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| Watchedfields = changed
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| verifiedrevid = 432325202
| verifiedrevid = 432325202
| ImageFile = Evoxine.png
| ImageFile = Evoxine.svg
| ImageSize = 200px
| ImageAlt =
| ImageAlt =
| IUPACName = (±)-1-(4,8-Dimethoxyfuro[2,3-''b'']quinolin-7-yl)oxy-3-methylbutane-2,3-diol
| IUPACName = (±)-1-(4,8-Dimethoxyfuro[2,3-''b'']quinolin-7-yl)oxy-3-methylbutane-2,3-diol
| OtherNames = Haploperine
| OtherNames = Haploperine
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 522-11-2
| CASNo = 522-11-2
| PubChem = 73416
| PubChem = 73416
| ChEMBL = 1416006
| SMILES = CC(C)(C(COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC)O)O
| SMILES = CC(C)(C(COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC)O)O
| ATC_prefix = none
| ATC_suffix =
| ChemSpiderID = 66130
| InChI = 1/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
| InChI = 1/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
| InChIKey = FGANMDNHTVJAHL-UHFFFAOYAV
| InChIKey = FGANMDNHTVJAHL-UHFFFAOYAV
| StdInChI = 1S/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
| StdInChI = 1S/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
| StdInChIKey = FGANMDNHTVJAHL-UHFFFAOYSA-N
| StdInChIKey = FGANMDNHTVJAHL-UHFFFAOYSA-N}}
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|Section2={{Chembox Properties
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}}
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| C=18 | H=21 | N=1 | O=6
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| Section2 = {{Chembox Properties
| Appearance =
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| C=18 | H=21 | N=1 | O=6
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|Section3={{Chembox Hazards
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| MainHazards =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| FlashPt =
| AutoignitionPt = }}
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|Section5={{Chembox Pharmacology
| Autoignition = }}
| ATCCode_prefix = none
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| Section5 = {{Chembox Pharmacology

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'''Evoxine''' ('''haploperine''') is a [[furoquinoline alkaloid]] with [[hypnotic]] and [[sedative]] effects. It is found naturally in a variety of Australian and African plants including ''[[Evodia xanthoxyloides]]''<ref>{{cite journal | doi = 10.1071/CH9540087 | last1 = Eastwood | first1 = FW | last2 = Hughes | first2 = GK | last3 = Ritchie | first3 = E. | year = 1954 | title = Alkaloids of the Australian Rutaceae: Evodia xanthoxyloides F.Muell. IV. The structures of Evoxine and Evoxoidine | url = | journal = Australian Journal of Chemistry | volume = 7 | issue = 1| pages = 87–98 }}</ref> and ''[[Teclea gerrardii]]''.<ref>{{cite journal | last1 = Waffo | first1 = AF | last2 = Coombes | first2 = PH | last3 = Crouch | first3 = NR | last4 = Mulholland | first4 = DA | last5 = El Amin | first5 = SM | last6 = Smith | first6 = PJ | title = Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa. | journal = Phytochemistry | volume = 68 | issue = 5 | pages = 663–7 | year = 2007 | pmid = 17174364 | doi = 10.1016/j.phytochem.2006.10.011 }}</ref>
'''Evoxine''' ('''haploperine''') is a [[furoquinoline alkaloid]] with [[hypnotic]] and [[sedative]] effects. It is found naturally in a variety of Australian and African plants including ''[[Evodia xanthoxyloides]]''<ref>{{cite journal | doi = 10.1071/CH9540087 | last1 = Eastwood | first1 = FW | last2 = Hughes | first2 = GK | last3 = Ritchie | first3 = E. | year = 1954 | title = Alkaloids of the Australian Rutaceae: Evodia xanthoxyloides F.Muell. IV. The structures of Evoxine and Evoxoidine | journal = Australian Journal of Chemistry | volume = 7 | issue = 1| pages = 87–98 }}</ref> and ''[[Teclea gerrardii]]''.<ref>{{cite journal | last1 = Waffo | first1 = AF | last2 = Coombes | first2 = PH | last3 = Crouch | first3 = NR | last4 = Mulholland | first4 = DA | last5 = El Amin | first5 = SM | last6 = Smith | first6 = PJ | title = Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa. | journal = Phytochemistry | volume = 68 | issue = 5 | pages = 663–7 | year = 2007 | pmid = 17174364 | doi = 10.1016/j.phytochem.2006.10.011 | bibcode = 2007PChem..68..663K }}</ref>


==References==
==References==
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[[Category:Hypnotics]]
[[Category:Hypnotics]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
[[Category:Diols]]
[[Category:Vicinal diols]]
[[Category:Furans]]
[[Category:Oxygen heterocycles]]
[[Category:Quinolines]]
[[Category:Quinoline alkaloids]]
[[Category:Alkaloids]]
[[Category:Heterocyclic compounds with 3 rings]]




Latest revision as of 14:02, 21 January 2024

Evoxine
Names
IUPAC name
(±)-1-(4,8-Dimethoxyfuro[2,3-b]quinolin-7-yl)oxy-3-methylbutane-2,3-diol
Other names
Haploperine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYSA-N
  • InChI=1/C18H21NO6/c1-18(2,21)13(20)9-25-12-6-5-10-14(16(12)23-4)19-17-11(7-8-24-17)15(10)22-3/h5-8,13,20-21H,9H2,1-4H3
    Key: FGANMDNHTVJAHL-UHFFFAOYAV
  • CC(C)(C(COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC)O)O
Properties
C18H21NO6
Molar mass 347.367 g·mol−1
Pharmacology
none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Evoxine (haploperine) is a furoquinoline alkaloid with hypnotic and sedative effects. It is found naturally in a variety of Australian and African plants including Evodia xanthoxyloides[1] and Teclea gerrardii.[2]

References

[edit]
  1. ^ Eastwood, FW; Hughes, GK; Ritchie, E. (1954). "Alkaloids of the Australian Rutaceae: Evodia xanthoxyloides F.Muell. IV. The structures of Evoxine and Evoxoidine". Australian Journal of Chemistry. 7 (1): 87–98. doi:10.1071/CH9540087.
  2. ^ Waffo, AF; Coombes, PH; Crouch, NR; Mulholland, DA; El Amin, SM; Smith, PJ (2007). "Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa". Phytochemistry. 68 (5): 663–7. Bibcode:2007PChem..68..663K. doi:10.1016/j.phytochem.2006.10.011. PMID 17174364.


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