Epiboxidine
- Investigational
- (1R,4S,6S)-6-(3-Methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
- 188895-96-7
- 5747670
- 4677635
- XI646L2ARJ
- DTXSID20172258
- Interactive image
- CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3
- InChI=1S/C10H14N2O/c1-6-4-10(13-12-6)8-5-7-2-3-9(8)11-7/h4,7-9,11H,2-3,5H2,1H3/t7-,8-,9+/m0/s1
- Key:GEEFPQBPVBFCSD-XHNCKOQMSA-N
Epiboxidine is a chemical compound which acts as a partial agonist at neural nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes. It was developed as a less toxic analogue of the potent frog-derived alkaloid epibatidine, which is around 200 times stronger than morphine as an analgesic but produces extremely dangerous toxic nicotinic side effects.
Epiboxidine is around one-tenth as potent as epibatidine as an α4β2 agonist, but has around the same potency as an α3β4 agonist. It has only one-tenth of the analgesic power of epibatidine, but is also much less toxic.[1][2][3]
Uses
Despite its decreased potency and toxicity compared to epibatidine, epiboxidine itself is still too toxic to be developed as a drug for use in humans. It is used in scientific research[4] and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.[5][6][7]
See also
References
- ^ Rizzi L, Dallanoce C, Matera C, Magrone P, Pucci L, Gotti C, et al. (August 2008). "Epiboxidine and novel-related analogues: a convenient synthetic approach and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes" (PDF). Bioorganic & Medicinal Chemistry Letters. 18 (16): 4651–4. doi:10.1016/j.bmcl.2008.07.016. hdl:2434/59291. PMID 18644719.
- ^ Dallanoce C, Matera C, De Amici M, Rizzi L, Pucci L, Gotti C, et al. (July 2012). "The enantiomers of epiboxidine and of two related analogs: synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors". Chirality. 24 (7): 543–51. doi:10.1002/chir.22052. PMID 22566097.
- ^ Badio B, Garraffo HM, Plummer CV, Padgett WL, Daly JW (February 1997). "Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine". European Journal of Pharmacology. 321 (2): 189–94. doi:10.1016/S0014-2999(96)00939-9. PMID 9063687.
- ^ Yan X, Zhao B, Butt CM, Debski EA (December 2006). "Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway". The European Journal of Neuroscience. 24 (11): 3026–42. doi:10.1111/j.1460-9568.2006.05204.x. PMID 17156364. S2CID 25993659.
- ^ Fitch RW, Pei XF, Kaneko Y, Gupta T, Shi D, Federova I, Daly JW (January 2004). "Homoepiboxidines: further potent agonists for nicotinic receptors". Bioorganic & Medicinal Chemistry. 12 (1): 179–90. doi:10.1016/j.bmc.2003.10.015. PMID 14697783.
- ^ Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1775–8. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.
- ^ Armstrong A, Bhonoah Y, Shanahan SE (October 2007). "Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine". The Journal of Organic Chemistry. 72 (21): 8019–24. doi:10.1021/jo701536a. PMID 17867705.
- v
- t
- e
- 3-Fluoromethcathinone
- 3,4-DMMC
- 4-BMC
- 4-CMC
- 4-Methylbuphedrone
- 4-Methylcathinone
- 4-MEAP
- 4-Methylpentedrone
- Amfepramone
- Benzedrone
- Buphedrone
- Bupropion
- Butylone
- Cathinone
- Dimethylcathinone
- Ethcathinone
- Ethylone
- Flephedrone
- Hexedrone
- Isoethcathinone
- Mephedrone
- Methcathinone
- Methedrone
- Methylenedioxycathinone
- Methylone
- Mexedrone
- N-Ethylbuphedrone
- N-Ethylhexedrone
- Pentedrone
- Pentylone
- Phthalimidopropiophenone
- A-84,543
- A-366,833
- ABT-202
- ABT-418
- AR-R17779
- Altinicline
- Anabasine
- Arecoline
- Bradanicline
- Cotinine
- Cytisine
- Dianicline
- Epibatidine
- Epiboxidine
- GTS-21
- Ispronicline
- Nicotine
- PHA-543,613
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- Sazetidine A
- SIB-1553A
- SSR-180,711
- TC-1698
- TC-1827
- TC-2216
- Tebanicline
- UB-165
- Varenicline
- WAY-317,538
- 1-(4-Methylphenyl)-2-aminobutane
- 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
- 2-Fluoroamphetamine
- 2-Fluoromethamphetamine
- 2-OH-PEA
- 2-Phenyl-3-aminobutane
- 2,3-MDA
- 3-Fluoroamphetamine
- 3-Fluoroethamphetamine
- 3-Methoxyamphetamine
- 3-Methylamphetamine
- 4-Fluoroamphetamine
