ACONITINE HYDROBROMIDE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H47NO11.BrH
Molecular Weight	726.649
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Br.CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)[C@H]4[C@@H]1[C@@]3([C@@H]5C[C@@]6(O)[C@H](OC(=O)C7=CC=CC=C7)[C@@H]5[C@]4(OC(C)=O)[C@@H](O)[C@@H]6OC)[C@H](C[C@H]2O)OC

InChI

InChIKey=QKBOPFIDNJPMBP-PHFVEKHWSA-N

InChI=1S/C34H47NO11.BrH/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33;/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3;1H/t19-,20-,21+,22-,23+,24+,25-,26-,27+,28-,29+,31+,32-,33+,34-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C34H47NO11
Molecular Weight	645.7371
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://abcdef.uni-hd.de/institute/fak14/ipmb/phazb/pubwink/1998/15.%201998.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7839574 | https://www.ncbi.nlm.nih.gov/pubmed/8082861

Aconitine is an alkaloid found in the Aconitum species. Aconitine is a highly toxic cardiotoxin and neurotoxin. In China and other countries, the herbal extract containing aconitine was used for the treatment of pain in musculoskeletal disorders, however the safety margin between therapeutic analgesic effect of aconitine and its known cardiotoxic effect is so narrow that the treatment may cause poisoning and death. The mechanism of aconitine action is explained by its ability to activate voltage-dependent sodium-ion channels.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-dependent sodium-ion channels 3 Target ID: Voltage-dependent sodium-ion channels Sources: http://abcdef.uni-hd.de/institute/fak14/ipmb/phazb/pubwink/1998/15.%201998.pdf	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Musculoskeletal disorders 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8082861	Palliative		Not Provided 511	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961 OCT2 779 OAT1 725 Nav1.5 116 Cav1.2 58 Kv1.5 27	OATP1B1 503 OATP1B3 435 OATP2B1 122 OCT1 393 OCT3 92 OAT3 391 P-gp 2052 BCRP 697 MRP2 252 CYP3A5 446 CYP1A2 1197 CYP2C8 810 CYP2C19 1119 CYP2E1 729	P-gp 301

Drug as perpetrator

Target	Modality	Activity
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20448812/	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20448812/	weak [IC50 >100 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21561794/	weak
Kv1.5 42	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20600762/	yes [IC50 0.796 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23770354/	yes [IC50 59.2 uM]
P-gp 1932	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/27139035/	yes
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27139035/	yes

Drug as victim

Target	Modality	Activity
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	major
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	major
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	major
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	minor
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21277363/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23200901/	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23200901/ \| https://pubmed.ncbi.nlm.nih.gov/23562926/	yes
OAT3 391	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
OATP1B1 503	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
OATP1B3 435	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
OATP2B1 122	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
OCT1 393	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
OCT3 92	substrate 4014 Sources: https://pubs.rsc.org/en/content/articlehtml/2019/ra/c9ra00393b	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23200901/ \| https://pubmed.ncbi.nlm.nih.gov/23562926/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 63	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/28056022/
Nav1.5 119	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/28056022/
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/28056022/ \| https://pubmed.ncbi.nlm.nih.gov/20600762/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2430	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2430
eMolecules	26424222	https://www.emolecules.com/cgi-bin/more?vid=26424222
MolPort	MolPort-002-527-310	https://www.molport.com/shop/molecule-link/MolPort-002-527-310

