Tebain
IUPAC ime
6,7,8,14-tetradehydro-4,5a-epoxy- 3,6-dimethoxy-17-methylmorphinan
Drugi nazivi
Paramorfin
Identifikacija
CAS registarski broj
115-37-7 Y
PubChem [ 1] [ 2]
5324289
ChemSpider [ 3]
4481822 Y , 4479543
UNII
2P9MKG8GX7 Y
KEGG [ 4]
C06173
MeSH
Tebain
ChEBI
9519
ChEMBL [ 5]
CHEMBL403893 Y
Jmol -3D slike
Slika 1
O(c5ccc4c2c5O[C@H]3C(/OC)=C\C=C1\[C@H](N(CC[C@]123)C)C4)C
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
Svojstva
Molekulska formula
C19 H21 NO3
Molarna masa
311.37 g mol−1
Farmakologija
Metabolizam
O -demetilacija[ 6]
Legalni status
Class A (UK )
Schedule II (SAD )
Y (šta je ovo?)
(verifikuj)
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
Infobox references
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 .
↑ 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 .