Speciociliatin | CAS#14382-79-7 | mitragynine diastereomer

MedKoo Cat#: 145348 | Name: Speciociliatin

Description:

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

Speciociliatine, a diastereomer of mitragynine, is an indole-based alkaloid found in kratom. Speciociliatine has been found to be a major circulating alkaloid in humans following oral administration of a kratom product. The metabolism of speciociliatine is predominantly mediated by CYP3A4 with minor contributions by CYP2D6.

Chemical Structure

Speciociliatin

CAS#14382-79-7

Theoretical Analysis

MedKoo Cat#: 145348

Name: Speciociliatin

CAS#: 14382-79-7

Chemical Formula: C23H30N2O4

Exact Mass: 398.2206

Molecular Weight: 398.50

Elemental Analysis: C, 69.32; H, 7.59; N, 7.03; O, 16.06

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Speciociliatin; Speciociliatine;

IUPAC/Chemical Name

methyl (E)-2-((2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate

InChi Key

LELBFTMXCIIKKX-MYLQJJOTSA-N

InChi Code

1S/C23H30N2O4/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/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-/m1/s1

SMILES Code

[H][C@]12C[C@@H]([C@H](CC)CN1CCC3=C2NC4=C3C(OC)=CC=C4)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 398.50 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: Kamble SH, Berthold EC, Kanumuri SRR, King TI, Kuntz MA, León F, Mottinelli M, McMahon LR, McCurdy CR, Sharma A. Metabolism of Speciociliatine, an Overlooked Kratom Alkaloid for its Potential Pharmacological Effects. AAPS J. 2022 Jul 19;24(5):86. doi: 10.1208/s12248-022-00736-8. PMID: 35854066; PMCID: PMC9932950. 2: Berthold EC, Kamble SH, Raju KS, King TI, Popa R, Sharma A, León F, Avery BA, McMahon LR, McCurdy CR. Preclinical pharmacokinetic study of speciociliatine, a kratom alkaloid, in rats using an UPLC-MS/MS method. J Pharm Biomed Anal. 2021 Feb 5;194:113778. doi: 10.1016/j.jpba.2020.113778. Epub 2020 Nov 21. PMID: 33277117. 3: Hughs M, Kish-Trier E, O'Brien A, McMillin GA. Analysis of Mitragynine and Speciociliatine in Umbilical Cord by LC-MS-MS for Detecting Prenatal Exposure to Kratom. J Anal Toxicol. 2023 Jan 24;46(9):957-964. doi: 10.1093/jat/bkac064. PMID: 36047661. 4: Damodaran T, Chear NJ, Murugaiyah V, Mordi MN, Ramanathan S. Comparative Toxicity Assessment of Kratom Decoction, Mitragynine and Speciociliatine Versus Morphine on Zebrafish (Danio rerio) Embryos. Front Pharmacol. 2021 Aug 20;12:714918. doi: 10.3389/fphar.2021.714918. PMID: 34489704; PMCID: PMC8417521. 5: 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. 6: Philipp AA, Wissenbach DK, Weber AA, Zapp J, Maurer HH. Metabolism studies of the Kratom alkaloid speciociliatine, a diastereomer of the main alkaloid mitragynine, in rat and human urine using liquid chromatography-linear ion trap mass spectrometry. Anal Bioanal Chem. 2011 Mar;399(8):2747-53. doi: 10.1007/s00216-011-4660-9. Epub 2011 Jan 20. PMID: 21249338. 7: Helander A, Rylski A. Drug testing for mitragynine and kratom: Analytical challenges and medico-legal considerations. Drug Test Anal. 2023 Feb;15(2):213-219. doi: 10.1002/dta.3391. Epub 2022 Nov 4. PMID: 36258649; PMCID: PMC10098727. 8: Trager WF, Phillipson JD, Beckett AH. Chemical confirmation for the configurations assigned to the indole alkaloids, speciogynine, speciociliatine, mitraciliatine and hirsutine. Tetrahedron. 1968 Mar;24(6):2681-5. doi: 10.1016/s0040-4020(01)82542-4. PMID: 5641278. 9: Karunakaran T, Ngew KZ, Zailan AAD, Mian Jong VY, Abu Bakar MH. The Chemical and Pharmacological Properties of Mitragynine and Its Diastereomers: An Insight Review. Front Pharmacol. 2022 Feb 24;13:805986. doi: 10.3389/fphar.2022.805986. PMID: 35281925; PMCID: PMC8907881. 10: Basiliere S, Kerrigan S. Identification of metabolites and potential biomarkers of kratom in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Mar 1;1140:121971. doi: 10.1016/j.jchromb.2020.121971. Epub 2020 Jan 11. PMID: 32058315. 11: 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. 12: Lee CM, Trager WF, Beckett AH. Corynantheidine-type alkaloids. II. Absolute configuration of mitragynine, speciociliatine, mitraciliatine and speciogynine. Tetrahedron. 1967 Jan;23(1):375-85. doi: 10.1016/s0040-4020(01)83323-8. PMID: 6037287. 13: 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. 14: 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. 15: 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. 16: 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. 17: 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. 18: Domnic G, Jeng-Yeou Chear N, Abdul Rahman SF, Ramanathan S, Lo KW, Singh D, Mohana-Kumaran N. Combinations of indole based alkaloids from Mitragyna speciosa (Kratom) and cisplatin inhibit cell proliferation and migration of nasopharyngeal carcinoma cell lines. J Ethnopharmacol. 2021 Oct 28;279:114391. doi: 10.1016/j.jep.2021.114391. Epub 2021 Jul 2. PMID: 34224811. 19: 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. 20: Flores-Bocanegra L, Raja HA, Graf TN, Augustinović M, Wallace ED, Hematian S, Kellogg JJ, Todd DA, Cech NB, Oberlies NH. The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids. J Nat Prod. 2020 Jul 24;83(7):2165-2177. doi: 10.1021/acs.jnatprod.0c00257. Epub 2020 Jun 29. PMID: 32597657; PMCID: PMC7718854.