Paynantheine | CAS#4697-66-9 | alkaloid

MedKoo Cat#: 145358 | Name: Paynantheine

Description:

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

Paynantheine is an opioidergic kratom alkaloid. Paynantheine is more effective against MCF7MX and EPG85. Studies have shown that Paynantheine can reduce resistance in cancer patients. Paynantheine exhibits high affinity for 5-HT1ARs and 5-HT2BRs.

Chemical Structure

Paynantheine

CAS#4697-66-9

Theoretical Analysis

MedKoo Cat#: 145358

Name: Paynantheine

CAS#: 4697-66-9

Chemical Formula: C23H28N2O4

Exact Mass: 396.2049

Molecular Weight: 396.49

Elemental Analysis: C, 69.68; H, 7.12; N, 7.07; O, 16.14

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

Paynantheine;

IUPAC/Chemical Name

methyl (E)-3-methoxy-2-((2S,3R,12bS)-8-methoxy-3-vinyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acrylate

InChi Key

JGZKIGWXPPFMRG-CYSPOEIOSA-N

InChi Code

1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19-/m0/s1

SMILES Code

[H][C@@]12C[C@@H]([C@H](CN1CCC3=C2NC4=C3C(OC)=CC=C4)C=C)C(=C/OC)\C(=O)OC

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 396.49 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

