Tebain (paramorfin) je opijatni alkaloid. Njegovi ime potiče od grč. Θῆβαι - Teba, drevni grad u gornjem Egiptu. Manjinski konstituent opijuma, tebain je hemijski sličan morfinu i kodeinu, ali ima stimulatorne umesto depresantskih efekata. On izaziva konvulzije slično strihninskom trovanju u većim dozama. Međutim veštački enantiomer (+)-tebain pokazuje analgetičko dejstvo, koje je posredovano putem opioidnih receptora.[8] Tebain nema terapeutsku primenu, ali kao glavni alkaloid ekstrahovan iz Papaver bracteatum, on se konvertovuje u niz jedinjenja: oksikodon, oksimorfon, nalbufin, nalokson, naltrekson, buprenorfin i etorfin.
Tebain
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IUPAC ime
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6,7,8,14-tetradehydro-4,5a-epoxy- 3,6-dimethoxy-17-methylmorphinan |
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Drugi nazivi
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Paramorfin
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Identifikacija
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CAS registarski broj
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115-37-7 Y |
PubChem[1][2] |
5324289
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ChemSpider[3] |
4481822 Y, 4479543
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UNII
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2P9MKG8GX7 Y |
KEGG[4] |
C06173
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MeSH
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Tebain
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ChEBI
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9519
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ChEMBL[5] |
CHEMBL403893 Y |
Jmol-3D slike
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Slika 1
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O(c5ccc4c2c5O[C@H]3C(/OC)=C\C=C1\[C@H](N(CC[C@]123)C)C4)C |
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InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1 Y Kod: FQXXSQDCDRQNQE-VMDGZTHMSA-N Y |
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Svojstva
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Molekulska formula
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C19H21NO3 |
Molarna masa
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311.37 g mol−1 |
Farmakologija
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Metabolizam
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O-demetilacija[6] |
Legalni status
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Class A(UK)
Schedule II(SAD)
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Y (šta je ovo?)
(verifikuj)
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
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Infobox references
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Literatura
uredi
- ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
- ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
- ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
- ↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
- ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
- ↑ Mikus G, Somogyi AA, Bochner F, Eichelbaum M. (1991). „Thebaine O-demethylation to oripavine: genetic differences between two rat strains”. Xenobiotica 21 issue=11: 1501-9. PMID 1763524.
- ↑ WHO Advisory Group. (1980). „The dependence potential of thebaine”. Bulletin on Narcotics 32 (1): 45–54. PMID 6778542. Arhivirano iz originala na datum 2005-05-29. Pristupljeno 2014-04-11.
- ↑ Aceto MD, Harris LS, Abood ME, Rice KC (1999-01-22). „Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine”. European Journal of Pharmacology 365 ((2-3)): 143-7. PMID 9988096.