Akuammine

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

MedKoo CAT#: 592395

CAS#: 3512-87-6

Description: Akuammine is an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds.


Chemical Structure

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Akuammine
CAS# 3512-87-6

Theoretical Analysis

MedKoo Cat#: 592395
Name: Akuammine
CAS#: 3512-87-6
Chemical Formula: C22H26N2O4
Exact Mass: 382.19
Molecular Weight: 382.460
Elemental Analysis: C, 69.09; H, 6.85; N, 7.32; O, 16.73

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.