MedKoo Cat#: 597406 | Name: Laudanidine

Description:

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

Laudanidine is a nitrile-stabilized ammonium ylide.

Chemical Structure

Laudanidine
Laudanidine
CAS#301-21-3

Theoretical Analysis

MedKoo Cat#: 597406

Name: Laudanidine

CAS#: 301-21-3

Chemical Formula: C20H25NO4

Exact Mass: 343.1784

Molecular Weight: 343.42

Elemental Analysis: C, 69.95; H, 7.34; N, 4.08; O, 18.63

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Laudanidine; Tritopin; Tritopine; L-Laudanine;
IUPAC/Chemical Name
(R)-5-((6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2-methoxyphenol
InChi Key
MPYHGNAJOKCMAQ-MRXNPFEDSA-N
InChi Code
InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3/t16-/m1/s1
SMILES Code
OC1=CC(C[C@H]2N(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

Preparing Stock Solutions

The following data is based on the product molecular weight 343.42 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.

Recalculate based on batch purity %
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
1: Orejarena Pacheco JC, Lahm G, Opatz T. Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine. J Org Chem. 2013 May 17;78(10):4985-92. doi: 10.1021/jo400659n. Epub 2013 May 9. PubMed PMID: 23634947. 2: Blank N, Opatz T. Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile. J Org Chem. 2011 Dec 2;76(23):9777-84. doi: 10.1021/jo201871c. Epub 2011 Oct 26. PubMed PMID: 22004161. 3: Blanchfield JT, Sands DP, Kennard CH, Byriel KA, Kitching W. Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species. Phytochemistry. 2003 Jul;63(6):711-20. PubMed PMID: 12842145. 4: Kanokmedhakul S, Kanokmedhakul K, Lekphrom R. Bioactive constituents of the roots of Polyalthia cerasoides. J Nat Prod. 2007 Sep;70(9):1536-8. Epub 2007 Sep 11. PubMed PMID: 17845001. 5: Lurie IS, Toske SG. Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling. J Chromatogr A. 2008 Apr 25;1188(2):322-6. doi: 10.1016/j.chroma.2008.03.011. Epub 2008 Mar 18. PubMed PMID: 18374345.