1: Abdali N, Nadipour Borujeni M, Hosseini SA, Malekzadeh R, Abolhasani M, Mirzaei SA, Elahian F. Paynantheine more effectively reverses multidrug resistance in malignant EPG85.257RDB and MCF7MX cells than morphine and speciociliatine. Cell Biol Int. 2024 Jun;48(6):861-871. doi: 10.1002/cbin.12152. Epub 2024 Mar 13. PMID: 38480672. 2: Karunakaran T, Ganasan J, Rusmadi NN, Santhanam R, Mordi MN. In-vitro hepatotoxic activity of mitragynine and paynantheine isolated from the leaves of Mitragyna speciosa Korth. (Kratom). Nat Prod Res. 2024 Jul 9:1-5. doi: 10.1080/14786419.2024.2375760. Epub ahead of print. PMID: 38982630. 3: Gutridge AM, Chakraborty S, Varga BR, Rhoda ES, French AR, Blaine AT, Royer QH, Cui H, Yuan J, Cassell RJ, Szabó M, Majumdar S, van Rijn RM. Evaluation of Kratom Opioid Derivatives as Potential Treatment Option for Alcohol Use Disorder. Front Pharmacol. 2021 Nov 3;12:764885. doi: 10.3389/fphar.2021.764885. PMID: 34803709; PMCID: PMC8596301. 4: Philipp AA, Wissenbach DK, Weber AA, Zapp J, Maurer HH. Metabolism studies of the Kratom alkaloids mitraciliatine and isopaynantheine, diastereomers of the main alkaloids mitragynine and paynantheine, in rat and human urine using liquid chromatography-linear ion trap-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 May 1;879(15-16):1049-55. doi: 10.1016/j.jchromb.2011.03.005. Epub 2011 Mar 29. PMID: 21450536. 5: León F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londoño C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR. Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors. J Med Chem. 2021 Sep 23;64(18):13510-13523. doi: 10.1021/acs.jmedchem.1c00726. Epub 2021 Sep 1. PMID: 34467758; PMCID: PMC9235362. 6: Kerschgens IP, Claveau E, Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction. Chem Commun (Camb). 2012 Dec 28;48(100):12243-5. doi: 10.1039/c2cc37023a. PMID: 23150886. 7: Philipp AA, Wissenbach DK, Weber AA, Zapp J, Zoerntlein SW, Kanogsunthornrat J, Maurer HH. Use of liquid chromatography coupled to low- and high-resolution linear ion trap mass spectrometry for studying the metabolism of paynantheine, an alkaloid of the herbal drug Kratom in rat and human urine. Anal Bioanal Chem. 2010 Apr;396(7):2379-91. doi: 10.1007/s00216-009-3239-1. Epub 2009 Nov 10. PMID: 19902190. 8: Basiliere S, Kerrigan S. Temperature and pH-Dependent Stability of Mitragyna Alkaloids. J Anal Toxicol. 2020 May 18;44(4):314-324. doi: 10.1093/jat/bkz103. PMID: 31897484. 9: Basiliere S, Bryand K, Kerrigan S. Identification of five Mitragyna alkaloids in urine using liquid chromatography-quadrupole/time of flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Mar 30;1080:11-19. doi: 10.1016/j.jchromb.2018.02.010. Epub 2018 Feb 13. PMID: 29459087. 10: Melchert PW, Zhang Q, Mukhopadhyay S, Kanumuri SRR, McCurdy CR, Markowitz JS. An in vitro evaluation of kratom (Mitragyna speciosa) on the catalytic activity of carboxylesterase 1 (CES1). Chem Biol Interact. 2023 Oct 1;384:110715. doi: 10.1016/j.cbi.2023.110715. Epub 2023 Sep 15. PMID: 37716419; PMCID: PMC10606955. 11: Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, León F, Sharma A, McMahon LR, Avery BA, McCurdy CR. Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. J Nat Prod. 2021 Apr 23;84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. Epub 2021 Feb 23. PMID: 33620222; PMCID: PMC8694001. 12: Ameline A, Gheddar L, Arbouche N, Blanchot A, Raul JS, Kintz P. Testing for Kratom alkaloids in fingernail clippings - not only mitragynine. J Pharm Biomed Anal. 2024 Jun 15;243:116078. doi: 10.1016/j.jpba.2024.116078. Epub 2024 Mar 1. PMID: 38489958. 13: Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA. Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Aug;88(9-10):838-857. doi: 10.1055/a-1795-5876. Epub 2022 Apr 25. PMID: 35468648; PMCID: PMC9343938. 14: Teh JL, Abdul Rahman SF, Domnic G, Satiyasilan L, Chear NJY, Singh D, Mohana-Kumaran N. Rapid spheroid assays in a 3-dimensional cell culture chip. BMC Res Notes. 2021 Aug 13;14(1):310. doi: 10.1186/s13104-021-05727-0. PMID: 34389056; PMCID: PMC8361632. 15: Lee MJ, Ramanathan S, Mansor SM, Tan SC. Development of an ELISA for detection of mitragynine and its metabolites in human urine. Anal Biochem. 2020 Jun 15;599:113733. doi: 10.1016/j.ab.2020.113733. Epub 2020 Apr 14. PMID: 32302607. 16: Sharma A, Kamble SH, León F, Chear NJ, King TI, Berthold EC, Ramanathan S, McCurdy CR, Avery BA. Simultaneous quantification of ten key Kratom alkaloids in Mitragyna speciosa leaf extracts and commercial products by ultra-performance liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2019 Aug;11(8):1162-1171. doi: 10.1002/dta.2604. Epub 2019 May 15. PMID: 30997725; PMCID: PMC7927418. 17: Zhang M, Sharma A, León F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ. Plant growth and phytoactive alkaloid synthesis in kratom [Mitragyna speciosa (Korth.)] in response to varying radiance. PLoS One. 2022 Apr 26;17(4):e0259326. doi: 10.1371/journal.pone.0259326. PMID: 35472200; PMCID: PMC9041851. 18: Sengnon N, Vonghirundecha P, Chaichan W, Juengwatanatrakul T, Onthong J, Kitprasong P, Sriwiriyajan S, Chittrakarn S, Limsuwanchote S, Wungsintaweekul J. Seasonal and Geographic Variation in Alkaloid Content of Kratom (Mitragyna speciosa (Korth.) Havil.) from Thailand. Plants (Basel). 2023 Feb 19;12(4):949. doi: 10.3390/plants12040949. PMID: 36840297; PMCID: PMC9966779. 19: Gutridge AM, Robins MT, Cassell RJ, Uprety R, Mores KL, Ko MJ, Pasternak GW, Majumdar S, van Rijn RM. G protein-biased kratom-alkaloids and synthetic carfentanil-amide opioids as potential treatments for alcohol use disorder. Br J Pharmacol. 2020 Apr;177(7):1497-1513. doi: 10.1111/bph.14913. Epub 2020 Jan 24. PMID: 31705528; PMCID: PMC7060366. 20: Tanna RS, Nguyen JT, Hadi DL, Manwill PK, Flores-Bocanegra L, Layton ME, White JR, Cech NB, Oberlies NH, Rettie AE, Thummel KE, Paine MF. Clinical Pharmacokinetic Assessment of Kratom (Mitragyna speciosa), a Botanical Product with Opioid-like Effects, in Healthy Adult Participants. Pharmaceutics. 2022 Mar 11;14(3):620. doi: 10.3390/pharmaceutics14030620. PMID: 35335999; PMCID: PMC8950611.