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more corrections to the erroneous description of laudanosine |
correct IUPAC name |
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424953216
| ImageFile = Laudanosine.svg
| ImageSize = 220
| ImageName = Skeletal formula
| IUPACName = (1''S'')-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy- 2-methyl-3,4-dihydro-1''H''-isoquinoline▼
| ImageFile1 = Laudanosine molecule spacefill.png
| ImageSize1 = 180
| ImageName1 = Space-filling model
▲|
| OtherNames = ''N''-Methyl-1,2,3,4-tetrahydropapaverine
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2688-77-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DA7R5WVN48
| PubChem = 73397
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| Section2 = {{Chembox Properties▼
| ChemSpiderID = 66114
| C=21 |H=27 |N=1 |O=4▼
| SMILES = CN1CCc2cc(c(cc2[C@@H]1Cc3ccc(c(c3)OC)OC)OC)OC
| InChI = 1/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
| InChIKey = KGPAYJZAMGEDIQ-KRWDZBQOBO
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KGPAYJZAMGEDIQ-KRWDZBQOSA-N }}
▲| C=21 | H=27 | N=1 | O=4
| Appearance =
| Density =
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| BoilingPt =
| Solubility = }}
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| MainHazards =
| FlashPt =
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}}
}}
'''Laudanosine''' or '''''N''-methyltetrahydropapaverine''' is a recognized metabolite<ref name=Fodale>{{cite journal |author=Fodale V, Santamaria LB |title=Laudanosine, an atracurium and cisatracurium metabolite |journal=Eur J Anaesthesiol |volume=19 |issue=7 |pages=466–73 |year=2002 |month=July |pmid=12113608}}</ref> of [[atracurium]] and [[cisatracurium]]. Laudanosine decreases the seizure threshold, and thus it can induce seizures if present at sufficient threshold concentrations; however such concentrations are unlikely to be produced consequent to chemodegradable metabolism of clinically administered doses of [[cisatracurium]] or [[atracurium]]. ▼
▲'''Laudanosine''' or '''''N''-methyltetrahydropapaverine''' is a recognized metabolite<ref name=Fodale>{{cite journal |
Laudanosine also occurs naturally in minute amounts (0.1%) in [[opium]], from which it was first isolated in 1871.<ref>{{cite book |chapterurl=http://books.google.com/books?id=KxTKLlac60wC&pg=PA55&dq=laudanosine&sig=ACfU3U2OZxmvO0Pl8Jnp8KuGXHzMllcnQA#PPA48,M1 |chapter=The Benzylisoquinoline Alkaloids |author=Burger A |title=The Alkaloids: Chemistry and Physiology |origyear=1954 |year=2005 |volume=4 |editor=Manske RHF, Holmes HL (eds.) |pages=p. 48 |location=New York |publisher=Academic Press |isbn=0124695043}} Retrieved September 18, 2008 through [[Google Book Search]].</ref> Partial [[Dehydration reaction|dehydration]] of laudanosine will lead to [[papaverine]].▼
[[Image:Opium pod cut to demonstrate fluid extraction1.jpg|thumb|left|Capsule of ''Papaver somniferum'' showing latex (opium) exuding from incision. Laudanosine occurs naturally in small amounts (0.1%) in opium.]]
▲Laudanosine also occurs naturally in minute amounts (0.1%) in [[opium]], from which it was first isolated in 1871.<ref>{{cite book |
Laudanosine is a [[benzyltetrahydroisoquinoline]] [[alkaloid]]. It has been shown to interact with [[GABA receptor]]s, [[glycine receptor]]s, [[opioid receptor]]s, and [[nicotinic acetylcholine receptor]]s,<ref name=Fodale/><ref>{{cite journal |vauthors=Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M |title=Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity |journal= Brain Res |volume=646 |issue=2 |pages=235–241 |date=May 1994 |pmid=8069669 |doi=10.1016/0006-8993(94)90084-1 |s2cid=35031924 }}</ref><ref>{{cite journal |vauthors=Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I |title=Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors |journal= Br J Pharmacol |volume=146 |issue=1 |pages=15–24 |date=Sep 2005|pmid=15980871 |doi= 10.1038/sj.bjp.0706307 |pmc= 1576253 }}</ref> but not [[benzodiazepine receptor|benzodiazepine]] or [[muscarinic receptor]]s, which are also involved in epilepsy and other types of seizures.<ref>{{cite journal |vauthors=Katz Y, Gavish M |title= Laudanosine does not displace receptor-specific ligands from the benzodiazepinergic or muscarinic receptors |journal= Anesthesiology|volume=70|issue=1 |pages= 109–111 |date=Jan 1989 |pmid= 2536252 |doi= 10.1097/00000542-198901000-00020 }}</ref>
==References==
{{
{{Navboxes
[[Category:Isoquinolines]]▼
| title = [[Pharmacodynamics]]
| titlestyle = background:#ccccff
| list1 =
{{GABA receptor modulators}}
{{Glycine receptor modulators}}
{{Nicotinic acetylcholine receptor modulators}}
{{Opioid receptor modulators}}
}}
{{Components of Opium}}
[[Category:Natural opium alkaloids]]
[[Category:
[[Category:GABAA receptor negative allosteric modulators]]
[[Category:Glycine receptor antagonists]]
[[Category:Nicotinic antagonists]]
{{nervous-system-drug-stub}}
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