- DMT
- DTG
- EMD-57,445
- Escitalopram
- Fluoxetine
- Fluvoxamine
- Heroin
- Igmesine
- Imipramine
- JO-1,784
- Ketamine
- L-687,384
- Lu 28-179
- MDMA
- Metaphit
- Methamphetamine
- Methoxetamine
- Methylphenidate
- Morphine
- Naluzotan
- Noscapine
- OPC-14,523
- Opipramol
- PB-28
- PD-144,415
- Pentazocine
- Pentoxyverine
- Phencyclidine
- PRE-084
- Pregnenolone
- Pregnenolone sulfate
- RTI-55
- SA-4503
- Siramesine
- Tenocyclidine
- Venlafaxine
- Antagonists: BD-1,047
- BD-1,063
- BMY-14,802
- E-5,842
- Haloperidol
- Lamotrigine
- MIN-101
- NE-100
- Progesterone
- Rimcazole
- S1RA (E-52862)
- Sertraline
- SM-21
- Unknown/unsorted: 4C-T-2
- 5-MeO-DiPT
- 18-MC
- β-Endopsychosin
- Clocapramine
- DiPT
- DPT
- Gevotroline
- Ibogaine
- Noribogaine
- TMA; Allosteric modulators: SKF-83,959
|
|
|
English Journal
- Acid-mediated ring-expansion reaction of N-aryl-2-vinylazetidines: synthesis and unanticipated reactivity of tetrahydrobenzazocines.
- Shimizu T1, Koya S, Yamasaki R, Mutoh Y, Azumaya I, Katagiri K, Saito S.
- The Journal of organic chemistry.J Org Chem.2014 May 16;79(10):4367-77. doi: 10.1021/jo500249c. Epub 2014 Apr 28.
- The aza-Clasen rearrangement of N-aryl-2-vinylazetidines has been explored. N-Aryl-2-vinylazetidines were transformed to corresponding tetrahydrobenzazocines in good yields. Unexpectedly, the tetrahydrobenzazocine was unstable and readily isomerized to vinyltetrahydroquinoline in the presence of aci
- PMID 24731245
- Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 8. High affinity ligands for opioid receptors in the picomolar Ki range: oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) analogues of 8-CAC.
- Wentland MP1, Jo S, Gargano JM, VanAlstine MA, Cohen DJ, Bidlack JM.
- Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2012 Dec 15;22(24):7340-4. doi: 10.1016/j.bmcl.2012.10.081. Epub 2012 Oct 27.
- N-[2-(4'-methoxy[1,1'-biphenyl]-4-yl)ethyl]-8-CAC (1) is a high affinity (K(i)=0.084 nM) ligand for the μ opioid receptor and served as the lead compound for this study. Analogues of 1 were made in hopes of identifying an SAR within a series of oxygenated (distal) phenyl derivatives. A number of ne
- PMID 23142613
- Latent inhibition in an insect: the role of aminergic signaling.
- Fernández VM1, Giurfa M, Devaud JM, Farina WM.
- Learning & memory (Cold Spring Harbor, N.Y.).Learn Mem.2012 Nov 16;19(12):593-7. doi: 10.1101/lm.028167.112.
- Latent inhibition (LI) is a decrement in learning performance that results from the nonreinforced pre-exposure of the to-be-conditioned stimulus, in both vertebrates and invertebrates. In vertebrates, LI development involves dopamine and serotonin; in invertebrates there is yet no information. We st
- PMID 23161448
Japanese Journal
- 水上 善博
- 滋賀大学教育学部紀要. 3, 自然科学 54, 35-39, 2004
- … calculations.Calculated opiates are morphine, oxymorphone, levorphanol, nalorphine, naloxone, levallorphan, heroin, codeine, etorphine, dihydromorphine, normorphine, pentazocine, apomorphine, buprenorphine, butorpahnol, dihydrocodeine, oxycodone, thebaine, bremazocine, cyclazocine, ketocyclazocine, naloxazone, naltrexazone, oxymorphazone.25 molecules have common molecular skeleton that includes 10 atoms(one nitrogen atom, one oxygen atom and 8 carbon atoms).Electron densities of HOMO on these 10 atoms are used to perform principal component …
- NAID 110001183530
- 水上 善博,清水 英里佳
- 情報化学討論会・構造活性相関シンポジウム講演要旨集 tokusi(0), JP31-JP31, 2001
- … Calculated molecules are morphine, oxymorphone, levorphanol, nalorphine, naloxone, levallorphan, heroin, codeine, etorphine, dihydromorphine, normorphine, pentazocine, apomorphine, buprenorphine, butorpahnol, dihydrocodeine, oxycodone, thebaine, bremazocine, cyclazocine, ketocyclazocine, naloxazone, naltrexazone, naltrexone, oxymorphazone. …
- NAID 130004575375
- 水上 善博,清水 英里佳
- 情報化学討論会講演要旨集 tokusi(0), JP31-JP31, 2001
- … Calculated molecules are morphine, oxymorphone, levorphanol, nalorphine, naloxone, levallorphan, heroin, codeine, etorphine, dihydromorphine, normorphine, pentazocine, apomorphine, buprenorphine, butorpahnol, dihydrocodeine, oxycodone, thebaine, bremazocine, cyclazocine, ketocyclazocine, naloxazone, naltrexazone, naltrexone, oxymorphazone. …
- NAID 130004575179
Related Links
- Cyclazocine definition, a synthetic nonnarcotic and nonaddictive analgesic, C 18 H 25 NO, that blocks the effects of morphine or morphinelike drugs: used to treat heroin or morphine addiction. See more. Dictionary.com Word of the ...
- :an analgesic drug C 18 H 25 NO that inhibits the effect of morphine and related addictive drugs and is used in the treatment of drug addiction ... Seen and Heard What made you want to look up cyclazocine? Please tell us where you ...
Related Pictures
![Keto Cyclazocine](https://1mg.info/0/7/u/2546.jpg)
![Cyclazocine structure.svg](https://1mg.info/0/7/u/2547.jpg)
![Chemical structure of Cyclazocine.](https://1mg.info/0/7/u/2548.jpg)
![CYCLAZOCINE ,Cyclazocine (USAN](https://1mg.info/0/7/u/2549.jpg)
![cyclazocine](https://1mg.info/0/7/u/2550.jpg)
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