AKUAMMIGINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O3
Molecular Weight	352.4269
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@H]3C[C@H]12

InChI

InChIKey=GRTOGORTSDXSFK-BMYCAMMWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H24N2O3
Molecular Weight	352.4269
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6091834 | http://kratomguides.com/akuamma-seeds-positive-negative-effects/ | https://www.ncbi.nlm.nih.gov/pubmed/3021076 | http://www.zobodat.at/pdf/PHY_36_2_0185-0196.pdf

Akuammigine is an oxindole alkaloid. Akuammigine shows antiadrenergic activity and thus reduces heart rate.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-2c adrenergic receptor 44 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902 \|	Antagonist 2849	28.0 nM [Ki]
Alpha-2a adrenergic receptor 70 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902 \| https://www.ncbi.nlm.nih.gov/pubmed/6091834	Antagonist 2849	106.0 nM [Ki]
Alpha-2b adrenergic receptor 35 Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Antagonist 2849	116.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Protozoal diseases 1 Sources: https://www.google.com/patents/US5290553	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Selectivity of raubasine stereoisomers for alpha 1- and alpha 2-adrenoceptors in the rat.	1986-08	3021076
Effects of raubasine stereoisomers on pre- and postsynaptic alpha-adrenoceptors in the rat vas deferens.	1984-10	6091834

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Akuammigine (5 x 10-6 to 10-4 M) caused a parallel displacement to the right of the concentration-response curves to noradrenaline, without depressing the maximal contraction, except for akuammigine at 10-4 M.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:00:35 GMT 2025` Edited by `admin` on `Mon Mar 31 23:00:35 GMT 2025`
Record UNII	1E21YYE0UM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4H-INDOLO(2,3-A)PYRANO(3,4-G)QUINOLIZINE-1-CARBOXYLIC ACID, 4A,5,7,8,13,13B,14,14A-OCTAHYDRO-4-METHYL-, METHYL ESTER, (4S,4AS,13BR,14AS)-

Preferred Name

English

AKUAMMIGINE

Common Name

English

OXAYOHIMBAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-19-METHYL-, METHYL ESTER, (3.BETA.,19.ALPHA.,20.ALPHA.)-

Common Name

English

Code System Code Type Description

CHEBI

141878