Laudanosine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424953216

| ImageFile = Laudanosine.svg

| ImageSize = 220

| ImageName = Skeletal formula

| ImageFile1 = Laudanosine molecule spacefill.png

| ImageSize1 = 180

| ImageName1 = Space-filling model

| PIN = (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

| OtherNames = N-Methyl-1,2,3,4-tetrahydropapaverine

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 2688-77-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = DA7R5WVN48

| PubChem = 73397

| EINECS = 220-253-2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 66114

| 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 }}

|Section2={{Chembox Properties

| C=21 | H=27 | N=1 | O=4

| Appearance =

| Density =

| MeltingPtC = 89

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

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Laudanosine or N-methyltetrahydropapaverine is a recognized metabolite{{cite journal |vauthors=Fodale V, Santamaria LB |title=Laudanosine, an atracurium and cisatracurium metabolite |journal=Eur J Anaesthesiol |volume=19 |issue=7 |pages=466–73 |date=July 2002 |pmid=12113608 |doi=10.1017/s0265021502000777|doi-broken-date=1 November 2024 }} 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.

Image:Opium pod cut to demonstrate fluid extraction1.jpg

Laudanosine also occurs naturally in minute amounts (0.1%) in opium, from which it was first isolated in 1871.{{cite book |chapter-url=https://books.google.com/books?id=KxTKLlac60wC&q=laudanosine&pg=PA55 |chapter=The Benzylisoquinoline Alkaloids |author=Burger A |title=The Alkaloids: Chemistry and Physiology |orig-year=1954 |year=2005 |volume=4 |veditors=Manske RH, Holmes HL |pages=48 |location=New York |publisher=Academic Press |isbn=0-12-469504-3}} Retrieved September 18, 2008 through Google Book Search. Partial dehydrogenation of laudanosine will lead to papaverine, the alkaloid found in the opium poppy plant (Papaver somniferum).

Laudanosine is a benzyltetrahydroisoquinoline alkaloid. It has been shown to interact with GABA receptors, glycine receptors, opioid receptors, and nicotinic acetylcholine receptors,{{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 }}{{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 }} but not benzodiazepine or muscarinic receptors, which are also involved in epilepsy and other types of seizures.{{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 }}