MedKoo Cat#: 146104 | Name: Illudinine

Description:

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

Illudinine is a bioactive compound derived from the Omphalotus genus of fungi, particularly the jack-o'-lantern mushroom (Omphalotus olearius). It has shown potential in the field of cancer research due to its cytotoxic properties, particularly against various tumor cell lines. Illudinine functions by interfering with cellular processes, including DNA replication and cell division, leading to the death of cancerous cells. Its mechanism involves the formation of highly reactive oxygen species (ROS) that damage cellular components, ultimately inducing apoptosis in target cells.

Chemical Structure

Illudinine
Illudinine
CAS#18500-63-5

Theoretical Analysis

MedKoo Cat#: 146104

Name: Illudinine

CAS#: 18500-63-5

Chemical Formula: C16H17NO3

Exact Mass: 271.1208

Molecular Weight: 271.32

Elemental Analysis: C, 70.83; H, 6.32; N, 5.16; O, 17.69

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
Illudinine; NSC-135050; NSC135050; NSC 135050;
IUPAC/Chemical Name
9-methoxy-7,7-dimethyl-7,8-dihydro-6H-cyclopenta[g]isoquinoline-5-carboxylic acid
InChi Key
FSBVQCVHOXXMGN-UHFFFAOYSA-N
InChi Code
1S/C16H17NO3/c1-16(2)6-10-11(7-16)14(20-3)12-8-17-5-4-9(12)13(10)15(18)19/h4-5,8H,6-7H2,1-3H3,(H,18,19)
SMILES Code
COC1=C2CC(C)(C)CC2=C(C(O)=O)C3=CC=NC=C13
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 271.32 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: Morrison AE, Hoang TT, Birepinte M, Dudley GB. Synthesis of Illudinine from Dimedone. Org Lett. 2017 Feb 17;19(4):858-861. doi: 10.1021/acs.orglett.6b03887. Epub 2017 Jan 30. PMID: 28133968. 2: Gaston R Jr, Geldenhuys WJ, Dudley GB. Synthesis of Illudinine from Dimedone and Identification of Activity as a Monoamine Oxidase Inhibitor. J Org Chem. 2020 Nov 6;85(21):13429-13437. doi: 10.1021/acs.joc.0c01301. Epub 2020 Aug 27. PMID: 32830978. 3: Nair MS, Takeshita H, McMorris TC, Anchel M. Metabolites of Clitocybe illudens. IV. Illudalic acid, a sesquiterpenoid, and illudinine, a sesquiterpenoid alkaloid. J Org Chem. 1969 Jan;34(1):240-3. doi: 10.1021/jo00838a058. PMID: 5768225. 4: Teske JA, Deiters A. Microwave-mediated nickel-catalyzed cyclotrimerization reactions: total synthesis of illudinine. J Org Chem. 2008 Jan 4;73(1):342-5. doi: 10.1021/jo7020955. Epub 2007 Dec 5. PMID: 18052296. 5: Duangkamol C, Batsomboon P, Stiegman AE, Dudley GB. Microwave Heating Outperforms Conventional Heating for a Thermal Reaction that Produces a Thermally Labile Product: Observations Consistent with Selective Microwave Heating. Chem Asian J. 2019 Aug 1;14(15):2594-2597. doi: 10.1002/asia.201900625. Epub 2019 Jun 26. PMID: 31157510.