MedKoo Cat#: 146092 | Name: Paspalinine

Description:

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

Paspalinine is a naturally occurring alkaloid with notable bioactive properties, particularly in its ability to modulate neurotransmitter systems. It primarily works by interacting with dopamine and serotonin receptors, which can influence mood regulation, cognitive function, and motor control. Paspalinine shows potential in the treatment of neurological disorders such as Parkinson's disease and depression, by enhancing dopaminergic activity and supporting neuroprotection.

Chemical Structure

Paspalinine
Paspalinine
CAS#63722-91-8

Theoretical Analysis

MedKoo Cat#: 146092

Name: Paspalinine

CAS#: 63722-91-8

Chemical Formula: C27H31NO4

Exact Mass: 433.2253

Molecular Weight: 433.55

Elemental Analysis: C, 74.80; H, 7.21; N, 3.23; O, 14.76

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
Paspalinine; Paspalinin;
IUPAC/Chemical Name
(3R,5bS,7aS,13bS,13cR,15aS)-5b-hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4H-3,15a-epoxyoxepino[2'',3'':5',6']benzo[1',2':6,7]indeno[1,2-b]indol-4-one
InChi Key
BPTIXFRJAOKMRK-SAMRHTEJSA-N
InChi Code
1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3/t15-,22-,24+,25+,26+,27-/m0/s1
SMILES Code
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]5(C)CC[C@@]67O[C@@H](C(=O)C=C6[C@]5(O)CC2)C(C)(C)O7
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 433.55 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: Guo LD, Xu Z, Tong R. Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene. Angew Chem Int Ed Engl. 2022 Jan 17;61(3):e202115384. doi: 10.1002/anie.202115384. Epub 2021 Nov 27. PMID: 34784090. 2: Li W, Yi G, Lin K, Chen G, Hui Y, Chen W. Cytotoxic Indole Diterpenoids from a Sphagneticola trilobata-Derived Fungus Aspergillus sp. PQJ-1. Molecules. 2023 Oct 10;28(20):7003. doi: 10.3390/molecules28207003. PMID: 37894482; PMCID: PMC10609460. 3: Steyn PS, Vleggaar R. Tremorgenic mycotoxins. Fortschr Chem Org Naturst. 1985;48:1-80. doi: 10.1007/978-3-7091-8815-6_1. PMID: 3912307. 4: Enomoto M, Morita A, Kuwahara S. Total synthesis of the tremorgenic indole diterpene paspalinine. Angew Chem Int Ed Engl. 2012 Dec 14;51(51):12833-6. doi: 10.1002/anie.201206299. Epub 2012 Nov 7. PMID: 23135880. 5: Enomoto M. Recent advances in the total syntheses of indole diterpenoids. Biosci Biotechnol Biochem. 2021 Jan 7;85(1):13-23. doi: 10.1093/bbb/zbaa061. PMID: 33577667. 6: Gilchrist CLM, Lacey HJ, Vuong D, Pitt JI, Lange L, Lacey E, Pilgaard B, Chooi YH, Piggott AM. Comprehensive chemotaxonomic and genomic profiling of a biosynthetically talented Australian fungus, Aspergillus burnettii sp. nov. Fungal Genet Biol. 2020 Oct;143:103435. doi: 10.1016/j.fgb.2020.103435. Epub 2020 Jul 20. PMID: 32702474. 7: Kozák L, Szilágyi Z, Tóth L, Pócsi I, Molnár I. Functional characterization of the idtF and idtP genes in the Claviceps paspali indole diterpene biosynthetic gene cluster. Folia Microbiol (Praha). 2020 Jun;65(3):605-613. doi: 10.1007/s12223-020-00777-6. Epub 2020 Feb 19. PMID: 32077051; PMCID: PMC7244603. 8: Gant DB, Cole RJ, Valdes JJ, Eldefrawi ME, Eldefrawi AT. Action of tremorgenic mycotoxins on GABAA receptor. Life Sci. 1987 Nov 9;41(19):2207-14. doi: 10.1016/0024-3205(87)90517-0. PMID: 2444852. 9: Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W. Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014 Jun 30;12(7):3970-81. doi: 10.3390/md12073970. PMID: 24983640; PMCID: PMC4113809. 10: Knaus HG, McManus OB, Lee SH, Schmalhofer WA, Garcia-Calvo M, Helms LM, Sanchez M, Giangiacomo K, Reuben JP, Smith AB 3rd, et al. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels. Biochemistry. 1994 May 17;33(19):5819-28. doi: 10.1021/bi00185a021. PMID: 7514038. 11: Andersen B, Frisvad JC. Natural occurrence of fungi and fungal metabolites in moldy tomatoes. J Agric Food Chem. 2004 Dec 15;52(25):7507-13. doi: 10.1021/jf048727k. PMID: 15675796. 12: Nicholson MJ, Koulman A, Monahan BJ, Pritchard BL, Payne GA, Scott B. Identification of two aflatrem biosynthesis gene loci in Aspergillus flavus and metabolic engineering of Penicillium paxilli to elucidate their function. Appl Environ Microbiol. 2009 Dec;75(23):7469-81. doi: 10.1128/AEM.02146-08. Epub 2009 Oct 2. PMID: 19801473; PMCID: PMC2786402. 13: Uhlig S, Egge-Jacobsen W, Vrålstad T, Miles CO. Indole-diterpenoid profiles of Claviceps paspali and Claviceps purpurea from high-resolution Fourier transform Orbitrap mass spectrometry. Rapid Commun Mass Spectrom. 2014 Jul 30;28(14):1621-34. doi: 10.1002/rcm.6938. PMID: 24895259.