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Laudanosine

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Laudanosine
Names
Skeletal formula
Space-filling model
Preferred IUPAC name (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Other names N-Methyl-1,2,3,4-tetrahydropapaverine
Identifiers
CAS Number	2688-77-9^Y
3D model (JSmol)	Interactive image
ChemSpider	66114^N
ECHA InfoCard	100.018.412
EC Number	220-253-2
PubChem CID	73397
UNII	DA7R5WVN48^Y
CompTox Dashboard(EPA)	DTXSID30878577
InChI InChI=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^N Key: KGPAYJZAMGEDIQ-KRWDZBQOSA-N^N 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 Key: KGPAYJZAMGEDIQ-KRWDZBQOBO
SMILES CN1CCc2cc(c(cc2[C@@H]1Cc3ccc(c(c3)OC)OC)OC)OC
Properties
Chemical formula	C₂₁H₂₇NO₄
Molar mass	357.450 g·mol⁻¹
Melting point	89 °C (192 °F; 362 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Laudanosine orN-methyltetrahydropapaverine is a recognized metabolite^[1] ofatracurium andcisatracurium. 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 ofcisatracurium oratracurium.

Capsule ofPapaver 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%) inopium, from which it was first isolated in 1871.^[2] Partialdehydrogenation of laudanosine will lead topapaverine, the alkaloid found in the opium poppy plant (Papaver somniferum).

Laudanosine is abenzyltetrahydroisoquinoline alkaloid. It has been shown to interact withGABA receptors,glycine receptors,opioid receptors, andnicotinic acetylcholine receptors,^[1]^[3]^[4] but notbenzodiazepine ormuscarinic receptors, which are also involved in epilepsy and other types of seizures.^[5]

References

[edit]

^^a ^bFodale V, Santamaria LB (July 2002). "Laudanosine, an atracurium and cisatracurium metabolite".Eur J Anaesthesiol.19 (7):466–73.doi:10.1017/s0265021502000777.PMID 12113608.
^Burger A (2005) [1954]."The Benzylisoquinoline Alkaloids". In Manske RH, Holmes HL (eds.).The Alkaloids: Chemistry and Physiology. Vol. 4. New York: Academic Press. p. 48.ISBN 0-12-469504-3. Retrieved September 18, 2008 throughGoogle Book Search.
^Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M (May 1994). "Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity".Brain Res.646 (2):235–241.doi:10.1016/0006-8993(94)90084-1.PMID 8069669.S2CID 35031924.
^Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I (Sep 2005)."Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors".Br J Pharmacol.146 (1):15–24.doi:10.1038/sj.bjp.0706307.PMC 1576253.PMID 15980871.
^Katz Y, Gavish M (Jan 1989). "Laudanosine does not displace receptor-specific ligands from the benzodiazepinergic or muscarinic receptors".Anesthesiology.70 (1):109–111.doi:10.1097/00000542-198901000-00020.PMID 2536252.

Pharmacodynamics

GABA receptor modulators

Ionotropic

GABA_ATooltip γ-Aminobutyric acid A receptor

Agonists:4-AHP
(+)-Catechin
Bamaluzole
Barbiturates (e.g.,phenobarbital)
Beta-Alanine
BL-1020
DAVA
DH-P4S
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
IAA (IMA)
Ibotenic acid
iso-THAZ
Isoguvacine
Isonipecotic acid
Kojic amine
L-838,417
Lignans (e.g.,honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g.,allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
4-PIOL
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g.,borneol)
Thio-4-PIOL
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; seehere for a full list):α-EMTBL
Alcohols (e.g.,drinking alcohol,2M2B)
Anabolic steroids
Avermectins (e.g.,ivermectin)
Barbiturates (e.g.,phenobarbital)
Benzodiazepines (e.g.,diazepam)
Bromide compounds (e.g.,potassium bromide)
Carbamates (e.g.,meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g.,mefenamic acid)
Flavonoids (e.g.,apigenin,hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g.,etomidate)
Kava constituents (e.g.,kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,allopregnanolone,cholesterol,THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil),cyclopyrrolones (e.g.,zopiclone),imidazopyridines (e.g.,zolpidem),pyrazolopyrimidines (e.g.,zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g.,propofol)
Phenytoin
Piperidinediones (e.g.,glutethimide)
Propanidid
Pyrazolopyridines (e.g.,etazolate)
Quinazolinones (e.g.,methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,baicalin)
Stiripentol
Sulfonylalkanes (e.g.,sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g.,valerenic acid)
Volatiles/gases (e.g.,chloral hydrate,chloroform,diethyl ether,paraldehyde,sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators:5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin,picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

Metabotropic

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

Glycine receptor modulators

Receptor
(ligands)