PubMed

Title	Date	PubMed
Antillatoxin is a sodium channel activator that displays unique efficacy in heterologously expressed rNav1.2, rNav1.4 and rNav1.5 α subunits.	2010-12-14	21156065
Aconitine blocks HERG and Kv1.5 potassium channels.	2010-08-19	20600762
[Difference of hypaconitine concentration in serum between cold-deficiency and normal mice].	2010-08	20931857
The histone deacetylase inhibitor suberoylanilide hydroxamic acid reduces cardiac arrhythmias in dystrophic mice.	2010-07-01	20164117
[Evaluation of the accumulation of dry substance and active componentsevaluation of the accumulation of dry substance and active components of Radix Aconiti Lateralis Praeparata].	2010-04	20845771
Nicotinic antagonist effects in the mediodorsal thalamic nucleus: regional heterogeneity of nicotinic receptor involvement in cognitive function.	2009-10-01	19477167
Stability-indicating reversed-phase liquid chromatographic methods for the determination of aconitine and piperine in a polyherbal formulation.	2009-09-01	19714970
Serum elimination profiles of methyllycaconitine and deltaline in cattle following oral administration of larkspur (Delphinium barbeyi).	2009-07	19566479
Role of M3 receptor in aconitine/barium-chloride-induced preconditioning against arrhythmias in rats.	2009-05	19043693
Studies on the aconitine-type alkaloids in the roots of Aconitum Carmichaeli Debx. by HPLC/ESIMS/MS(n).	2009-03-15	19159802
[The role of reflexotherapy and physical training in the combined treatment and the prevention of paroxysmal form of idiopathic atrial fibrillation].	2009-01-30	19175054
Nicotine induces cell proliferation, invasion and epithelial-mesenchymal transition in a variety of human cancer cell lines.	2009-01-01	18844224
Nicotinic acetylcholine alpha4beta2 receptor regulates the motivational effect of intracranial self stimulation behavior in the runway method.	2008-12	19057129
Effects of aconitine on [Ca2+] oscillation in cultured myocytes of neonatal rats.	2008-10	18846325
Daphniphyllum and diterpenoid alkaloids from Daphniphyllum longeracemosum.	2008-07	18553922
Characterization of aconitine-induced block of delayed rectifier K+ current in differentiated NG108-15 neuronal cells.	2008-05	18336846
Differential coupling of M1 muscarinic and alpha7 nicotinic receptors to inhibition of pemphigus acantholysis.	2008-02-08	18073210
The beta-amyloid protein of Alzheimer's disease binds to membrane lipids but does not bind to the alpha7 nicotinic acetylcholine receptor.	2007-06	17286584
Combinative method using HPLC quantitative and qualitative analyses for quality consistency assessment of a herbal medicinal preparation.	2007-01-04	16920317
Characterization of metabolites and cytochrome P450 isoforms involved in the microsomal metabolism of aconitine.	2006-12-05	16949890
Evaluation of the role of nicotinic acetylcholine receptor subtypes and cannabinoid system in the discriminative stimulus effects of nicotine in rats.	2006-07-01	16730696
Effects of chronic administrations of aconitine on body weight and rectal temperature in mice.	2006-04-21	16293382
Electrophysiological mechanisms of atrial flutter.	2006-04-01	16943903
Nicotine reverses consolidated long-term potentiation in the hippocampal CA1 region.	2006-03-17	16564510
Effects of processed Aconiti tuber and its ingredient alkaloids on the development of antinociceptive tolerance to morphine.	2006-02-20	16169697
Simultaneous determination of six Aconitum alkaloids in proprietary Chinese medicines by high-performance liquid chromatography.	2005-11-04	16233884
Methyllycaconitine prevents methamphetamine-induced effects in mouse striatum: involvement of alpha7 nicotinic receptors.	2005-11	16076935
Effects of alpha4beta2 and alpha7 nicotinic acetylcholine receptor antagonists on place aversion induced by naloxone in single-dose morphine-treated rats.	2005-09-05	16098507
[Effects of different penetration enhancers on percutaneous absorption of lappaconitine gel in vitro].	2005-05	16075728
A QSAR toxicity study of a series of alkaloids with the lycoctonine skeleton.	2004-12-31	18007512
The rat spinal cord slice: Its use in generating pharmacological evidence for cholinergic transmission using the alpha7 subtype of nicotinic receptors in the central autonomic nucleus.	2004-08-25	15862469
Nicotine improves sustained attention in mice: evidence for involvement of the alpha7 nicotinic acetylcholine receptor.	2004-05	14970827
[The ion targets of arrhythmias induced by ouabain and aconitine in guinea pig and rat ventricular myocytes].	2004-05	15338872
[Emergency treatment of 4 patients with acute severe intoxication of radix aconiti ferus].	2004-03	15074107
Carbamoylcholine homologs: novel and potent agonists at neuronal nicotinic acetylcholine receptors.	2003-10	14500743
Characterization of aconitine-type alkaloids in the flowers of Aconitum kusnezoffii by electrospray ionization tandem mass spectrometry.	2003-09	14505324
[Anti-arrhythmia activity of estradiol valerate and estradiol nitrate].	2003-08-20	12924228
Contribution of functional voltage-gated Na+ channel expression to cell behaviors involved in the metastatic cascade in rat prostate cancer: I. Lateral motility.	2003-06	12704658
[Role of ORL1 receptors in the regulation of cardiac resistance to arrhythmogenic effects ].	2003-04	12966717
Evidence suggesting that the mouse sperm acrosome reaction initiated by the zona pellucida involves an alpha7 nicotinic acetylcholine receptor.	2003-04	12606407
Effect of garlic on cardiovascular disorders: a review.	2002-11-19	12537594
[Study on metabolites on aconitine in rabbit urine].	2002-10	12567861
[The analysis of Aconitum by FTIR].	2002-08	12938376
Synaptic potentials mediated by alpha 7 nicotinic acetylcholine receptors in supraoptic nucleus.	2002-01-01	11756485
Acute aconitine poisoned patients with ventricular arrhythmias successfully reversed by charcoal hemoperfusion.	2002-01	11781926
[Antiarrhythmic drug allapinin: review of results of clinical investigation].	2002	12494120
The nicotinic antagonist methyllycaconitine has differential effects on nicotine self-administration and nicotine withdrawal in the rat.	2001-11	11694204
Dorsal root ganglion neurons express multiple nicotinic acetylcholine receptor subtypes.	2001-10	11600638
Acute and chronic nicotine exposure reverse age-related declines in the induction of long-term potentiation in the rat hippocampus.	2001-03-16	11251214
Antiarrhythmic properties of 5-(3-tert-butylamino-2-hydroxy)propoxy-3,4-dihydrocarbostyril hydrochloride (OPC-1085), a newly synthesized, potent beta-adrenoreceptor antagonist.	1977-11-01	22416

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

When added at concentration of 3 uM, aconitine depolarized rat ventromedial hypothalamic neurons.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:41:32 GMT 2025` Edited by `admin` on `Mon Mar 31 22:41:32 GMT 2025`
Record UNII	US306163EJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACONITINE HYDROBROMIDE

Common Name

English

ACONITINE HYDROBROMIDE ANHYDROUS

Preferred Name

English

ACONITINE HYDROBROMIDE ANHYDROUS [MI]

Common Name

English

ACONITANE-3,8,13,14,15-PENTOL, 20-ETHYL-1,6,16-TRIMETHOXY-4-(METHOXYMETHYL)-, 8-ACETATE 14-BENZOATE, HYDROBROMIDE (1:1), (1.ALPHA.,3.ALPHA.,6.ALPHA.,14.ALPHA.,15.ALPHA.,16.BETA.)-

Systematic Name

English

Code System Code Type Description

FDA UNII

US306163EJ