Akuammigine

Catalog Number	ACM642171
CAS Number	642-17-1
Synonyms	(3β,20α)-16,17-Didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid methyl ester
Molecular Weight	352.4
InChI	InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19+/m0/s1
InChI Key	GRTOGORTSDXSFK-BMYCAMMWSA-N
Melting Point	122-124 °C
Purity	95%+
Complexity	606
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
Exact Mass	352.17869263
Heavy Atom Count	26
Hydrogen Bond Acceptor Count	4
Hydrogen Bond Donor Count	1
Isomeric SMILES	C[C@H]1[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45
Monoisotopic Mass	352.17869263
PhysicalState	Powder
Rotatable Bond Count	2
Topological Polar Surface Area	54.6 Ų

Case Study

Study on the Anti-Inflammatory and Analgesic Effects of Pseudo-Akuammigine Alkaloids

Duwiejua, M., E. et al. Journal of Ethnopharmacology, 2022, 81(1), 73-79.

Pseudo-akuammigine is an alkaloid derived from Picralima nitida seed extract. The anti-inflammatory and analgesic effects of ψ-akuammigine were studied through carrageenan-induced rat paw edema and rat tail flick. The results showed that ψ-akuammigine has anti-inflammatory and analgesic effects.
Anti-inflammatory and analgesic effects
· When administered at 1.0, 5.0 and 50 mg kg-1 , p.o. before the induction of oedema, ψ-akuammigine significantly (P < 0.05) reduced the maximal oedema response attained during 6 h to 78.29±2.1, 74.79±4.3 and 59.59±2.3% of the inflamed control response respectively. A dose-dependent inhibitory effect was observed on carrageenan-induced rat paw edema over a range of doses.
· On molar basis, ψ-akaummigine was 3.5 times and 1.6 times less potent than morphine and indomethacin respectively as an analgesic. The ED50 values were 2.9, 10 and 6.3 mM for morphine, ψ-akaummigine and indomethacin respectively. Attenuation of the analgesic action of c-akuammigine by naloxone indicated an interaction with opioid receptors in vivo. It is also possible that ψ-akuammigine relieves pain by blocking the activity of a pronociceptive/hyperalgesic endogenous substance.

Synthesis of Heteroyohimbine Alkaloids Incluidng Akuummigine

SAKAI, SHINICHIRO, et al. Chemical and Pharmaceutical Bulletin, 1978, 26(8), 2596-2598.

The synthesis of heteroyohimbine alkaloids, akuammigine(12) and its 19-epimer 3-isorauniticine (11) has been reported in this work.
General procedure for synthesis
· Demethylation of 3 with acetone-HCl gas gave desmethylhirsuteine (4, mp 180-182° in 87%, yield, which was oxidized with m-chloroperbenzoic acid (m-CPBA) in CHCl3 to give desmethylhirsuteine N-oxide (5, mp 209-211°).
· The modifed Polonovski reaction of 5 was accomplished in excess trifuoroacetic anhydride in CH2Cl2 under cooling with dry ice- acetone. The reaction products were reduced with NaCNBHs in dimethylformamide and phosphate buffer solution at pH 5 (1:1 v/v) for 4 hr.
· Chromatography of the reaction products on alumina gave an amorphous compound A (HCl salt, mp 280-281°) in 4% yield as the first eluant. Through analysis of the spectral data, the structure of A was assumed to be 11, and direct comparison of A with real samples of 3-isosineine (11) demonstrated their complete identity (infrared (IR), mass and Circular dichroism (CD) spectrum).
· The second product was an amorphous heteroyohimbine B (11%) which showed the same IR, 1HNMR, mass and CD spectra with those of an authentic akuammigine (12).

Custom Q&A

What is the chemical formula of Akuammigine?

The chemical formula of Akuammigine is C21H24N2O3.

What is the molecular weight of Akuammigine?

The molecular weight of Akuammigine is 352.43.

What is the melting point of Akuammigine?

The melting point of Akuammigine is 122-124 °C.

From which plants is Akuammigine isolated?

Akuammigine is isolated from Vinca sardoa and Uncaria rhynchophylla.

What is the role of Akuammigine as per ChEBI definition?

Akuammigine has a role as a plant metabolite.

What is the predicted boiling point of Akuammigine?

The predicted boiling point of Akuammigine is 524.0±50.0 °C.

What is the predicted density of Akuammigine?

The predicted density of Akuammigine is 1.30±0.1 g/cm3.

What is the pka value of Akuammigine?

The pka value of Akuammigine is 18.03±0.60.

What is another name for Akuammigine?

Another name for Akuammigine is Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester.

What type of compound is Akuammigine?

Akuammigine is a monoterpenoid indole alkaloid, a methyl ester, and an organic heteropentacyclic compound.

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