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MedKoo Cat#: 592395 | Name: Akuammine

Description:

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

Akuammine is an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds.

Chemical Structure

Akuammine
Akuammine
CAS#3512-87-6

Theoretical Analysis

MedKoo Cat#: 592395

Name: Akuammine

CAS#: 3512-87-6

Chemical Formula: C22H26N2O4

Exact Mass: 382.1893

Molecular Weight: 382.46

Elemental Analysis: C, 69.09; H, 6.85; N, 7.32; O, 16.73

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 #
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Synonym
Akuammine
IUPAC/Chemical Name
Akuammine
InChi Key
YILKZADAWNUTTB-QLWRWLBVSA-N
InChi Code
InChI=1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4-/t15-,18-,20-,21-,22+/m0/s1
SMILES Code
COC([C@]12CO[C@]34[C@@H]5C[C@H]1/C(CN5CC[C@]23c6c(N4C)ccc(O)c6)=C\C)=O
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 382.46 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: Moreno J, Picazo E, Morrill LA, Smith JM, Garg NK. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A. J Am Chem Soc. 2016 Feb 3;138(4):1162-5. doi: 10.1021/jacs.5b12880. Epub 2016 Jan 19. PubMed PMID: 26783944; PubMed Central PMCID: PMC5154302. 2: Menzies JR, Paterson SJ, Duwiejua M, Corbett AD. Opioid activity of alkaloids extracted from Picralima nitida (fam. Apocynaceae). Eur J Pharmacol. 1998 May 29;350(1):101-8. PubMed PMID: 9683021. 3: Kapadia GJ, Angerhofer CK, Ansa-Asamoah R. Akuammine: an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds. Planta Med. 1993 Dec;59(6):565-6. PubMed PMID: 8302957. 4: Lewin G, Le Ménez P, Rolland Y, Renouard A, Giesen-Crouse E. Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors. J Nat Prod. 1992 Mar;55(3):380-4. PubMed PMID: 1317407. 5: Balsevich J, Constabel F, Kurz WG. Alkaloids of Vinca major cv. Variegata. Planta Med. 1982 Feb;44(2):91-3. PubMed PMID: 17402086. 6: JANOT MM, LE MEN J, AGHORAMURTHY K, ROBINSON R. The identity of vincamajoridine and akuammine. Experientia. 1955 Sep 15;11(9):343. PubMed PMID: 13262018.