GlyRTooltip Glycine receptor

Positive modulators:Alcohols (e.g.,brometone,chlorobutanol (chloretone),ethanol (alcohol),tert-butanol (2M2P),tribromoethanol,trichloroethanol,trifluoroethanol)
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g.,pentobarbital,sodium thiopental)
Chlormethiazole
D12-116
Dihydropyridines (e.g.,nicardipine)
Etomidate
Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g.,alfaxolone,pregnenolone (eltanolone),pregnenolone acetate,minaxolone,ORG-20599)
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g.,atropine,bemesetron,cocaine,LY-278584,tropisetron,zatosetron)
Volatiles/gases (e.g.,chloral hydrate,chloroform,desflurane,diethyl ether (ether),enflurane,halothane,isoflurane,methoxyflurane,sevoflurane,toluene,trichloroethane (methyl chloroform),trichloroethylene)
Xenon
Zinc

Negative modulators:Amiloride
Benzodiazepines (e.g.,bromazepam,clonazepam,diazepam,flunitrazepam,flurazepam)
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g.,nicardipine,nifedipine,nitrendipine)
Furosemide
Genistein
Ginkgo constituents (e.g.,bilobalide,ginkgolides (e.g.,ginkgolide A,ginkgolide B,ginkgolide C,ginkgolide J,ginkgolide M))
Imipramine
NBQX
Neuroactive steroids (e.g.,3α-androsterone sulfate,3β-androsterone sulfate,deoxycorticosterone,DHEA sulfate,pregnenolone sulfate,progesterone)
Opioids (e.g.,codeine,dextromethorphan,dextrorphan,levomethadone,levorphanol,morphine,oripavine,pethidine,thebaine)
Picrotoxin (i.e.,picrotin andpicrotoxinin)
PMBA
Riluzole
Tropeines (e.g.,bemesetron,LY-278584,tropisetron,zatosetron)
Verapamil
Zinc

NMDARTooltip N-Methyl-D-aspartate receptor

Seehere instead.

Transporter
(blockers)

GlyT1Tooltip Glycine transporter 1	ACPPB ALX-5407 (NFPS) ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol (alcohol) Glycyldodecylamide GSK1018921 Iclepertin LY-2365109 Mardepodect ORG-24598 ORG-25935 (SCH-900435) Pesampator (BIIB-104, PF-04958242) PF-03463275 Sarcosine SNG-12 (Synapsinae) SSR-103,800 SSR-504,734 Tilapertin
GlyT2Tooltip Glycine transporter 2	ALX-1393 Amoxapine Ethanol (alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368

See also: Receptor/signaling modulators; GABA receptor modulators; GABA_A receptor positive modulators; Ionotropic glutamate receptor modulators

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

Precursors
(andprodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

Opioid receptor modulators

μ-opioid
(MOR)

Agonists
(abridged;
full list)

Antagonists

δ-opioid
(DOR)

Agonists

Antagonists

κ-opioid
(KOR)

Agonists

Antagonists

Nociceptin
(NOP)

Agonists

Antagonists

Others

Propeptides:β-Lipotropin (proendorphin)
Prodynorphin
Proenkephalin
Pronociceptin
Proopiomelanocortin (POMC)

Others:Kyotorphin (met-enkephalin releaser/degradation stabilizer)

v t e Opium components
Alkaloids	16-Hydroxythebaine Berberine Canadine Codamine Coptisine Coreximine Cycloartenone Cyclolaudenol Dehydroreticuline Dihydrosanguinarine Glaucine Isoboldine Isocorypalmine Laudanidine Magnoflorine Narceine Narceinone Norlaudanosoline Norsanguinarine Oripavine Oxysanguinarine Palaudine Papaverrubine B (O-methyl-porphyroxine) Papaverrubine C (epiporphyroxine) Reticuline Salutaridine (sinoacutine) Sanguinarine Scoulerine Somniferine Stepholidine
Morphine group (Phenanthrenes. Includesopioids)	Codeine Morphine Narcotoline Neopine Perparin Papaverrubine D (porphyroxine) Pseudocodeine Pseudomorphine Thebaine
Isoquinolines	Cotarnine Eupaverine Hydrocotarnine Laudanosine Laudanine Noscapine (narcotine) Papaverine Papaveraldine Xanthaline
Protopine group	α-Allocryptopine Corycavamine Corycavine Cryptopine Protopine
Tetrahydroprotoberberine group	Corydaline Corybulbine Isocorybulbine Capaurine
Aporphine group	Dicentrine Glaucine Corytuberine Cularine Corydine Isocorydine Bulbocapnine
Phtalide-isoquinolines	Adulmine Bicuculline Bicucine Corlumine
α-Naphthaphenanthridines	Chelidonine β-Homochelidonoine Chelerythrine Sanguinarine
Other components	Meconic acid Cycloartenol

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