Laudanosine | CAS#1699-51-0 | metabolite

MedKoo Cat#: 598438 | Name: Laudanosine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Laudanosine is a recognized metabolite 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.

Chemical Structure

Laudanosine

CAS#1699-51-0

Theoretical Analysis

MedKoo Cat#: 598438

Name: Laudanosine

CAS#: 1699-51-0

Chemical Formula: C21H27NO4

Exact Mass: 357.1940

Molecular Weight: 357.45

Elemental Analysis: C, 70.56; H, 7.61; N, 3.92; O, 17.90

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00	2 Weeks

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Related CAS #

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Synonym

Laudanosine; AI3-61890; AI3 61890; AI361890; NSC 94267; NSC-94267; NS 94267;

IUPAC/Chemical Name

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

InChi Key

KGPAYJZAMGEDIQ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

COC1=CC(CC2N(C)CCC3=C2C=C(OC)C(OC)=C3)=CC=C1OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DL-Laudanosine, an Atracurium and Cisatracurium metabolite, crosses the blood–brain barrier and may cause excitement and seizure activity.

In vitro activity:

However, laudanosine displayed an inhibitory effect at the low-affinity GABA receptors labeled by [3H]bicuculline methochloride, with an IC50 value of 10 microM. At the opioid receptor subtype, laudanosine lowered radiolabeled opioid binding at the mu 1, mu 2, delta, kappa 1, and kappa 3 receptors with Ki values of 2.7, 13, 5.5, 21, and 24 microM, respectively, concentrations seen clinically in blood and approaching those measured in cerebrospinal fluid. Reference: Brain Res. 1994 May 23;646(2):235-41. https://pubmed.ncbi.nlm.nih.gov/8069669/

In vivo activity:

In Xenopus Oocytes expressing nicotinic acetylcholine receptors (nAChRs), laudanosine has activating and inhibiting effects on nAChRs depending on its concentration. Reference: Adv Exp Med Biol. 2010;669:177-80. https://pubmed.ncbi.nlm.nih.gov/20217344/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	279.76

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 357.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M. Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity. Brain Res. 1994 May 23;646(2):235-41. doi: 10.1016/0006-8993(94)90084-1. PMID: 8069669. 2. Sakuraba S, Hosokawa Y, Kaku Y, Takeda J, Kuwana S. Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats. Adv Exp Med Biol. 2010;669:177-80. doi: 10.1007/978-1-4419-5692-7_35. PMID: 20217344. 3. Chuliá S, Ivorra MD, Lugnier C, Vila E, Noguera MA, D'Ocon P. Mechanism of the cardiovascular activity of laudanosine: comparison with papaverine and other benzylisoquinolines. Br J Pharmacol. 1994 Dec;113(4):1377-85. doi: 10.1111/j.1476-5381.1994.tb17150.x. PMID: 7889295; PMCID: PMC1510478.

In vitro protocol:

In vivo protocol:

1. Sakuraba S, Hosokawa Y, Kaku Y, Takeda J, Kuwana S. Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats. Adv Exp Med Biol. 2010;669:177-80. doi: 10.1007/978-1-4419-5692-7_35. PMID: 20217344. 2. Chuliá S, Ivorra MD, Lugnier C, Vila E, Noguera MA, D'Ocon P. Mechanism of the cardiovascular activity of laudanosine: comparison with papaverine and other benzylisoquinolines. Br J Pharmacol. 1994 Dec;113(4):1377-85. doi: 10.1111/j.1476-5381.1994.tb17150.x. PMID: 7889295; PMCID: PMC1510478.

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