- 4-Fluoromethamphetamine
- 4-MA
- 4-MMA
- 4-MTA
- 6-FNE
- AL-1095
- Alfetamine
- a-Ethylphenethylamine
- Amfecloral
- Amfepentorex
- Amidephrine
- 2-Amino-1,2-dihydronaphthalene
- 2-Aminoindane
- 5-(2-Aminopropyl)indole
- 2-Aminotetralin
- Acridorex
- Amphetamine (Dextroamphetamine, Levoamphetamine)
- Amphetaminil
- Arbutamine
- β-Methylphenethylamine
- β-Phenylmethamphetamine
- Benfluorex
- Benzphetamine
- BDB
- BOH
- 3-Benzhydrylmorpholine
- BPAP
- Camfetamine
- Cathine
- Chlorphentermine
- Cilobamine
- Cinnamedrine
- Clenbuterol
- Clobenzorex
- Cloforex
- Clortermine
- Cypenamine
- D-Deprenyl
- Denopamine
- Dimethoxyamphetamine
- Dimethylamphetamine
- Dobutamine
- DOPA (Dextrodopa, Levodopa)
- Dopamine
- Dopexamine
- Droxidopa
- EBDB
- Ephedrine
- Epinephrine
- Epinine
- Etafedrine
- Ethylnorepinephrine
- Etilamfetamine
- Etilefrine
- Famprofazone
- Fencamfamin
- Fencamine
- Fenethylline
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Fenproporex
- Feprosidnine
- Fludorex
- Formetorex
- Furfenorex
- Gepefrine
- Hexapradol
- HMMA
- Hordenine
- 4-Hydroxyamphetamine
- 5-Iodo-2-aminoindane
- Ibopamine
- Indanylamphetamine
- Iofetamine
- Isoetarine
- Isoprenaline
- L-Deprenyl (Selegiline)
- Lefetamine
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA (tenamfetamine)
- MDBU
- MDEA
- MDMA (midomafetamine)
- MDMPEA
- MDOH
- MDPR
- MDPEA
- Mefenorex
- Mephentermine
- Metanephrine
- Metaraminol
- Mesocarb
- Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
- Methoxamine
- Methoxyphenamine
- MMA
- Methoxyphenamine
- MMDA
- MMDMA
- MMMA
- Morforex
- N,alpha-Diethylphenylethylamine
- N,N-Dimethylphenethylamine
- Naphthylamphetamine
- Nisoxetine
- Norepinephrine
- Norfenefrine
- Norfenfluramine
- Normetanephrine
- L-Norpseudoephedrine
- Octopamine
- Orciprenaline
- Ortetamine
- Oxifentorex
- Oxilofrine
- PBA
- PCA
- PCMA
- PHA
- Pentorex
- Phenatine
- Phenpromethamine
- Phentermine
- Phenylalanine
- Phenylephrine
- Phenylpropanolamine
- Pholedrine
- PIA
- PMA
- PMEA
- PMMA
- PPAP
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Ropinirole
- Salbutamol (Levosalbutamol)
- Sibutramine
- Solriamfetol
- Synephrine
- Theodrenaline
- Tiflorex
- Tranylcypromine
- Tyramine
- Tyrosine
- Xylopropamine
- Zylofuramine
- 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
- 2-Benzylpiperidine
- 2-Methyl-3-phenylpiperidine
- 3,4-Dichloromethylphenidate
- 4-Benzylpiperidine
- 4-Fluoromethylphenidate
- 4-Methylmethylphenidate
- Desoxypipradrol
- Difemetorex
- Diphenylpyraline
- Ethylnaphthidate
- Ethylphenidate
- Methylnaphthidate
- Isopropylphenidate
- JZ-IV-10
- Methylphenidate (Dexmethylphenidate)
- Nocaine
- Phacetoperane
- Pipradrol
- Propylphenidate
- Serdexmethylphenidate
- SCH-5472
- 4-fluorotropacocaine
- 4'-Fluorococaine
- Altropane (IACFT)
- Brasofensine
- CFT (WIN 35,428)
- β-CIT (RTI-55)
- Cocaethylene
- Cocaine
- Dichloropane (RTI-111)
- Difluoropine
- FE-β-CPPIT
- FP-β-CPPIT
- Ioflupane (123I)
- Norcocaine
- PIT
- PTT
- RTI-31
- RTI-32
- RTI-51
- RTI-112
- RTI-113
- RTI-120
- RTI-121 (IPCIT)
- RTI-126
- RTI-150
- RTI-177
- RTI-229
- RTI-336
- RTI-354
- RTI-371
- RTI-386
- Salicylmethylecgonine
- Tesofensine
- Troparil (β-CPT, WIN 35,065-2)
- Tropoxane
- WF-23
- WF-33
- 2-MDP
- 3,3-Diphenylcyclobutanamine
- Amfonelic acid
- Amineptine
- Amiphenazole
- Atipamezole
- Atomoxetine
- Bemegride
- Benzydamine
- BTQ
- BTS 74,398
- Centanafadine
- Ciclazindol
- Clofenciclan
- Cropropamide
- Crotetamide
- D-161
- Desipramine
- Diclofensine
- Dimethocaine
- Efaroxan
- Etamivan
- Fenisorex
- Fenpentadiol
- Gamfexine
- Gilutensin
- GSK1360707F
- GYKI-52895
- Hexacyclonate
- Idazoxan
- Indanorex
- Indatraline
- JNJ-7925476
- Lazabemide
- Leptacline
- Lomevactone
- LR-5182
- Mazindol
- Meclofenoxate
- Medifoxamine
- Mefexamide
- Methamnetamine
- Methastyridone
- Methiopropamine
- Naphthylaminopropane
- Nefopam
- Nikethamide
- Nomifensine
- O-2172
- Oxaprotiline
- PNU-99,194
- PRC200-SS
- Rasagiline
- Rauwolscine
- Rubidium chloride
- Setazindol
- Tametraline
- Tandamine
- Thiopropamine
- Thiothinone
- Trazium
- UH-232
- Yohimbine